How To Have an Unforgettable one night Stand: From Pickup to Aftercare

There are one night stands you forget before you've brushed your teeth — and there are one night stands you're still thinking about years later. Today we're breaking down the difference.

Zachary Zane — author of Boy Slut, Men's Health sex columnist, and Grindr's official sex and relationship expert — joins me to map out exactly how to have a one night stand that actually lives up to the fantasy. From the mental prep most people skip, to where to find the right person, to what happens in the room that makes it unforgettable — we're covering every stage.

We get into: 

→ The honest conversation you need to have with yourself before you go out 
→ Where to find casual sex based on your gender, orientation, and vibe 
→ How to communicate what you want without killing the momentum 
→ Why one night stands can be MORE intimate than relationship sex 
→ The aftercare that turns a hookup into a core memory instead of a regret 
→ Safety tips every woman needs before leaving with a stranger

Plus — we both share our own one night stand stories, because we've been there. A lot.

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Transcript

Rebrand And What This Show Is

SPEAKER_02 0:53

Do the sex.

What Makes A One Night Stand Last

SPEAKER_01 0:54

I'm Annette Benedetti, host of the podcast formerly known as Locker Room Talk and Shots. The show has a new name, Talk Sex with Annette. But at its core, this is still your locker room. It's where we strip away shame, get curious, and speak the unspoken about sex, kink dating, pleasure, and desire. Around here, nothing's off limits. These are the kinds of conversations we save for our boldest group chat, our most trusted friends, and of course, the women's locker room. Think raw, honest, and sometimes unapologetically raunchy. Welcome to my podcast where desire meets disruption and pleasure becomes power. Let's talk about sex. Cheers. Today's talk Sex with Annette topic is the anatomy of an unforgettable one-night stand. There are one night stands you forget before you've even brushed your teeth. And there are one night stands you're still thinking about years later, the ones that changed what you thought sex could feel like with someone you barely know. Today we are discussing the difference. What are the actual ingredients of a one-night stand that stays with you? Not the positions and not the chemistry, the specific things that happen in the room and in your head that made it unforgettable. We're talking about presence, desire, generosity, and communication with someone whose last name you may not even know, and why most casual sex falls so far short of what's possible. My guest is Zachary Zane, the author of Boy Slet, a memoir and manifesto, men's health sex plain it columnist, grinders official sex and relationship expert, and one of the sharpest voices on casual sex hookup culture and what actually makes sex good. Thank you for joining me today, Zach. Before we dive in, I gotta remind you that I'm over on OnlyFans and There. I'm sharing my sex and intimacy, how-tos demos, and audio guided self-pleasure meditations. You can find me there and on Substack with my handle at TalkSexWithanet, or you can find both Zach and I by scrolling down to the notes section below where I'm gonna be leaving links to wherever you want to find both of us. But for now, Zach, will you tell my listeners just a little bit more about you?

SPEAKER_00 3:15

Yeah, sure. So I'm a sexual relationship. I've written for New York Times, Rolling Stone, Washington Post, GQ. I write a lot about casual sex, which is why I'm here today. A lot about your identity and bisexuality, pinks, and non-monogamy. And as you mentioned, I'm also the sexual relations expert for Grinder as well, which has been obviously a lot of fun.

SPEAKER_01 3:37

So he's an expert, folks. Like tried and true. A lot of people trust his advice. What I also love about this conversation for us and for my listeners is we are both outspoken bisexual folks.

SPEAKER_00 3:51

Yes, we are. I love that.

SPEAKER_01 3:53

And so we both had, I would assume, a generous amount of casual sex with people of all genders.

SPEAKER_00 4:00

Sure have.

Plan Ahead Or Go Opportunistic

SPEAKER_01 4:02

So I think that's gonna give us some unique insight to give all of my listeners, regardless of gender or orientation, on what casual sex can look like for you. I am ready to talk about this, guys. You're gonna want to stay to the end because this conversation is an arc. It's really going to help you set things up from prior to even heading out to execution and post-casual hookup. How to make it the best possible and get everything you want out of it. Maybe you'll want to make it a lifestyle. Who knows? But we're gonna give you those tools and of course the takeaways at the end. So let's dive in. I'm ready to talk about how to have the most incredible one night stand of your life. Let's do that. Cheers. Cheers. First question. When should you start thinking about or considering your one night stand? Do you start before you even go out? Is it in the moment? If you're wanting to set yourself up for an optimal one night stand, I think I think it can be both.

SPEAKER_00 5:12

I think it can be opportunistic. You happen to be out and someone that you connect with, you're attracted to them, and you didn't have the intention of having a one-night stand or going home with someone that night, but because that connection was so strong, you're like, oh yeah, I definitely want to do this. But I would argue that most of the time it is relatively planned. You want to feel and look your best. You want to be your sexiest. Like I wear my sexy underwear when I go out because I I hope someone sees it. I make sure to shower if I I make sure to douche if I plan on having anal sex. And so because of that, I don't want to necessarily say you're you're manifesting, but you really are putting yourself in the headspace and doing everything right so you can feel as confident and sexy as possible. So that way you can go home with someone.

Motivation Shame And Emotional Readiness

SPEAKER_01 6:03

I love that because even if you don't go home with someone, you're gonna feel super charged going out and attractive, regardless of if you manifest that one night stand or not. I mean, exactly when. But I wonder this as I was listening to you talk is there some point ahead of time that you need to have a conversation with yourself and say, am I okay with having a one-night stand? Is this something I want to do in my life? So that because I think what happens is a lot of times people end up in one night stands and then there's this shame because they didn't expect it to happen, but there was an opportunity or someone they were attracted to, and they're like, and then I went home and I did that. Especially for women, I would argue probably, and you can correct me if I'm wrong. I think women carry that shame a little bit more typically. Right. And then they're like, I I I went home and I I slept with a stranger and blah, and I'm a terrible person. This means I'm a slut. It might be a good idea before you even go out to sit down with yourself and have a conversation. Am I okay with a one-night stand?

SPEAKER_00 7:12

Yeah, absolutely. So, yeah, if you've never had a one-night stand and you're considering it, I think it's worth considering why do you want this? Do you genuinely want this? We often talk about slut shaming, but I also think there's something as prude shaming, where especially if you have some sex positive friends, and don't get me wrong, sex positivity is not about the number of people you have sex with, it's having the type of sex you want to have with the people you want to have. And if that means you're asexual and having no sex, you're still sex positive, right? So I think, okay, is this place coming from a hey, I feel like everyone else is doing this and I'm not, and I'm doing this from a place of FOMO when genuinely you have no desire to do this, okay. Then I don't think you should do this. If you're coming to it from a place of, hey, I want to explore my sexuality a little bit more. I think this would be a fun and hot encounter. I think it'll be an experience that that I should hopefully enjoy. And and I and I want to genuinely do this. So I think analyzing where are your motivations coming from? Are they genuine? I think also thinking about what would happen. And again, it's hard to predict your emotions and how you feel. So you can do your best to plan how you're going to respond to something and might not know. But I think many of us do have a sense, what would happen if this goes awry? What happens if you feel used afterwards? What happened if you don't get off or they leave in the middle of the night? But whatever it is, and this does not go according to plan, how devastated will you be? Like, like if like I can have a shitty sexual encounter and brush it off. It's oh, that wasn't fun. That's not going to break my ego, that's not going to shatter me, that's not going to scourge me from having more casual encounters. I just know that wasn't great, and I can move on. But people have different relationships with sex. If you feel used after this and it doesn't go according to plan, you don't have the best time. How are you going to respond to this? How devastating will this actually be for you? Do you I guess what I'm asking you is do you think you can handle it if things go awry? And if you don't think you can, I I'd I'd really second guess whether you should be doing this or you should look for the means of, okay, well, how do I make myself feel comfortable if this doesn't go perfectly planned? But if you don't think you can handle it, then I wouldn't do it.

SPEAKER_01 9:36

Right. Really exploring that in your your mind ahead of time. And there's no way to know 100% until it happens. Of course. Being honest with yourself. What are my feelings around casual sex? Do I have some ideas that are really ingrained into me that are going to affect my sense of self-worth, right? For some people, that's there. And for other people, it's yeah, no, I don't. Sex doesn't, the sex I have does not affect my worth.

SPEAKER_00 11:01

If you have so much sexual shame and you're trying to almost combat it by having a slutty one-night stand, I do not think that's going to help. I think you need to first work on your sexual shame beforehand. Because otherwise, even if you have a great encounter, that shame is going to rear its ugly head and then ruin the encounter, even though, all things considered, it was a good one in the moment. So, like having casual sex is not going to solve your sexual shame or sex negativity that you've absorbed just from existing in a puritanical sex-negative society.

SPEAKER_01 11:35

And it's funny, even as you say the words casual sex, I can hear the negative connotation society has put on it, right? It's interesting, of course, for me, I don't internalize any of that, but it is something that a lot of people haven't done the same level work you and I have done or and aren't in sort of the work that we are in hear and feel, right? So if you haven't done work to take the shame away from the concept, maybe to help go dive in.

unknown 12:09

I know.

SPEAKER_00 12:10

I I almost wish it wasn't called casual sex. I wish it was just called a one-night stand, a one-time encounter, because I've had some casual sex, quote unquote, where I go home from some one bar, we never see them again. Let's say I'm on vacation. I feel like that's often where I have these one-night stands where I'm not going to necessarily see them again because I'm traveling. And they have been some of the most intimate, intense, rewarding, beautiful encounters that I would not describe as casual. What's casual about this, and again, that's not what the word casual means, even though we use it as a misnomer. What's casual is that I'm doing this once. But that's not what actually casual means. Doing it once means doing it once. But yeah, I think if you can separate, hey, casual sex is inherently meaningless because I'm only having it once, versus casual sex can be affirming and rewarding and pleasurable and just fun. That could maybe help you move to a place of, okay, I'm okay with having casual sex. Casual sex, yeah, doesn't mean devoids of meaning, doesn't mean you're treating your partners like shit, doesn't mean you're taking it not seriously. It just means I only plan to do this maybe once or a couple times, whatever it is. There's just no long-term potential for being with this person in a committed way.

SPEAKER_01 13:25

Yeah, and I think one night stands can be really transformative too. Like, especially if you're coming out of a dry spell or maybe a breakup or something like having a really awesome one night stand boy. I have one in college. I still think about I can't remember his name. I can't even remember his face, just that he was gorgeous and sweet. And it's so funny. I can't remember details, but I remember the event.

SPEAKER_00 13:53

Especially with people who are potentially a little bit avoidant, like avoidant personality types, like one night stand can actually be very freeing and liberating because there's not that pressure that this is going to be something more. And when you have that pressure that's in your head, you often will dissociate. You can't be in your body, you're not going to enjoy the sex. But that's why for me, some of the vacation sex I have is the absolute best sex I've ever had. And it's not just because I'm in a new space, it's not just because I've been relaxing and I'm not thinking about work. It's because I can appreciate this for what it is. I know this is not going anywhere. And there's, yeah, there's this level of safety and knowing that it's just this one-time thing. So let me just enjoy it. I don't have to overthink about this. So in that regard, it's it can be really yeah, affirming and beautiful, and you feel safer and just enjoy it more because there's not that pressure in your head of, oh, where is this going? Which typically take you out of sex.

SPEAKER_01 14:57

Vacation sex. That's a good time to have your one-night stand on vacation. I love it.

SPEAKER_02 15:02

That's my favorite.

SPEAKER_01 15:03

Yeah. Can you think of other before we get deeper into picking the person and how we work it out? We've done the mental setup, right? Make sure you've done some mental work before you launch into one night stands or casual sex. You're getting ready to go out and do it. You're gonna want to pull your stuff together, right? Take a shower, douche. Ladies, I don't know. It depends on what you want to do. I'm going to tighten up the shave job down there and in all places because that's my thing. I want to feel hot going out and be able to have my pick of my pick of the place, right? But also now let's talk about best opportunities for one night stands and casual sex. You mentioned vacation sex. Let's route just some other highlights to think about when might this be a good time. I mean, of course, any time is a fine time, but you know.

When One Night Stands Help

SPEAKER_00 15:56

It's yeah, I mean, let's just say if you're just feeling the right, it's more about the head space that you're in as opposed to necessarily what is like happening in your life. If you're in a headspace where you're you want to go out, you want to have this fun, you think it'll be connecting, it'll be good. I mean, sometimes one night stands, I've done it where I've just been stressed at work, and I just want to go out, and it is a I want to get a little drunk, I want to have sex, I want to be able to do this and just release some of that energy, release some of that stress, and then carry on with my work day the next day, feeling a little bit invigorated. Of course, relax and rest and all that. But I was gonna say, of course, be mindful of this. You don't want to use the other person, you don't want to use them as a human fleshlight, you know, immediately it's not just about you having sex. You come in two minutes and then you piece the fuck out of there. No, you're an asshole here. But I think there is a balance of, hey, I really want this for me to distress, and while still treating the other partner as a partner, as a human with respect, caring about their pleasure. So, yeah, for me, it can be a great way to distress, get out of my head, and have a little fun. So that's another time that I really enjoy it. This now really depends on the person and depends on the relationship you broke up from. There's always the common saying that the best way to get over a lover is to get under another. And I agree and disagree. I that is really a personal thing. It depends on the person, depends on how bad the breakup was. It depends on so many factors that are individual to you. But I can tell you, I've had times where after a breakup, I have loved casual sex and one night stands. And then there have been times where I'm like, I'm really too sad and I don't want to do this, and I have to wait many months so I'm in a place where I'm feeling horny and sexual again. So yeah, depending on the factors, depending on who you are, potentially it's good after a breakup, just to feel a little bit desired, just to get out of your head, to realize that they're, hey, there are other people who will find me attractive besides my partner. It's not just this all or nothing and no one's gonna love me, I'll never have sex again. But yeah, I think I'd be cautious and mindful. And if you maybe do get out there too quickly and have a casual sex a week after a long-term relationship and it doesn't go well, okay, then don't have it for now. Take a step back and reassess. That doesn't mean you can never have casual sex again. It means you did it at uh not the right time, right? So always being okay with being like, yeah, that didn't work for me. Let me take a step back, let me take a little break.

Where To Meet The Right Person

SPEAKER_01 18:29

I love it. All right. Where are we gonna go for an optimal one night stand? We want to find that person. We want we're in the mood, where are we going? And I I think both take turns with this one because I'm gonna tell you what I think the lady should do.

SPEAKER_00 18:44

I feel like I'll start with queer men. I feel like I rep grinder here, and I'd be amiss if I didn't say it's a great way to sexually connect with people. And you have guys on the app who are looking for a more committed relationship and more long-term stuff. You also have guys on the app that are more looking for casual sex, a one-night stand. I think grinder is whenever you want it to be. So just putting out your intentions. Hey, I'm looking for something more casual, I'm looking for a one-night stand and connecting with other people. But I think there are a lot of men on the app who are looking for the same thing that you are. So it's a really great way to expedite this process to meet someone who's seeking the same thing. So that's a great one. Uh I feel like it depends on your personality type. I think bars are still one of the most classic ways to do that. Some people I've met are really good at bars, they're really good at flirting with people, they're very confident, they uh they they know exactly what they're doing and they have a lot of success. I know people who feel very awkward, like going to a bar and getting picked up or picking someone up, but maybe that's not the space for you. If you are someone that is a little bit more awkward but can get there, maybe you're anxious when you go in. It's a new space, it's overwhelming. Make sure to not go to the bar and get hammered. Instead, I think really going with a hype man, going with a wingman, going with someone who you have that flirty, outgoing friend who knows how to strike a conversation with someone cute and then kind of hand it off to you and let them know, hey, the focus of this is I I need your help and in getting a one-night stand. So they're in on this, they know what's going on, they can help you. So thinking that this is not something you necessarily have to do alone or have to be a master flirter or just really confident, it's just have someone who can make you feel confident and go about doing that. Of course, there there are like sex parties uh in in sex spaces. I I love going to sex parties, I've been to mixed gender sex parties, I've been to all male sex parties, I've been to queer sex parties. And I want to emphasize that sex is not guaranteed at these spaces. You still have to flirt, you still have to have game. And I can tell my female friends, particularly to these spaces, and guys just come up to them. Do you want to book? It's the first thing they say, and they're like, no. Like, all you still have to get to know someone a little bit. But in sex spaces or sex club spaces, I would say it's much simpler to move that conversation to a place of sex because it is absolutely expected. Most of the people came there for that. You can move to a casual conversation to sex quicker than if you're at a bar or something like that. Often, don't worry, I've been to a bar, and sometimes if people talk to me within five sentences, like, you want to go back? And I'm like, Yeah, let's do it. But like most of the time, I'd say that's not necessarily the case. So I think finding sex parties is definitely one of the best way. There are a lot of swingers events if you're coupled again, and that's maybe I don't know if you would call it necessarily a one-night stand if you're a couple having sex with another couple or a partner, but you know, it might be a one-night stand and that you don't have sex with again. There's also a good sense of potentially community in swinger spaces. But yeah, finding the spaces using grind or using an app that facilitates that can help facilitate casual sex because other people are also looking for it too.

SPEAKER_01 23:01

Right. So I'm gonna speak for the women here because I do think the search for women versus men is a little different.

SPEAKER_00 23:09

Absolutely.

SPEAKER_01 23:12

And I love that you covered men looking for men and then men going out because it it does really depend on what you're looking for. And especially if you're a queer person and you're in the mood for one flavor or the other or a mix, then that's gonna really dictate where you go, right? So if I'm I'm like, I want to go out and get some dick tonight, that's gonna look different than if I'm like, I want to go hook up with a woman tonight. Absolutely. Totally different approach. I think for women, looking for men, I would I think the app is on my my three approaches. The app is on the list because it is. You can you can go through the app and pick up a guy. But I think if I want a one-night stand, I want to know that what I'm getting is like what I want. So me, I'm like a I like I like a one-night stand in a hotel, a nice hotel girly. I'm gonna go to a high-end hotel bar. I have to go by myself and I'm gonna sit up at the bar in the cutest little dress I have, looking casual, and all I have to do is wait for the guy that looks right to sit next to me and smile at him and start a conversation. One little funny one liner about something, and I'm gonna get a feel if he wants to talk or not, and then it's all go from there. So at least I might get shop a little. Now, if I go out to a dive bar and I can't be mad if I end up back in a room in a house that's like in an unmade bed or in his mom's garage. I'm gonna pick the kind of fuck I want based on where I'm going and knowing that it's it's a crapshoot at dive bar. You'll find somebody, but it's a crapshoot. In certain, I'm gonna weed out based on who can afford to be where. I also think sex clubs, that's a great idea too. As a woman, going as a single number one, you pay less. I think it's like$15 for a woman to get into sex clubs, and a guy, a single guy, has to pay like a hundred bucks. And then you also get to shop because again, you're gonna have your single men that are there, you're gonna have your couples that are there, and you get a shop around. But also everyone's there for sex. And the other thing I like is it's not, it's in a safe space, right? There's people around, there are rules built into sex club. So you're a little bit of them.

SPEAKER_00 25:40

They're like consent monitors where people are going around and just making sure no one's too inebriated, making sure someone's not being pushy, making sure someone, you know, is not joining a scene. You're already having sex with someone and someone tries to join, or someone is just staring at you from a foot away, they'll be like, hey, do you know these people? No, then you need to back up. So they they do have elements of protection in many of the spaces. And I think that's something you should steak out when doing that.

SPEAKER_01 26:07

Absolutely, absolutely. Now, as a woman trying to hook up and have a one-night stand with another woman, I cannot help you. I don't think any of us know how to do that. I'm gonna be honest with you. Uh queer men have it dialed in. Queer women, not so much. It is tough. You've got to either find a sex club where that's more queer-centered, which in Portland we do have one, or just find Sapphic party. There are more and more Sapphic play parties or dance parties. And there are even some yearly events that happen around the world in the US where you can meet other women. It's much harder. Women trying to have a one-night stand with another woman. That's rough, man. That's probably I would, I would, I would say it's more difficult than a man trying to have a one-night stand with a woman.

SPEAKER_00 26:57

It's I I I can't necessarily speak to that, but I have heard from so many female friends who are lesbian by queer that it's like they end up just sleeping with more men that because it's easier. Because there's such a like clearness, and they are down for casual sex if that's what they want. And so they struggle, they almost find themselves sleeping with more men, even though they don't want to, just because, for the reasons you said, it can be sometimes more challenging to find other lesbians, queer people that want the the same thing that you want more casually.

Safety Consent And Clear Intentions

SPEAKER_01 27:32

But I do want to say one thing for the women, and then you can speak to men. I want to bring up the safety factor for women too. If you are going to have a one-night stand, and I'm very lucky, I have a crew of women. So if one of us were out or we pick up a guy that we want to go home with or whatever, we help each other out. We let the person know that A, we're letting our friends know. I've even had a friend leaving the bar with a man and made him let me take a picture of his ID. I was like, I want to know that she's safe. So I want to know who you are before you take my friend home. But having some safety protocol in place is really important and not bringing them back to your place if possible. That's why I like a high-end hotel.

SPEAKER_00 28:12

Just handle it. One thing that I tell my friends to do, if they're not already doing this, most of my female friends are, is when you say before going home with someone, before meeting someone up, hold on, I'm texting my friend my location and letting them know where I'm going. And just by saying that, that can itself just be a big deterrent from men being predators, from men being abused, whatever it is. Again, it's not a foolproof plan. You should still have other safety precautions in place, but always being like, hold on, I'm texting my friend my location and where I am going. Hold on, I'm turning on find my location, I'm sharing it with multiple friends. That is a way to protect yourself. Yeah.

SPEAKER_01 28:50

Right. I've even said, oh, after I need to text my friend at this time just so they know I'm okay. And if any guy gets weird about that, then back the fuck out.

SPEAKER_00 29:02

Like what is redder than a red flag? That is a red flag covered in shift. Get out of it. Absolutely.

SPEAKER_01 29:09

Absolutely. Safety is super important. All right. So we've decided how we're going to pick up our person. Let's talk about going out, right? Now we met this person. I'm going to pretend like I'm at the bar at the high-end bar. And we've been talking. We want to make sure, and you did bring up earlier, and we need to like really make this clear. It has to be a consensual one night stand. It's not someone tricking someone else into having sex thinking that maybe this is going to turn into something, right? That's not cool. You got to be up front. We're not doing that to people because that's shitty, right? One night stands are completely ethical.

SPEAKER_00 29:45

It's it's it's tough to somewhat navigate that because you don't want to immediately be like, oh, I don't see this going anywhere. This is going to be one I think you can't say like that. But I think there are certain more subtle ways to communicate that you could say, hey, I, you know what, I'm out just looking to have fun tonight.

SPEAKER_01 30:01

I think that's better. It's harder for men, but will not deter a dude.

SPEAKER_00 30:05

Yeah. So I'm just looking, I'm having a fun night out, something that conveys ethically and nicely without being like an asshole that you don't see this going anywhere.

SPEAKER_01 30:15

And here's this is how I do everything in life. If I'm gonna say something I think someone may not like as much, I always start with something that they are gonna like, tell them the thing they aren't gonna like, and then give them something they're gonna like. I think it's a nice sandwich. And I want the same for myself. So it's oh my God, you're so fucking sexy. And I I really want to spend time with you tonight. I want to be honest. I'm not looking for anything. I'm not looking to date. But if that's okay with you and you're feeling the vibe, I'd like to see what the night can do for us.

SPEAKER_00 30:50

Love that. Love that. I think it's easier for a woman to say that than a man. Absolutely. I think a man might come off like a douchebag. Still, I think there are ways to do it that again, I still have to think about that. I like, yeah, my gut response was some I somehow to convey this, but I'm not exactly sure what it is, but it's hard. Yeah.

SPEAKER_01 31:11

I also like I'm like I go back and forth with you because I'm like thinking as a woman, like honestly, for me, if a guy comes up and we're talking and it's going well and he tells me I'm hot, but also he's not looking for anything, but he wants to have fun for the night, I'm gonna be like, dude, that sounds fun. I also have to remember I am not like a lot of women. Like, I'm okay with casual sex.

SPEAKER_00 31:32

If someone says, Oh, I'm actually looking for something serious, you kindly take the rejection and say, I completely understand. That's why I wanted to share just in case we're not on the same page. That's a part of it. Yeah, you are opening yourself up more to rejection, but that is okay. You know, then that is okay. That means you are not actually aligned and you're not coercing them or convincing them to do something under false pretenses that this might be something more. There are ways to be honest about it without it being, hey, I only want casual sex from you and don't plan to see you again. Figuring out what works for you and how you want to say it is important.

SPEAKER_01 32:04

I do think though, as a woman, like it's attractive when you know a guy is desiring you, but he's also being honest with you.

SPEAKER_00 32:10

Absolutely.

SPEAKER_01 32:12

And if a woman responds badly to that, it really lands in her lap. In my opinion, like it just means you're not on the same page. Right.

SPEAKER_00 32:22

It just means they're looking for something serious. And I understand so many of my female friends who are on apps who are just like, everyone wants something casual. And because of that, they're extremely frustrated when they're looking for something more serious, when they say they're looking for something more serious, and then after having sex or the sex the second time, they say, Oh no, I'm looking for something casual. So they get very, even though they're almost now overcorrecting a little bit, where it's like if someone is upfront about that, that is actually what you want. That allows you to say no. That allows you to be like, we are not on the same page, I don't want to do this. I don't think that makes that dude an asshole. I don't think it warrants a negative response, but I just know from past frustrations and from seeking this that they often can get upset. So if you can do yourself the favor and be like, no, I'm glad he told me, so that way I did not go about this and get my heart broken. I'm a little bit disappointed by this. But yeah, I much rather know. But yeah, I think it's coming from a place of people who have not been up friends, and because of that, they're just turned off by the idea of potentially casual sex altogether.

Sexy Communication With A Stranger

SPEAKER_01 33:30

Right, right. So now you've been honest and you've told them, and you're both like, let's go do it. So we're going back to the bedroom or wherever we're going. What are some of the things that make a one night stand really good? Especially like you and I both know we're given advice all the time. Communication or sex is key to good sex. But what does communication even look like when you're with a stranger and you know it's only one night and you want to get something really great out of it?

SPEAKER_00 34:04

It's I I think sometimes people assume that communication when sex like kind of cults everything, where it's like you get up to the bedroom and you're you're taking out, you finish taking up your clothes, and then you sit down as things are about to get a hot heaven, you're like, so tell me what your boundaries are, tell me what you like when you do this. And that can can completely ruin the mood and stop the momentum. Still, I think it's important to somehow convey these things without losing the momentum. As I'm getting naked and slowly stripping down, what really turns me on is when you do X, Y, and or I really get turned on when I do XY and this. I like having my face smothered. Can you ride me with your ass? Something like that. And it's not this huge conversation, you're just expressing what it is you like, giving the other person an opportunity to do that. I'll do that. I'll be like, is there anything that turns you on? And then do the things that turn each other on. And it and almost put it in a way where frame it as these are the things that let's say you like choking, but obviously you should know how to go about choking safely. It is potentially dangerous, it is intimate. People go about it wrong. And I don't necessarily want to be like right before let's say I'm about to jump like, hey, do you like being choked? And I have done that. I absolutely have done that because definitely don't want to choke someone who doesn't want to. But I think if you do it more in the beginning, as you're getting undressed, I get really turned on by choking. That's something you're into. And just you say this succinctly. This doesn't need to be a huge conversation. You know what they like, you know what they don't like, and then you act accordingly.

SPEAKER_01 35:44

And you can make it part of your sex talk, right? Do you like it when you're around? Do you like to be bossed around? Because I feel like I'm a little bossy tonight. Can I tell you?

SPEAKER_02 35:53

I love that.

SPEAKER_01 35:53

You know, that kind of thing. And then you just get into asking them the questions and telling them to do it. Like asking them and like when you get the confirmation, you can drive that, especially if you're in your dummy dommy energy. Yeah. I think it's a lot easier for me when I'm in that energy. But you can do it from whatever framework you're feeling like you want to for the night, because you may go out for a and I assume you've experienced this where it's like on one night, you're like, I really have the need to have XYZ happen, right? So now you're looking for a one night stand and to have a specific urge met. So if you want to have those things met, then you know you can keep them amended. You go in the room you guys are making out and you say, Oh, would you like to see me on my knees right now? That kind of thing.

SPEAKER_00 36:39

That's one of the beautiful things about grinder is truly you have a tab of kinks. So or not tab, sorry, they like subgroups, so you can put the kinks. And so I, if I'm in the mood to be a sub and get throat flack or bottom or whatever, I just say that before they come over. And this level of direct communication about your desires and kinks is so expected and normalized through grinder and gay culture. So if I have a specific kink that I want to fill out, then I literally just go and ask for it. So then also by the time he comes over, I go to his place. We actually don't need to talk anymore. We already discuss what it is that we want to do before meeting up. We found that we are perfectly aligned, and then and then you just get to go and do it. So the beauty of that. So you can communicate your desires and kinks earlier on the app so you don't have to necessarily break momentum long person.

SPEAKER_01 37:33

So that would be the plus of apps and texting in advance. But that brings me to this that I think a lot of us have run into. Like, I've been on an app, I've been texting, it's hot and sexy. We've got this chemistry. We seem to be aligned. We talked about what I wanted, and you were into it, and what you were into, and then we meet in person, we're gonna have that hot experience. And somehow you're not bringing what you brought through text. Does that happen? Have you had that? And so suddenly you're like, this is not what I expected. And we even talk about it in advance.

SPEAKER_00 38:08

I call those fake DOMs. I think a lot of the time the fantasy of DOMing turns them on, the idea of being in control, whatever it is. So they're saying I want to do all these disgusting things to you or these intense things to you. And you're like, Yeah, then that's what I want. Thank you. I want someone who can do this. And then they come over and they're very tepid. And you're like, wait a minute, like you're all barking, no bite here. What happened? And and the truth of the matter is sometimes that happens, and it's and that's not gonna lead to a great like at the end of the day, going home with someone that you don't know super well or having sex with someone for the first time, like it is hit or miss, you know, that you can do everything right, you can convey what your desires are, you can be kind, you can be compassionate, you can be 10 million things, but uh just don't connect. They were, yeah, the idea of doing something was hotter than actually being able to do it themselves. And so not every single one-night stand is going to be mind-blowing, even if you do everything right at the end of the day, it takes two to tango here.

SPEAKER_01 39:14

Yeah, and I think here's what I would say for women who pick someone on an app, and it may be different. And I think I feel like on Grindr, and I have not been on it, it is not a place for me. But it does. Not quite, no. No, there's I mean, the people that are on Grindr, like there's a lot more experience, and the people there know what they're doing and how they're gonna show up for the most part. But I feel like when women are using apps for one night stands, I think a lot of ladies will agree that again, the energy that we get through text and then we show up to can be very, very different. I would suggest if you're going to have a a one-night stand from someone with from an app, women and men alike, and again, more cis heterosexual, meet for a drink ahead of time, see if you're kicking off that sexy energy in person before you go back to the bedroom and give it a go. Because if you meet in person and somehow what was happening in text has fallen completely flat the minute you're together, it you don't want to have to get drunk to go back.

SPEAKER_00 40:24

You don't know, you definitely don't want to do that. And I think there's something to be said about hey, if you have a good connection with someone via meeting someone online or amps, ask for a meetup sooner than later. Because sometimes you end up texting or going back and forth for three weeks, for six weeks, for three months, and then you are so excited about this and you meet the person and you're like, but within 30 seconds, you're like, shit, then this is this this is not a vibe, and then it's really frustrating. You know what I mean? Where you're like, shit, I invested all this time, especially if you're meeting someone for the first time. I like to do it potentially closer to home. But if I so that way, if I I don't feel like I'm I if you get all dressed up and I spend 15 minutes going from Brooklyn to the Upper East Side, and then it sucks after 30 minutes and I go home, it feels like a wasted night. If you're able to do it someplace closer to you but leave, it doesn't feel like an entire wasted night. I also like like maybe this is too much for a casual thing, but if you're meeting on amps or whatever, I haven't met them in person. I don't mind doing a quick FaceTime, just a five-minute check. That that sometimes discourages people, especially if the younger generation that's so used to texting and doesn't like phone calls or FaceTimes or whatever it is, the Gen Z 25 to or 22 to 30, let's say. But it it just that honestly, oh, it could just be a five-minute gut check. Because I feel like you can learn a lot about something for five minutes and then you hang up, and you then you can decide whether you want to meet, or you can send a nice text being like, hey, it was great to meet you. I don't think we're match, wishing you the best, whatever it is, something like that. But I would do that if in particular you've been meeting people off of line that you were excited about that then ended up not matching. Okay, so you've had some experiences that were not ideal. Okay, so this is the best way to remedy it. If you're not running into that issue, then there's no need to do this.

Make The Sex Slow Generous

SPEAKER_01 42:23

Okay, now we're in the bedroom.

unknown 42:25

Sure.

SPEAKER_01 42:26

We're in the bedroom, clothes are coming off. How do we optimize this experience as so it steers at least towards unforgettable, not let's erase that from my memory?

SPEAKER_00 42:37

I think casual sex does not mean fast sex. That does not mean we're racing to have an orgasm. I think you still want to take your time, you still want to have foreplay, you still want to connect and kiss or whatever it is that you like, even though it's a one-night stand, it should be equally about your pleasure and theirs. It's not just about you getting off or about them getting off, it's about both of you having a pleasurable time. I think sometimes, uh, particularly men, more so than women, although this relates to all genders, can go into a casual stand, a casual one-night stand, and they almost don't respect their partner and they're only using them. And don't be that asshole. Like you should still go into this caring about your partner's needs and desires. So we have that. We have the communication. You're able to do what you want to do. It's called casual sex, but don't go into it casually. I still want you to have that same passion and intensity and drive and pleasure and whatever it is that you would have if you were making love to someone you've been dating for a long time, whatever it is.

SPEAKER_01 43:42

I think it's interesting because as we were talking about this, I thought back to, I have had I've had a lot of really incredible one night stands, in particular with men. I've had one night stands with men that we tried to follow up with, and it was nowhere near as good as the one night stand. I'm gonna tell you why. And I think what made it so successful, I think because he and I both thought this is the only night we're gonna be together. We can be our authentic selves because it doesn't fucking matter. I'm not gonna see this dude the next day. And usually what happens in those one night stands is we end up together for hours till four in the morning, like doing all sorts of things because we we think we're free, we're clear and free after, right? I'm not gonna see him, he's not gonna see me. Let's use every moment of this free, judgment-free nobody knows about secret container. And I feel if you can look at a one-night stand as this secret container where you can be yourself and ask for what you want. Because what if she says, Oh, that's freaky, I don't want to do that. Who the fuck cares? You're not gonna see her tomorrow. Who cares? What do you care if they think you're a freak? So what? Right? You get a walk away from it. So why not be your full self and be like, hey, I really want to try this? And and and if they're not into it, or if they're like, oh, I want to do missionary for 15 minutes, you can be like, oh, all right, do and be done, or just opt out. I don't find that's what most people, at least in my experience, do. Most people are like, all right, let's let's get weird and then say goodbye.

SPEAKER_00 45:29

It's and I was trying to say this earlier. That's what I was trying to say about like how there is a freedom, there is a safety, being able to be your authentic self. It's why for me, like vacation sex in particular with also someone else who's on vacation too. So we're both on vacation, we live on different sides of the country. That's when I have the best one night stands because I'm so unabashedly myself. I'm so free, I'm so not afraid. The stakes are a little bit lower in that sense. So I think that absolutely can help contribute to a phenomenal one night stand.

SPEAKER_01 46:09

And remember, the person you are having sex with, you are projecting what you want them to be onto them. They're probably not that. Enjoy that, right? You don't want to know if they're assholes or not in real life, because as long as they aren't in that moment in that one evening, that's all you need. Don't go and ruin it like I've done with the follow up. Just romanticize.

SPEAKER_00 46:34

Enjoy it. Enjoy it for what it is. Look back on it, fondly. And again, I don't want to say if you think you actually do have a real connection and take. And do this, don't forego it. But sometimes it is a little bit of a fantasy because of you not seeing each other again. And when that's the case, just enjoy the fantasy. But at the same time, if you do think, oh, actually, I could see this being more, I don't want to say like immediately dismiss them, but it's hard to decipher. But I think over time with more one night stands, you're able to.

SPEAKER_01 47:04

With practice. You want to optimize it. Our advice is use that opportunity to ask for the things you want and to be authentic and take advantage of the time. Don't ruin it by being late and being like, I'm gonna pump away for 15 minutes and leave. Like all that.

SPEAKER_02 47:22

Yeah, enjoy it.

SPEAKER_01 47:24

Why would you waste it?

SPEAKER_02 47:25

Yeah.

Aftercare And Leaving With Kindness

SPEAKER_01 47:27

So this brings me to now you've had in my ideal one night stand, several hours of all kinds of dirty sex that you've been craving. You've both had your orgasm or or enough pleasure that you are satiated. Let's talk about aftercare and ending and walking away. How do we ideally close that time in a way that feels good to everyone and leaves this beautiful memory and that we can masturbate to for years rather than a bad taste in our mouth that we're trying to brush away?

SPEAKER_00 48:04

It it's so many people do not realize that what you do after sex is going to influence your perception of how good or bad the sex was. You can have the best sex of your life where you fuck for two hours, you come a bajillion times, whatever it is. And if the moment you're done, you come the last time, and uh while you're still catching your breath, he's already putting on his clothing and be like, thanks, bye. It's oh I I feel used. But what what I thought was this intimate, fun, pleasure-filled experience now has me feel like used. So I like the it's it there's a balance where I wouldn't necessarily recommend sleeping over, potentially. I think that could give the wrong idea, unless if you guys are clearly on the same page about casualness. Sometimes what I I convey that something is going to be casual, but because I'm kind afterwards, they then don't listen to what I'm saying and want more. And that's a little frustrating because I don't want to have to be cold afterwards to like convey, hey, I I really only saw this as casual, but I think there is a balance. I think you're able to huddle a little bit afterwards with an intense scene, get them water, don't immediately jump out of bed, and then whatever it is, it might be 15 minutes later, it might be two hours later, whatever it is. I had so much fun. I thank you for this great experience. I got an early morning, I gotta do it. Whatever it is, just somehow excuse yourself in a way where where, yeah, they just don't feel used. But still, yeah, if you overdo it, then you're almost like too nice and too cuddly, it might give the wrong impression that you want more. So it is a fine balance to have, but I can't overstate the importance of being kind after a hookup. It costs nothing. That doesn't mean you're sleeping over and buying them flowers that gives them the wrong idea. But I think you can just express, cuddle with them a little bit, say that was great, express how much you enjoy them, and then go on your merry way.

SPEAKER_01 50:06

I think it's nice if you want to be uh a good gentleman, walk them to their car, especially if you're at at a hotel or something like that. Make sure they get to their car safe and think just be thankful. Thank you so much. This was an amazing night. Take care. Goodbye. That's it. And then I think something that I'm rather bad at that I'm gonna suggest for people is then if you really don't want to throw out the chance of anything else, if they say things like, hey, let's exchange numbers, this or that, that's the time to very nicely say, Hey, I don't want to give you the wrong impression. I had such a great time, but I really and and if someone feels hurt by that, then that then then that's okay. Or if you've been honest all of the way through, and you can say these things kindly.

SPEAKER_00 50:55

It's and this speaks to what we were saying earlier about being honest about your intentions. So if you made it seem like this could be something more, have a intense passionate sex, and so they're under the assumption that yes, it could be something more, and then you rip that rug out from underneath them. No, that was a big concern. So that speaks the importance of being honest about your intentions from the get-go. So then, okay, even though I said this, hey, it's a reminder that you agreed to. I don't want to say it's not like I don't want to make it seem like it's a contract here, but it's no, I I was clear about my intent and my intent still holds, and that therefore it's no longer on you if you hurt their feelings. If you're misleading, if you are not clear with your intentions, then I do believe it is on for hurting their feelings because you misled them. But otherwise, sometimes it's intense. If if you struggle to do it in the moment, which can be hard, there have been times where I just like like also like my brain is mush. We just had sex for two hours, I exchanged numbers, and then when they text me, I'd be like, Hey, I had so much fun. I I really was thinking about this, and I see it as being I'm not looking for anything serious. Thank you for great. Whatever it is. So sometimes if you're struggling to say it in that moment because it's just intense, you just had sex, you feel vulnerable, whenever it is. Okay, it's okay to give a number, and then once you have some space, it's less intense, you're not necessarily doing it in person, you can do it then. I I think that's an okay option, too.

SPEAKER_01 52:24

Well, I think also for women, uh especially if you're alone with a guy and he asks for your number, saying no is hard because it can also be risky. Because rejection, of course, can even if you're like, oh no, he's been such a gentleman all the whole night, you never know what someone's going to do when they're faced with rejection. But definitely at some point, if that first text comes, being honest and being kind. If you want to try it again, go ahead. But I'm just telling you, in my experience, oftentimes the second time does not measure up, especially if the first time has been so dynamite, but you never know. You never know, I guess. Right.

SPEAKER_00 53:00

Yeah, I know you never know. No, and I've had one night stands that have been so great that it's turned into two-year-long relationships. Like I've had great ones where I felt connected. I was like, I'll give it another shot. Why not? And then I there have been times where I thought to give it another shot, and boy, I wish I had. And so you you win some, you lose some.

Three Rules To Remember

SPEAKER_01 53:18

Yeah, yeah, it's always a great adventure. I love adventures, and that's what I love about one night stands and casual sex, is it's like this fun adventure if you do it right. I feel like this has been a great conversation. We have covered every aspect of this from figuring out if something you want to do to prepping for it, how to find it, all the way through to aftercare, folks. This is take away time for someone who's like, all right, all right, I've been listening to this podcast and I want to do it. I want a one-night stand. Just give them three tips before they go. And we've given them a lot, but I want let's give them just some nuggets to head away with.

SPEAKER_00 53:53

I don't think a little bit. I feel like I've said most of my tips here, but let me try to synthesize what I think are the most important of the tips I've given. I yeah, I do believe the initial introspection as to why you are doing this and is are you in a the right place to do this? And how, if this does not go great, how devastated would you be is necessary. So you're really setting yourself up for success. You know what your intentions are. So really thinking about this critically before going into it. But you've made these decisions, you know, you're ready to do it. Okay, we're excited to jump in. I think like also being okay with rejection. I we didn't necessarily need to talk about that, but if you go to a bar, you're putting yourself out on grinder on whatever it is, and someone's not into you, that's okay. That doesn't mean you give up. I mean, you give up with them. That doesn't mean you give up generally, it doesn't mean you are unlovable. It doesn't mean no one will want to sleep with you. It means that that you were not the same page with that person, that person wasn't feeling it. So rejection is a lifelong struggle that so many of us struggle with. You know what I mean? And and the one thing I'll say about rejection, it is a muscle that you flex, like in terms of getting rejected and how you respond to it. The first few times you get rejected, you're somewhat devastated. And then you almost need more data points where it's like, now I've gotten rejected, and I've also know that people love me and want to sleep with me. I've also had very positive experience where I haven't been rejected. But sometimes, especially early on, and you're flirting, if you're not as confident, whatever it is, you might get rejected more, and you don't almost have those data points that share. I think no, no, I I know this is just one person. So really not letting rejection discourage you moving forward and not letting it be devastating. And then third, yeah, I I think what what's going to make for a good one night stand is communicating what it is you want, especially if you're not gonna see this person again to what we're saying in that. This is your time to be as honest about your desires as humanly possible. You really do have very little to lose.

Where To Follow Zachary Zane

SPEAKER_01 55:57

Yep, there you go. And I love that you brought up rejection. Do not put a lot of weight into rejection from a stranger, right? Why would you care if you don't know who they are, right? Exactly. I love that. That was a good, I'm glad you caught that because we hadn't talked about that. You guys are set. Go and have all the one night stands now. I I am and I'm enjoying it. Um yeah, we're excited about it. Zach, can you tell everybody where they can find you so they can follow you for more advice and information and and keep up with everything you're doing?

SPEAKER_00 56:31

Sure. So Zachary Zayn underscores my Instagram. I'm very active on there. I have a sub stack, which is also called Boy Slat, which is the name of my book. You Google Boy Slat one word, because actually, when I was writing my book, we learned that if you did two words, it's considered a bad word. So it's gonna be tinted on searches. So if you had to do one word to do this, but that is a great way to read my essays. It's a combination of nonfiction and fiction erotica, along with thought pieces, interviews, interviews, anything about sex, dating, relationships. So definitely check out myself back. The last thing I'll say, especially is to read my book, Boy Sled and Memoir Manifesto. The book really is about how to overcome sexual shame, how I went from a place of being just run and so much guilt about seeking pleasure and wanting to date people, wanting to having sex, embracing my case and non-monogamy, and moving to this place of just being empowered and shame-free. So if you struggle with any aspects of sexual shame, I uh heavily recommend you read this book. So those are I'd say the three things where you can see my writing and see what I'm all about and stay in touch. Yeah.

SPEAKER_01 57:34

Thank you so much for joining us today, Zachary. And for my listeners, casual sex is an awesome opportunity for exploration to figure out what you really want, who you want to be with, try new things. If you do it ethically. And we have given you a roadmap.

SPEAKER_02 57:53

Yes, we have.

Listener Questions And Closing

SPEAKER_01 57:56

Have at it and you know that I want to know how it goes. If you have questions or comments, you can do that by going to my YouTube channel at TalkSexwithanet. You can drop your questions and comments and thoughts under the video for this episode. If you're an audio listener, head over to my YouTube channel or email me at Annette at talksexwithanette.com and give me your thoughts, your questions, and your comments. I had stories. Stories. I love the stories. Thank you for joining me today. I really appreciate it.

SPEAKER_00 58:27

Yeah, thank you for having me. This was a lot of fun.

SPEAKER_01 58:29

It was tons of fun. All right, until next time, I'll see y'all in the locker room. Cheers.

SPEAKER_00 58:36

Cheers.