That Other Lifestyle Podcast — Bad Dates artwork

That Other Lifestyle Podcast · Jayson Lee

Bad Dates

· 30:27

Show notes

Host Jason shares laughable and cringe-worthy stories of bad dates from the lifestyle scene, from awkward dinner conversations and red flags to dealing with flaky or arrogant couples. He offers practical tips on what to watch for, how to exit a bad date, and why these misadventures can become campfire stories.   My links: www.thatotherlifestyle.com https://benable.com/ThatOtherLifestyle Single Men's Guide to the Lifestyle Course Risque Lifestyle Parties SDC.com STDHero.com Hellowisp.com

Transcript


Speaker1: Good morning, good afternoon, good evening. Wherever you are, I hope you have blue skies. Welcome to That Other Lifestyle Podcast. I'm your host, Jason. Leave vanilla behind as you reminisce on bad dates. This podcast is for adults only. We'll be diving into adult and sexual topics with plenty of colorful language. I'm going to cuss a lot, so it is not safe for work. If you are under 18, please stop listening. This show is all about exploring the lifestyle and ethical non-monogamy and its open to everyone, no matter your background, gender identity, expression, or your personal truth. While I do my best to use inclusive language, you might hear terms like husband, wife, or partner for simplicity's sake. This show is for everyone, though. Lifestyle, vanilla, or just the curious. Please pardon my voice this week. For some reason today, when I decide to record, my allergies decide to act up. All right, need to share a secret with you. I cannot listen to Linkin Park, that band that made that song from the first Transformers movie. They're still around, making music for But I cannot listen to them. Anytime they come on the radio, that's a big nope from me. I have to turn the channel. What could have happened, do you think, that could completely turn me off to a band? And it's no offense to any fans of the band. If you like them, you like them. The reason is a bad date. Sitting across from a man that was a living embodiment of mayonnaise. Pale, bland, spreadable. Watching him desperately throw anything and everything at my wife to elicit some interest from her while his wife emasculated. him, this gentleman turned to me and asked me if I liked Linkin Park. I told him I have no strong opinion on the band either way. Not my gym workout playlist, so I'm neutral. I prefer much harder, heavier music, honestly. Long live rock and roll. He said that love of Linkin Park was a deal-breaker for any further connection between us. I know he was kidding, laughed it off. Then his wife chimed in that he only listens to dad rock and no one else likes his taste in music. a frame and bashful folded in further into himself into his own body like a chastised turtle my wife gave me a look that look of what the fuck did you do jason and why are we still here i may have looked back and smiled i wanted to ride this glorious train wreck we were sitting on the patio of a restaurant in hard metal chairs that made my ass hurt my wife and i made dinner plans with this couple it was a local thing no pressure right we've been texting for a few weeks no red flags that i can remember we were early and then wonder where the hell everyone is because I've been waiting 10 minutes. The couple walked in. She was dressed in a schoolgirl outfit while he was wearing a silk shirt, mostly unbuttoned, exposing his hairless white chest. I could hear my wife's vagina dry out. It was like a reverse sponge. She looked at me and said, what the fuck did you do? Me? I responded. You're on this fucking train with me. We tolerated a lot more. We didn't know the red flags. Dinner went well, though. I did sneak off to the bathroom to double-check their profiles, and that is when I learned. On some of the sites, you can see when a picture was uploaded. Their pictures were seven years old. Seven years old. The conversation was stilted. My wife had zero interest in this man, and I could see it. Purse to lips, distant looks, she kept running her fingers, over the edge of an empty glass. No second round here. Just ready to be done. And we couldn't leave. The wife, she was very bubbly. The kind of bubbly that is only exasperated by alcohol. The kind of bubbly that lets you know in no uncertain terms, this woman is interested. She caressed my knee under the table. She leaned forward to press her words into my body. And all I could wonder is, where the fuck did she get a schoolgirl outfit this time of year? It was March. That means she already, She owned that and she picked it out. She chose to wear that. I would say the outfit left little to the imagination, but I really didn't want to imagine any of that anyway. You know how you want to wait for a natural stopping point to end a conversation? Never really got to that point because this man was throwing everything at my wife to impress her. He asked my wife about her job, her super boring job. That was a dead fucking end. An immediate turnoff is to ask my wife about her job. She doesn't enjoy it, so why talk about it? This dude mentioned that he played in a band 15 years ago, so that didn't land. He mentioned the Linkin Park thing, like I said. He asked my wife if she likes sports cars. This perked up my wife's ears for a second until he clarified that he used to own a sports car and they traded it in for a minivan. To which his wife cackled and mentioned how much stuff they could fit in the van and how sad this man was that he had to trade in his sports car. After dinner, because I just wanted to keep riding this train, we migrated to the As we transition, my wife is sending me the death eyes. You know those eyes. They are full of venom and blame. I whispered, at least we're going to have a good story, and she made it clear that we are not doing this again, and I smiled. I know, I know. Finally, I had to call it. In the middle of a sentence, I don't remember what he was saying. I did the, uh, whelp, time to go thing. They were sad. In consolation, he offered my wife, and I guess me too, to come over to their pool sometimes. And I said, Oh, you have a pool. He said, well, technically it is for the apartment complex, but we're welcome to come over. Of course, we had to be mindful of my wife's bikini choices. I'm skipping over so many details and twists and turns in the interest of time and work count. So yeah, that was one of my worst dates. Had another couple fight. They got into a fight at dinner. It was like hushed arguing. Had another couple, apparently his wife had coached him on the answers to questions, and he kept fucking it up. And you could tell he was fucking up. by the way she was looking at him. And this was like innocent shit like their age. Bad dates. We have all had bad dates. And apologies. You have not had a bad date? Oh, well, just fucking wait. Bad dates are both subjective and they require experience to truly appreciate. Two couples can go out on a date and you'll leave the encounter wondering, who the fuck are these people and how are they allowed in public? A friend can go out with the same couple? Have a blast. It is all subjective to the viewer. the experience are kind of like art. Some people see a scribble, others see a life-changing abstract painting. Granted, there are couples out there, I'm warning you, they're just bad fucking dates. Unsettled, jealous, boring, drunk, lots of options on that bad date bingo card. Maybe today I can share stories from my own collection, give out warnings, and hopefully help you become a better date. When you are new, every date is fun. When we started, we dated a lot more, because we were new, we needed to meet people, right? We were excited to meet new couples, and yeah, we just said, okay, sure, let's go to dinner. In hindsight, though, some of those dates were really fucking bad. We didn't have perspective on what makes a good date, so we couldn't say what was bad about a date, just a general sense of unease. You got the ick, the you-don't-stick-your-dick-in-crazy kind of moment. Went on one date one time where the activity of choice, the other dude, wanted to go go-kart racing. This is not my jam. I mean, I, I own a driver's license and I drive a full-size car. But sure, let's go play Mario Kart Midlife Crisis. This dude, I will admit, he smoked me. I don't know if it was my seconds, minutes, it could have been my whole lap. Whatever. It didn't bother me because my self-worth isn't measured by how well I can Tokyo Drift in a lawnmower with a seatbelt. See, my pride is tied to more important things like the fact that my dick works. His not so much. And honestly, in my experience, the more arrogant the guy, the more likely his penis won't be up for the party. We've all been there. For the newbies who may tune in, let's talk about what makes a bad date so we have a good place to start. And I want to share so many stories about bad dates. I gotta reinforce this. You may have a bad date with a couple, and your friends go out with them and have a fantastic time. Subjective. Subjective is the encounter, the situation, the location, and the conversation. But there are generally some notes here that I think we can all agree on. First big huge turnoff. conversation. Went out on a date one time a couple years ago. This man, he talked for two solid hours. I am not exaggerating. And I'm a dude who talks a fuck ton, right? It was too much for me. My wife and I barely got a word. And he talked about his life history, his family, his job, his shoes. Bless his little heart. He did not want a single second of silence. The only time his wife talked to us is when he went to the bathroom. I have to give people grace. this and other situations because yeah doing a date can be anxiety inducing if you were new or don't date much or maybe the date is an intimidating couple i get it nerves are there going getting into dating and the lifestyle it's a whole brand new animal especially if you have not been on a date in 20 years and okay wait please don't take all this to mean that my wife and i are perfect dates either we are certainly the fuck not positive someone out there is sharing a story about us and with their friends about how much we sucked on a particular occasion. Positive at some point in our LS journey, another couple has faked their kid being sick to bail on us. Positive at some point in our lifestyle journey, two couples doing a big group date have ditched us to go have their own fun. It sucks. I'm not coming from a place of being an expert. This is just the voice of experience. Conversations should flow. Conversations are a four-way dynamic, just like sex. Here's a tip. If a person is bad at conversation, they will probably be bad at sex. If the dude or the woman, for that matter, only wants to talk about themselves and, you know, nerves are not really the reason, some people, look, just fucking want to dominate the conversation. Yeah, I can almost guarantee it's going to be bad sex. Or, flip side, the stone silent couple, like they're waiting at a doctor's office and they don't want you to speak. Don't ruin the moment. To avoid this, have topics to talk about, so do this. Talk to Your Spouse Tonight and come up with a list of things you are interested in or passionate about that are not your children, job, or medical history. I offer a Conversation God, Take Your Shot, Conversation God, available on my website, thatofthelifestyle.com, which can help. Sign up with an email and you get a free copy. And don't worry, I don't send out emails. The Bragger Couple. They brag about how much money they have, how popular they are by extension, how they can make you more popular by hanging out with them. They like to flex their wealth like it makes them more attractive. It does not. And from personal experience, I can tell you that that couple that wants to help make you more popular, introduce you to more people, they fucking won't. They are bragging to get into your pants. Tell you another story. We met a couple years ago. and they constantly bragged about being close to another popular couple and how popular they were and that they had this in they had this exclusive in to this exclusive hotel takeover those fuckers ghosted us and we ended up going to the exclusive hotel takeover they kept going on and on about about a year later nobody knew who the hell they were so take that i've said it before you can tell a lot about whether these people are worth your time based on how they treat each other how the Spouses treat each other. Going back to my date story at the start, at one point during dinner, the other husband asked my wife if she liked motorcycles. My wife responded that she was neutral. They're fine. Noticing a pattern here, right? This poor bastard could not make a connection. Well, he shared that he wanted to get a motorcycle, didn't have one. And his wife chimed in that he could not. She would not allow him to get a motorcycle because she would not pay the insurance for it. That was very emasculating. I felt kind of bad. for the poor bastard in front of us. It was awkward. And I love awkward, so I am here for it. Another one is the heavy drinker. I get it, a first day can be intense, especially for newbies, but come on, don't drink so fucking much. Keep it under control. If you need a couple of shots of whiskey in order to function or some sort of gummy for social anxiety, hey man, it might be time to calm the fuck down. I've seen a man finish an entire bottle of wine at dinner and then get a margarita. Dinner's like maybe an hour, maybe two hours if you're talking. Whole bottle. and then some. I sat there in disbelief. I am not a heavy drinker, so this was impressive to me. Ever gone on a date with people that were not swingers? We have. A guy messaged me through a dating site and he wanted to go out one night. They were honest, said they were interested in the lifestyle, so we figured, okay, fuck it. Sure, this could be an opportunity to mentor. I don't do that anymore. And introduced them to the lifestyle, which was a wonderful thought we had. We thought we were doing good. The husband sprung a swinger date on her. They got home from work. He told her to get dressed up and didn't share any details. Just said, we're going to go meet some people for dinner. Husband and wife show up. Husband has the biggest shit-eating grin on his face, and his wife looks very confused. They sit down, and he declares to her that, hey, these are swingers. Thanks for introducing us so nicely, dude. he didn't tell her they were having dinner with heathens my wife the wonderful angel that she is caught this she turned to the wife and the most reassuring voice said nothing is happening we're not doing anything physical this is just dinner i could tell the other wife was having a silent freak out that her husband dragged her to dinner to fulfill some fucked up fantasy he had that she was not ready for then the husband starts playing ask a swinger Ever happened to you? Happens to me all the fucking times since we're very open about this. Someone finds out what we do for fun, and then the questions start. He did have some knowledge about this, which I respect, and this is where I got one of my favorite sayings, by the way. This dude asked me about getting his wife an anklet or a black ring, which keep in mind at this point, he was actually running with this idea. I think he just wanted validation to do it. They had discussed having a threesome or adding in a new dick a few times, and he just got really excited without talking to her. So excited, he made a profile without her knowing. Set up a date, and now this poor woman is trying to process all of this. Anyway, he asked about jewelry. My wife will wear a very small demure pineapple, sometimes, but nothing that screams, hey, we're swingers and looking for fun. And I asked him, if he saw a woman wearing an anklent on the other side of the bar, would he approach her? Did he think that piece of jewelry was enough? And for clarification, I know people who do wear the anklents and black rings. I couldn't tell you if I've ever seen one in a public space because I don't look for them we're not out on a Friday night at a random bar looking for connections I have the internet so I told him honestly dude no piece of jewelry will give you any actionable intelligence about anyone's sex life and I love that phrase and I use it often he kept asking questions though he asked how often we fucked around with other people and I told him I can't answer that that's kind of considered a faux pas And at that point in time, my wife and I had a special lady friend. Her husband was traveling a lot, so she would hang out with us. And he asked if our relationship was transactional. As in, we were keeping track of how often we hang out with our special lady friend, so her husband, when he gets home, would be entitled to have the same equal number of times of sex with my wife. Like, fuck no, dude. It was awkward. Not sure what happened to them. Afterwards, he did send me a few spicy pics of his wife. I was like, Huh. Okay, man. Does your wife know that you were sharing this, and is she cool with that? He stopped texting after that. Finally, you need to ask yourself, can these motherfuckers behave in public when you are proposing a dinner? I don't know why. There's a contingent of lifestyle people out there who cannot fucking behave in public. They think they're going on a swinger date, and they now have permission to act as wild and stupid as possible. Look, no one at the restaurant wants to see us play grab-a-dick under a table. you should have if you want to fly under the radar. Are these crazy motherfuckers about to show off tonight? Can we contain this energy? Or conversely, should we run with this energy? Are you ready to party in paradise? Risqué Lifestyle Parties presents Pulsify 2025 at the Island Resort on the sparkling waters of the Gulf Coast in Fort Walton Beach, Florida. September 26th through the 28th, 2025. 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Compare the prices and see for yourself. STD Eros kits are shipped to your home in discreet packaging, utilising painless blood sample collection. Be safe out there. Be a hero of your own story. No discussion of bad dates is complete without talking about red flags. Yeah, there's a topic to watch out for. Leading up to the date itself, what are the red flags that this is going to fucking suck? These flags may be red, right? Maybe not. Could be yellow. Could be green. Subjective. Let's go with the list of stuff because that list is so much easier for me to write. And I preface all of this by saying, look, life happens, okay? Kids get sick, babysitters fall through, cars break down, shit happens. But what matters is how the other couple, the ones who are currently in that shitstorm, handle it. Do they cancel the day at the last minute, which is fucking rude, okay? But it happens. It's happened to me and my wife. Don't take it personally. What happens after matters more? Do they reschedule? Do they apologize? Rescheduling goes a long way to allaying any concerns about whether or not this couple is worth your time. Flaky couples though, ones who don't want to commit to a date, fucking sucks. Here's a hard fact about the lifestyle. Hard truth and I will fight anyone who wants to argue. Some people, not all people, won't commit to a date until they know all their options. I said it. Mic drop. Let's go meet in the parking lot if you don't like it. You may ask to hang out on a Monday and they won't give you a straight answer until Saturday afternoon. Now they could be looking at their schedules and trying to make it work. That's possible. Or they could be right shitheads and they're weighing out their options, waiting to see if anything else better comes along. People may gather all of their week on invites into a fishbowl and pull one out at random or do a deep forensic analysis into which opportunity has the greatest potential for fuckery. Why go on a date when there's a party? I've heard horror stories of people ghosting dates who set up a time and a place and poof them sons of the bitches don't show up and then they stop communicating so yeah maybe they got cold feet maybe something happened on the car right over they suddenly decided we don't want to fucking do this I would personally love to be in the car on the ride to the restaurant when a couple decides nope we need to quit the lifestyle right now I love awkward what's funny talking about flaking ghosting I see it on profiles this really assertive statement that gets copied and pasted around. The couple will express how they never flake or ghost and expect the same from others, that they go through all the trouble and expense of securing childcare and time, and they demand that couples show up for dates. Yeah, you fucking tell them. You tell all these people looking at ass and titties on this site your commitment to showing up. Does this help? I haven't a fucking clue. It's not on ours. You can demand respect all you want on a dating profile. It doesn't mean you're going to get it. A few more flags. Arrogance. I need to add this one since we recently We asked a couple of me for drinks via texting, and the gentleman responded with, Get this. Are you ready? Are you ready? Pause for dramatic effect. He said, Get in line. That's it. He told us to get in line. I could hear his asshole pucker up after he sent the text to the ether of the universe. His wife jumped in immediately to smooth it out and say, you know, they have a lot of other commitments and things to juggle. He's like, he didn't mean it that way. He's like, okay, dude, you said it. You live with it. If a couple acts like they're doing you a favor by going on a date, walk the fuck away. I promise that would be a miserable time and you are saving yourself the price of dinner by not fucking around with that. Another red flag, the overly pushy couple. It's one thing if the sexy talk is amicable between everyone and there's a clear expectation leading into a date, but it's another thing when the other party just really wants to fuck you and you're still in the figuring out stage. If a couple asks to go to a second location, Pro Tip here, they want to fuck you. And speaking of testing, go to stthero.com for all your STI testing needs. Use promo code TOL15 for 15% off your order. Now, whether or not you want to fuck them, fuck this couple, that's what you're having the date to find out, right? And look, to be honest, we have had a sexy offer sprung up on us at dinner. We were talking to a couple, we went to dinner, and at the end of it, they said they got a hotel room for the night and were welcome to join them. I love this. There was no pressure. They were super polite about it. They even got up from the table and excused themselves so my wife and I could talk it out. Fucking stellar. Gold star all the way. We then had to stop by a store to get condoms because this is why. This was way before we started carrying our hoe bag. This encounter, actually, is the reason we started carrying a hoe bag all the time. It's never a guarantee anything's going to happen, but I'm going to be ready for it, damn it. Oh, here's another weird one. The couple that is not dressed for the occasion. You are going out to dinner to meet people you potentially could be having sex with. Not dressed for the occasion. What I mean by that is either they put zero effort into their appearance, baggy t-shirt and looking like they just rolled out of bed at 6 p.m. on a Friday night, or the couple that is dressed in club outfits just going out to dinner, like neon green fishnet stockings and are But she's hanging out. Yes, the sexy outfits are fantastic for a rave. Not so much a buffalo wild wings, lady. Now, dear listener, what happens if you find yourself on a bad date when the bombs are dropping racist, sexist, misogynistic, mean, or boring bombs? First dates, please always go to a public space. I know that couple made their house sound really fucking cool. They have a foosball table and beanbag chairs and a whole sex room. But come on, be smart here. Yeah, go to public first. After a series of bad dates, my wife and I learned to use code phrases. Innocent things we can drop to a conversation to communicate what we're thinking about without anyone being the wiser, like, oh, don't forget we gotta take the cat to the vet next week. This is a way better method than your wife frantically tapping and then slapping your leg under the table and you're not sure what the fuck she is trying to tell you via Morse code. For couples who have kids, lucky you have the perfect out. You fake a testament, text message and oh no the kid is sick we gotta bounce i know people do this i have heard of people doing this kids get sick a lot finally if you're going to you know worried about this always bring cash in case the date goes really really sideways and you can't wait for the check you throw the cash on the table to cover the meal and you'll walk out you have full power to walk out from a date you don't owe anyone explanation or a reason they started talking weird start talking about conspiracy theories it's time to go fuck being graceful and polite just We talked about what makes a bad date. Red flags to look out for. Things that this tells me this is going to be a shitshow. Here's a question to ponder. If you go on a date with a couple and it is a wild shitshow, they're guilty of multiple infractions I have discussed today, do you say anything? And I don't know the answer. I don't know the right answer. Here's another hard truth. Those shitshow couples, they will tend to wash out of the lifestyle after a few months. Word gets around that they are walking red flags and people don't want to associate with them. Will they ever know that their behavior is a problem? I don't know. To address the behavior, that would require confrontation. And people, are people in the lifestyle more confrontational? Not more so than the rest of the population. I've found people who will speak up right quick and others who won't say a word. Having a difficult conversation about the actions of others, that is a hard one with no firm etiquette. an orgy. I can't tell you how to confront someone. We've had our fair share of bad dates and bad other encounters. Have I addressed them? No, not many times. The rub is if a couple is so bad you never want to interact with them again, why bother engaging again and correcting the behavior? And I know there's a population of people out there who want to help and mentor and foster newbies in the lifestyle. I get that. Good for you. People who naturally want to help others. Help people get better at this. This is noble and good. That's why I started the podcast. This conversation could be very good for couples who habitually do bad dates, or it could go very sour. It could come across as being an asshole because nobody wants to have their behavior corrected. No adult wants that. Everyone believes themselves to be perfect in their own minds. I can't tell you if it's worth it. I can't tell you if you should do it. If you do decide to say something, do it with grace and courtesy. Assume positive intent. I feel grace is a big factor in the subjective nature of bad dates. Like I said earlier, two couples could go on a date with a bad couple I also see correlation between horniness and the acceptance of bad behavior. I said it. It's out there. The horner you are for a couple feeling that connection, the more likely you are to let otherwise rough antics slide. Horniness is a powerful motivator. Thinking with your pecker can get you in trouble or have a lot of fun depending on how you look at it. How to avoid bad dates. I don't think you can. And that's what's wild when I think about it. You don't know until you roll the dice on this. Yeah, the couple can say all the right things during a chat, but until you're in the game, you don't know. And bad dates are going to happen. People won't connect. People may be weird and not in a good way. A woman may slam sake and then decide she needs to pop out her party nipple. I say bad dates should not be avoided. Bad dates, yeah, sure, they suck in the moment. They take up your time and energy and all that, but they also give you legendary fucking stories to share later. They're basically the camp Fire Tales of the Lifestyle. Nothing bonds people faster than trading horror stories like baseball cards. It's like, oh, did you have that couple that fought in the bathroom for an hour? I got the one that fought for half an hour. Good times right there. If you ever accidentally become the star of someone else's horror story, don't sweat it, man. Happens to all of us. Somewhere out there, you're the punchline of a drunken story, and that's just part of the game we play, and you're never going to fucking know. My buddy has the philosophy that he will never know how many stories he is the main character in. I like that. For the newbies panicking out there right now about their dating skills, relax. Nobody's expecting you to be super smooth. Just be yourself, use your words, and most importantly, don't be a dick. Seriously, that's like the lifestyle golden rule. Don't be a dick. If you can manage that, you're already way ahead of half these people. I always appreciate hearing your comments and feedback on episodes or suggestions for topics, so feel free to reach out to me at host at thatotherlifestyle.com. My website is thatotherlifestyle.com. My personal disclaimer, I'm not a medical professional nor a trained and certified educator of any kind in any way. I am a guy with a microphone sharing my personal experiences with you. This podcast is for entertainment purposes only and please join us for the next episode. Testing, STI testing is important. It takes a community to make a difference. Go to stdhero.com and use my promo code TOL15 for 15% off your order. Whatever you may do today, I hope you have a fantastic time doing it. Know that you're appreciated and loved. Have a great day.

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