Flirting Masterclass: How to Approach, Connect, & Seal the Deal in Any Dating Situation

Have you ever gone home without getting any action from a house party?

Left a dinner date and not know that the couple was interested in maybe something more fun.

Looked at your watch at 2 a.m. and realized nothing was going to happen to me.

Closing the deal is hard, but we are going to give you some tips on how to make it better.

First, let’s start with some basics. What is closing the deal? Let’s be really clear.

( Laughter ) Getting that sexy couple to the bedroom?

Exactly. Exactly.

We’ve heard people talk about this all the time. The reason why we’re doing this is an episode is…

I think it was actually at HEDO when we were there. We had a… just one year a couple friends of ours who would come up to us and say,

“Does everybody have a hard time with transitioning, closing the deal, getting the couple to the bedroom?” Yes. And… Most. Yeah, the answer is everybody has that trick. Yeah. Most people aren’t a salesperson, right? It’s… most people aren’t doing that on a daily basis. Right. Which… well, especially asking another couple to have sex with them, which is even more unusual.

Yeah, and you figure a lot of the couples who are in the lifestyle have been married for 10, 20, 30 years.

They’ve got a lot of history together, and the last time they did… Oh. …was 10, 20, 30 years ago. They don’t even know how to pick people up anymore. Yeah, those muscles are atrophied, right? We had to learn how to date again. We did, and we’d only been together for a year. And I had been dating, and you had been dating, and it was still not easy. And

I think it is a little different with couples picking up other couples. Yeah. Like, there’s four people that you’re trying to coordinate. It’s not just you and your entangled recipient of all the attention. Right, yeah.

How does consent and communication factor into this? I think it’s pretty important, because you’re really laying down what that other couple is interested in as the flirtation and the seduction kind of moves forward. But I think this is true not only for swingers, but for singles, too, and dating. Really having an upfront understanding of what everybody’s in the mood for, what everybody’s game for. And we’ll get into consent later on in the conversation, because there’s a key point in which you start really talking about consent. But we always like to mention consent, because it’s kind of an afterthought in a lot of places. Yeah, it’s frequently overlooked. Real true consent. Right. So, you’re preparing yourself to be yourself.

And practice your approaches.

Practice builds confidence. We practiced when we were doing so, and we gave ourselves goals for an evening. And we knew we probably wouldn’t be lucky that night. We decided, let’s talk to just one couple. And then it was, let’s talk to three couples. And it was really just getting that muscle, using that muscle, using that over and over again, builds confidence. It’s the whole fake it till you make it. Or practicing your speeches before, you know, in a mirror before you give it. Yeah, and there’s a level of being mentally prepared for what you’re going to set out to do. Being mentally prepared to actually walk up to someone who maybe you haven’t met before. This is the first time you’re talking to them. Maybe you’ve seen them before, but you’ve never approached them.

Really, it’s that visualization process that a lot of sports people go through in terms of seeing the goal before you actually do it. And it helps. It really does help to kind of get your brain in the game. Yeah, I agree.

So in addition to mentally preparing ahead of time and kind of having this game plan,

have an idea of how you’re going to present yourself. And so one of the things that comes across with communication, beyond verbal communication, a lot of communication is nonverbal communication. So your body language. Do you look confident? Do you look nervous? Do you look scared?

Those last two are not quite so sexy. But looking confident looks really good.

That’s true.

Yeah.

Yeah. You could feel it. You could see it in that person’s eyes when they come up to you. You’re like, you know, in the pool, they’re like sauntering over to you and you’re like, oh, oh, the look, the look before they even get to you is like, oh, somebody’s going over.

And one of the keys I think we also want to talk about is don’t be in a hurry to talk. I mean, obviously you have to introduce yourself. But during the conversation, listen, be an active listener. Hear what they have to say. Be interested in what they have to say. And that’ll help pull them into the conversation. If you’re doing all the talking, they’re more of a passenger on this little adventure. And they don’t have anything to contribute. Yeah. Don’t be a narcissist, please. It won’t work well.

And lastly, for the preparation, good hygiene and grooming. Yeah.

And it all has to come down to your presentation. So if you’re dressed nice and you’re confident coming up to another couple, they’re going to be impressed. Remember, this is their first impression of you. So look good. Right. So if you’re not approaching another couple in person, online is a little bit different. And so I mean, how do people do that? Is it just a matter of, hey, let’s grab a drink or let’s go get dinner? Yeah, a lot of times we’ve got some specific examples in here in terms of what you can say. And I can throw a couple out. But the key with online communication is because you can’t walk up to them and you can’t present yourself. Right. So you’re one, you should have a nice profile with some pictures so that when they get the message from you, they can go look at you and your partner and see what you look like. See if they’re interested. Hopefully they’re current. Hopefully they’re current images. We’ve done lots of episodes on having good profiles and having a good profile is really important, especially for those people who are maybe browsing for someone in their area. Yeah. They may come to you and then they’ll have to do the whole approach thing. Right.

But the big thing would be when you reach out to somebody online, what are you interested in from that? Did you just want to start the conversation? Do you want to go on a drink date? Maybe you want to find out a little bit more about them beforehand. But any of those things is good. You’re still starting a conversation with them. So an icebreaker compliment would go something like this.

Hi, we just wanted to say we loved your energy tonight.

You too look like you’re having a great time. Mind if we join you for a drink.

Why this works. Well, one, it’s friendly.

Two, it’s not aggressive. And three, it opens the door for further conversation. It’s not a yes or no answer.

Well, the last part kind of is mind if we’re but who’s really going to go, no, you can’t have a drink with us, but they might. They might say, well, we’re waiting for some friends. We already have a prior arrangement that has happened.

But you can follow up with that. So what if someone says no. Well, thank you very much. That was a very nice compliment. But we have already a standing date drink date with another couple. They should be here in like five minutes. Well, you can always say, well, you know, if they don’t show up, we’re right over there at table number three. Come on by and we’d be happy to have a drink with you. Oh, yeah, that works too.

Did you have another approach? Well, maybe set up the drink date for the next night. That also works. Yeah. Would you be interested in a drink date with us on a different night? Yeah.

Most I would say if you’re not getting the vibe, you know how it is. Like sometimes people will give you a vibe and you’re like, okay, yeah, they’re gonna. They’re probably gonna say yes. If they don’t say yes, they may say something like, well, let me confer with my wife and we’ll get back to you. I’m sure we’ll see you guys around the pool.

Sometimes they do. Sometimes they don’t. A lot of times people are having a hard time saying no. Like the people usually just don’t flat out say no.

they’ll say no, thank you. Have you ever said no, thank you? Not that I can recall. I remember you saying no, you will actually say no, thank you with a smile. Yeah, I’m usually very polite. Thank you very much. No, thank you. But maybe it’s not in swinger situations. It’s usually like when a salesman is approaching you in the mall or something. I will walk past them. A lot of times I’m learning big eye kind of things. I’m like, I’m not gonna do that to you. Let’s give you another example. Okay. Another playful opener because I think a lot of times people struggle with what do I say, what do we do when we walk up to them? Yeah. And I think no matter what the most important thing really is to just just be yourself.

Don’t worry so much about trying to impress them or say the right thing. Coming up to them in the first place is actually a compliment. That’s true.

just stepping up is a big first step.

here’s a specific line that you can also use as an example, you can make variations on this and you can think of other things, maybe something that’s a little bit more natural for you to say.

When people say be yourself, it’s all about being comfortable saying the thing that you are going to present to another couple.

You’re not trying to say things that you wouldn’t normally say. It’s kind of like when you give an alibi for going to a Swinger event.

You keep it close enough to the truth, where it’s believable and you can sell it, you can actually convince the person that you’re telling. Same thing with an approach. Yeah. So here you go.

It’s engaging, invites them to share something personal. And if you have a similar interest, now you have a common bond with that couple. You can talk about your adventures too. And there you go. You started off a whole conversation based off of one small thing in a profile or maybe something that they were wearing. If it happens to be a theme night, you can walk up to somebody and say, I almost wore that costume or I saw that costume online and you are totally pulling it off. Yeah. Yeah. 100%.

that all the time. I mean, it’s an authentic compliment, but we use that all the time when we’re on the bliss cruises because you’re constantly in the elevator with people or walking down the hall, passing people and in their costumes. And it’s very easy to just stop people and give them a compliment and engage them in conversation. Yeah. And in a sense, they pick that outfit to be seen in it. Absolutely. You’re kind of taking them up on that offer. I agree. 100%. As I mentioned earlier, avoid those yes and no questions. For instance, a yes and no question would be what brought you to this event tonight.

That’s better than do you come here often? So the do you come here often is a yes, no.

Okay, kind of wrap that little section up yourself. It fits well with who you are. And so it’s easier to do struggling with it. The other thing is that it builds rapport, it builds trust so that other couple starts to get to know you a little bit. And you’re bonding with them, which is really the most important thing. Watch their body language, their verbal cues to gauge their interest. Are they maintaining eye contact? Are they smiling? Are they laughing? Do they reach out and maybe touch your hand or they’re touching your arm?

Are they flirting with you? So if you’re getting those kinds of go signals, then you can move forward. If you’re not, if you see them kind of arms crossed, closed posture, kind of backing up a little bit, looking around, checking their watch.

If they’re not interested, and you should just move on. Two reasons. You’re saving yourself time, and you’re not wasting their time, which will make them happier.

Oh, yes.

Making the move.

So if you’re getting those positive signals, keep it sexy. Flirt, compliment, touch. I would encourage you to ask first because consent is key.

Practice asking, May I touch you?

May I touch your costume? May I touch your arm? May I touch your hair? People really like that. They feel like you’re really interested in them, that you respect their boundaries. It’s nice. It feels good.

Yeah, I had a woman who was coming up to me in San Antonio, and her opening line to me was, “Your shirt looks so soft. Can I touch it?”

Twist my arm. Yes, you may. Yes, it is soft. And that became our thing all weekend long. You could just come up and touch all of my costumes. She had to see if they were soft, funny, fuzzy, or everything. That’s funny. I didn’t know that, though. That’s very cute. It was an excellent way to kind of reach into that sensitive touching aspect. And flirting. Right. And now she’s flirting, and you’re flirting. And yeah. What about playstyle questions?

Yeah, so if the flirting is moving forward, you’re getting all the positive signals. The body language is open, they’re flirting back, they’re smiling, they’re laughing. Everybody’s touching each other. It’s all good. Now, you can start asking things to kind of move forward. Because it’s one thing to be interested in a couple and flirt with them. It’s another to start thinking about the next with a couple. I know. How many times have you been in a pool, an adult vacation, and you’re kissing, and you’re flirting, and you’re bumping up against them, and you’re touching. Maybe you wrapped your legs around them in the pool, and you’re, you know, making out. But that doesn’t necessarily mean you’re going to wind up in the bedroom. Right. A lot of people are just happy with the flirting, and that’s where it stays. It doesn’t go anywhere.

So to transition, to start to get them to think that you’re interested, start asking them questions about their playstyle. Are they soft swap? Are they full swap? Do they like same bed? Do they like separate bed? Do they play separately? Do they play together? You can start kind of having that conversation, which starts, one, getting their mind tuned to potential fun activities, right? It starts getting their gears turning.

But the other thing is, you find out whether they’re interested in more or not, and what they’re interested in. Maybe their playstyle doesn’t match up with yours. Maybe they’re into like heavy bondage play and impact play, and that’s just not your thing. Well, that’s also a good time to go, “It was fun flirting with you, but we’re going to move on.” Yeah.

Now you’ve got them kind of geared up, and you’re starting to think the same way as them. If there’s a playroom, or a bedroom, wherever you are, you can start to use that as a transition tool. So you could offer, “Hey, we were interested in going and checking out the playrooms. Would you like to join us?” That’s been a really successful line for us, and it’s worked a number of times, and it moves the party forward.

Yes, it works really well. Surprisingly. It’s so simple, but it works very well.

Always be respectful and understanding if that other couple isn’t interested. Consent, once again, is key. And just pull that trigger and ask. I mean, a lot of… It’s the Swinger community, so they’re going to be respectful and nice.

You may experience a slight awkward moment, but it’s fleeting. It disappears, and at least you feel good for putting yourself out there. Yeah. The other thing, much like the other parts where you’re getting the negative body language from them, if you don’t ask them, you won’t get a yes. That’s for sure. But two, if they say no, then that’s also your signal to move on, and that way you’re not going to spend hours and hours hoping that they’ll make a move when they weren’t even interested in the first place. So this asking for process is also important. Like you said, maybe they’re just interested in flirting. Maybe they’re not playful. Maybe they’re not interested in partners. Let’s give them another example. I like this one. The one that starts with

How about, we just got a new comforter on our bed. Would you like to see it? I think someone used that one on us before. They did. They did. I was like, huh? I was like, it didn’t really work on me because I was confused. This was way early on. And I’m like, why would they ask that? That’s weird. And I’m like, oh. It’s because you have to go to the bedroom to see it. And then once we were in the bedroom, I realized, I finally caught up to me.

a brand new mattress. You should check it out. How sweet it is.

And the hot tub and the toy show.

Yeah. Another gateway drug. Yeah. Hot tubs will certainly set people in the right mood.

oh, we didn’t bring suits. Oh, that’s okay. We don’t like suits on our hot tub anyway. It’s bad for the filter.

Yes, exactly. There’s always that comment that gets dropped, which is really kind of fun. Then you’re like, oh, okay. Well, I guess my clothes are coming off. Right.

Another thing that can happen too is if the ladies get together and have a little whispering conversation, maybe go try on lingerie and come back. So if this is a couple that you brought over your house, maybe you guys are the same size or she brought something in anticipation and the ladies kind of step away for a little bit and then come back into the room and boom. They’re in outfits and the guys are going to be ready to go. That’s a very quick way to transition.

Yeah. It’s kind of fun to do that costume change with women friends.

it. You get to have a private conversation. It always takes way longer than it should because we want to have time to chat with each other. We want to have a conversation. We want to make sure we are good and she’s good. I always want to make sure the woman is comfortable and that makes me feel very comfortable and at ease.

that the times that I’ve done it. Initially it used to be awkward, but now I really, really like it.

It’s been fun. I’ve enjoyed it for sure.

The

thing, of course, that we will mention again, we’ve mentioned it now twice. We’re going to mention it a third time, which is when they say yes, start having the conversation about consent.

What what’s on the table? What are they interested in doing? They’ve said yes, you’re transitioning to the playroom.

Right. But don’t ambush them. Don’t be a creeper. Don’t ambush them. Offer them some space to discuss it. Don’t stalk them and make sure you discuss with your partner as well.

Because Ed has been known to write checks that he can’t cash.

And usually those are in situations where we’re really, really comfortable. Ed’s vibing and I might be off that night for who knows what reason, right? And then he’s off there and he’s like, okay, we’re we’re headed this way. And I’m like, huh, what? Where are you going? I don’t think so. I do call a party where I was invited to a room after everybody else had been invited.

Oh, the house party with the pool. And you’d say, by the way, we’re all going to the bedroom. Come on.

Where is Ed? Where is Ed? Get over here, Ed.

conversation about closing the deal would be complete without the possibility of handling rejection. Not everybody’s a match. Not every four way connection actually works. A lot of times it works three ways, two ways, but getting all four people or more to match up. It doesn’t always happen. No. So not everyone’s going to say yes, that’s okay. Don’t get mad. Don’t get upset. It’s supposed to be fun. You’re having a good time. You’re flirting with people. It’s an opportunity. It’s not a guarantee. But it’s it is hard to not invest too much. I saw your note here says don’t invest too much, but that’s hard.

It is hard, especially because that hot couple is the one that you’ve been eyeing all night and you really want to connect with them. Yeah. Or you spent all day talking to them and you really got to know them and they became more attractive because you got to know them so well that now you’re like, yeah, this is great. This is going to happen. And then they have totally different idea. Yeah.

is one of the things about kind of transitioning to that point sooner rather than later so that you haven’t invested all the time.

When we were in Costa Rica, there was a very nice couple that we spent a lot of time getting to know. And about two days, three days into it, we found out they weren’t swingers.

Right. They were just swing or adjacent. They just liked having sexy. Oh, yeah. But we love them. We like we love them. Super great. They are like the best. I would travel. We would waste more time with them. Oh, yeah. 100%. They were super sweet. Oh, my gosh.

And once again, I’m going to repeat this because I think it’s important and that’s king off that body language. So read the room, see what they’re doing and pay attention to that. If you’ve been drinking or they’ve been drinking, it’s those things. I was really hard to. Yeah, just going to say that. Just maybe one of the reasons why maybe drink a little bit less when you’re in that mode and trying to close the deal with a couple.

So possible responses you might receive in this scenario is my wife and I are only playing with each other tonight, but we’ll get back to you. Or one of the responses we got in Costa Rica from that couple was we are only for each other. Isn’t that sweet.

And we love that response. It was a very sweet response. It wasn’t really a no. I mean, it was, but it didn’t sound like a no. It just was makes you go. Oh, yeah. And the other one we’ve we’ve heard is, oh, we never play at these events. We’re like,

Oh, okay. Well, thank you. But it left me very confused. Like, well, why are you here?

They’re just for the chips and day. Yeah, but you will have, especially on cruises, you’ll have people who are. Swinger friendly. They don’t swing, but they love the vibe and they love the community. So they they love to just hang out. I mean, we’re sexy people. We do sexy things. We’re loving and caring and open and what’s not to.

What’s not to like.

who don’t buy with you, maybe they’re not attracted to you. Yeah, you’re not there type. Maybe they don’t like long. Yeah.

Where they just don’t get the energy off of you, right? There’s a whole bunch of different reasons why people don’t. Just have, try to have a positive attitude and remember it’s for fun. And you’re a team. Most important. Make sure that you’re safe.

That both of you are comfortable with going on and that you’re on the same page. So frequent check ins with each other. How you feeling? Pretty good. Yeah. Are you interested in this couple? Should we approach them? Yeah, I think we should. They were kind of giving me some signals. No, I got a weird vibe from him.

Make sure that you have the conversation before you even go up to approach because there’s nothing like getting up to them and your partner looking over at your room. Why? I really like when you say that like we’re a team. There have been times where I will get disappointed or I will get disappointed.

I really like when you say that like we’re a team. There have been times where I will get disappointed

rather I’ll feel guilty that I’m putting on the brakes because I’m just not feeling it and I don’t really know why. And you’re like, no worries. We’re a team. Don’t worry about it. We’re a team. This is a team activity. So if you’re not feeling it, then we’re not doing it. And that always makes me feel great. Yeah. And you know, every night doesn’t have to end like that. Yeah. There’s always another night and you know what? Maybe you’re just not feeling in the mood that night and you just want to hang out and socialize. Maybe you’re just there to catch up with some friends. Yeah, that’s fine. That’s also good. By the way, we’ve been talking about this approach thing. You can also say no to couples.

Like this has been the one side of approaching couples, but when couples approach you, it’s okay to say no, but

Be empathetic. And you can tell them we’re flattered. We’re flattered that you came up to us. We’re flattered that you thought we were attractive or that you were interested in us.

But, and then insert your own reason for why you’re not interested. And if you just go, we’re not feeling it tonight or we’re not tonight. And that’s actually an easy way to kind of put people off a little bit. Yeah. I’m not feeling it tonight. It does open the possibility for them to come back to you. Right. So correct. Yeah. I know a lot of people use that, but like you said, it does keep that door open. So if you really aren’t interested and you put them off, they will come back. Yeah. And like I said, them rejecting you, you rejecting them, you’re also saving them time. They’re not going to stand around and talk to you and try and invest more of their evening convincing you to come to the bedroom with them when you’re not interested. You’re just going to move on. We, we even had a couple say to us, this was at one of the local resorts that we go to during a festival. They said, we were hanging out with them. They were having a lot of great conversations and they, at one point he said, hey, just want to let you know we, we never, well, they said we never played these events, but this, this was a different kind of an event.

And sort of yes and no, it was Swinger adjacent and they were swingers, but they said, we’re love hanging out with you. We’re loving this conversation. Just let you know that we don’t, we don’t play at these events. So in case you were, you were leading that, that direction. I just wanted to put it out there, but you’re more than happy to have breakfast with us and come out and hang out, hang with us at any point. But I just didn’t want to you to feel like we were leading you on in any way. And we were like, oh my gosh. Oh wow. Thanks. Thanks for your honesty. And that gave us the power to decide. Okay. They’re, they’re never going to play with us while we’re here for these next several days. So we can either choose to spend more time with them or choose to go hunting somewhere else. Cause the knowledge is power gives people the power to choose. Yeah. And we ended up hanging out with them some more cause they were really fabulous people.

Yeah. So in conclusion, be yourself. Practice ahead of time. Yes. And have a game plan beforehand and don’t worry about rejection. It’s going to happen, but it’s also going to work and you just got to find the right couple that vibes with you and has that positive feel when you interact with them. I would even say, say, for example, you’re at a pool and you and your significant other on the same page, just, just do a little pow wow. Just float to the other side of the pool and go, okay.

Let’s ask them. Okay. What are we going to say and team up with your, with your partner. Get, get the sentence together, practice it with each other real quick. It only takes five minutes or less and then be lying it over to them in the pool and then just do it. That’s what we’ve done. Rely on each other, lift each other up. You can do it. We believe in you.

If you’ve had any approaches that have worked really well for you, please comment them at the bottom of this and let us know and share with the rest of the community so that they can learn from your success. We’ve all got a different tape on things and it’s always fun to learn new tricks when approaching and trying to close the deal.

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