A quick ‘Thank You’ from Dr. Jess and B (it really is us!) – Every time you shop using our links or the code DRJESSVIP, you’re investing in pleasure, education, and empowerment — and we’re so grateful to have you along for the ride. Thank you again. Your support means a lot to us!

Considering a Threesome? Start Here: Your Inclusive Guide to Pleasure, Consent & Connection

You listened to Part I of our threesome series, and now you’re back for the practical prep. In Part II of our threesome discussion, we share questions and prompts to consider before you have a threesome — for individuals and couples. We also share some of our listeners’ insights on how to prep for a threesome and discuss couples’ privilege. Whether you’re single, partnered, or somewhere in between, use the prompts below to design an experience that feels thoughtful, consensual, and genuinely pleasurable for everyone involved.

(If you missed our conversation with Dr. Justin Lehmiller, circle back for the research on who fantasizes, who follows through, and why the numbers don’t always match.)

When (and IF) you’re onsidering moving from fantasy to action, check out this post on how to prepare for your first sex party and ease your nerves while maximizing pleasure.

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Threesome Preparation Toolkit

Below are three sets of questions. Reflect on them solo, discuss with partners, or copy-paste into a shared doc. The goal is clarity—about desire, boundaries, and after-care.

1. Personal Reflection

Threesomes: Self-Questionnaire 

• Why do you want to have a threesome?
• Where did the idea of a threesome come from? How do you feel about this source?
• What benefits do you expect to derive from a threesome?
• What are the perceived risks/costs?
• With whom would you like to have a threesome? Do you know if they’re open to it?
• How might your relationship with your threesome mates change post-threesome?
• What excites you most about a threesome? What motivates you?
• What concerns you about a threesome? Do you have any hesitations?
• What emotional elements of a threesome have you considered?
• How will you manage potentially challenging emotions should they arise?
• Do you feel comfortable communicating your desires and boundaries? What conditions increase your comfort level with open communication?
• What does your ideal threesome entail? Consider the setting, relationships, involved parties, sex acts, etc..

2. Managing Jealousy, Insecurity & Other Big Feelings

• Am I comfortable admitting to feelings of jealousy, insecurity and distress?
• I tend to feel jealous/insecure/distressed when…
• When I feel jealous/insecure/distressed, it shows up in my body as…(emotional presence)
• When I feel jealous/insecure/distressed, I want to…
• When I feel jealous/insecure/distressed, I can self-soothe by…
• When I feel jealous/insecure/distressed, I’d like you to…
• When I feel jealous/insecure/distressed, I don’t want you to…
• You’ll know when I feel jealous/insecure/distressed when I…Some other cues to look for include…

3. Couples’ Conversation Points

• Whose idea was it? Do you feel any pressure? Have you (in)directly pressured your partner?
• Why do you/we want to have a threesome?
• What do you/we hope to get out of the experience?
• What are my/our concerns about the experience?
• Have we talked about jealousy, insecurity and other potentially challenging emotions we might encounter?
• What would it look like if it goes well?
• What might it look like if something goes awry? How will we communicate and respond?
• What do we value in a third-party? What type of person do we want to connect with?
• Do we want to involve a stranger, an acquaintance, a friend and/or a sex worker?
• Have we considered our couples’ privilege and how we can ensure that all voices are heard and respected?

For exploring how jealousy might manifest, check out these strategies for managing jealousy so you feel more grounded and secure going in.

Threesome-Lite Options (If You’re Curious)

• Erotic dialogue: Describe a threesome scenario to each other in detail.
• Shared porn or erotic literature: Pause and discuss what you’d mimic or modify.
• Blindfold role-play: One partner uses hands, mouth, or toys to imitate “extra” sensations.
• Virtual play: Book a private cam session with a performer—tip generously.
• Observation night: Visit a sex-positive venue and simply watch, then debrief together.

Remember: Imagining or talking through a scenario is legitimate sexual expression. You never have to move beyond fantasy unless everyone involved wants to.

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Rough Transcript:

This is a computer-generated rough transcript, so please excuse any typos. This podcast is an informational conversation and is not a substitute for medical, health or other professional advice, diagnosis or treatment. Always seek the services of an appropriate professional should you have individual questions or concerns.

EPISODE 221: How To Prep For A Threesome

 (00:05):

You’re listening to the Sex with Dr. Jess podcast. Sex and relationship advice you can use tonight.

me.

Brandon (00:16):

Welcome to the Sex With Dr. Jess podcast. I’m your co host Brandon Ware here with my lovely other half, Dr. Jess.

Dr. Jess (00:23):

Hey, and it’s just the two of us here to talk threesomes. This is part 2, to follow up from last week’s episode with Justin Lehmiller and I think this is going to be an interesting discussion. Because we’re going to share two things, one is a set of conversations and reflections to consider before you have a threesome, sort the how to prepare. And also I wanted to share a bunch of your responses on threesomes because I received a gazillion. So I’m just going to read them at random. I’m not cherry picking them. I kinda just picked a whole bunch out totally random because yeah, I’m fascinated by what other people have to say about their experiences or their desires. So I put it out on my instagram and asked folks “who fantasizes about a threesome? Who actually wants to have a threesome?” And so as we said last week the data suggests that many people fantasize about a threesome, but not as many actually do it, and then somewhere in between there are people who want to do it. But on my IG, and we had thousands of answers actually, sixty one percent say they fantasize about having a threesome. Thirty nine percent say they don’t. And then the numbers are pretty much aligned for desire, which is interesting. Fifty nine percent say they want to have a threesome and forty one percent say they don’t know. I thought there would be more of a differentiation between fantasy and desire but for our followers, or at least the people who answered it, was just pretty much aligned. Which is interesting to me.

Brandon (01:46):

I would have thought that the number of people who desired a threesome would have been higher, just because of its prevalence in the media and TV shows. It’s like everyone always thinks that that’s the fantasy.

Dr. Jess (01:57):

Yeah and you know, according to Justin Lehmiller’s research, and research that came before it, you’re absolutely right, it’s within the higher eighty five to eighty nine percent range in terms of desire. I wonder too though if folks who may be engaged with my profile or followers in our community also may be a bit more reflective about what they want. So they’re not just watching porn and saying “oh threesomes”, and I’m not suggesting that there’s anything wrong or basic about wanting a threesome. I’m not suggesting that there’s anything wrong with wanting to have a threesome. I definitely, it’s you know, it’s a fantasy for me. It’s something that we’ve definitely explored together. But I just thought I’d throw that data out there and then I’m going to read through some of your responses. But before I do I definitely want to announce this exciting new sponsor with whom we’re working, and that is Lovehoney. And you’re probably familiar with Lovehoney, because they have been in the business of sexual happiness for almost two decades. And I knew that they were big in the UK, but they’re really becoming a powerhouse in Canada and the States as well. And I know I work with many brands but Lovehoney a bit of a standout for a couple of reasons. First and foremost they recently received a couple of awards from the Queen of England.

Brandon (03:01):

What? The Queen of England’s getting her freak on?

Dr. Jess (03:04):

I guess so, you said it, I didn’t say it. You’re the Brit here. And secondly, they’ve actually been sponsoring my show on TSC all about sex toys. So I’ve become intimately familiar with Lovehoney products. Do you remember when the boxes arrived and the boxes were big enough for me to fit in? That’s how many sex toys we received. Boxes and boxes,

Brandon (03:22):

Copious amounts of sex toys thanks to Lovehoney. It was a little ridiculous.

Dr. Jess (03:28):

I loved it. I had to try them out and and it’s interesting, they seem to carry everything. Like I have never actually seen such a diverse range of products. Everything from kind of high end brand name toys that you’ll be familiar with from my other sponsors, so they carry everything. They also carry like little tiny pocket-sized travel toys with travel locks which is really cool to me, their Ignite line, they have lingerie, and they have their own line of products as well as the only Fifty Shades of Grey licensed product line. And I thought I’d bring up one of those toys, because it’s a bit of a standout in that I haven’t seen a toy like this before. And it is the Greedy Girl Thrusting G Spot Vibe. And I was doing a demo of it on TV the other day. I’m just watching this thing go, is so cool, so it obviously has this bulbous head that curves against the G spot, but it also is, it is almost like a gentle spring, so it also thrusts on the inside and then it has curved clitoral arm for the outside, so it’s kind of got every single possibility.

Brandon (04:32):

So it’s any partners perfect toy, because it removes any sort of additional responsibility to help the one partner get off.

Dr. Jess (04:39):

Like lower the pressure, yeah. And so Lovehoney has a big design team and they have a gazillion reviewers — I keep using that word — working on constantly improving their toys. So many of their toys have all these cool features, whether it’s — I keep going back to the travel locks and travel cases because that’s really relevant to me, since I’m hearing them in my suitcase — but I do highly recommend you check them out and you can check the links in my show notes or just head to lovehoney.ca or lovehoney.com. And you can use code DRJESS10 to save on, I think pretty much everything, which is a good deal because usually when there’s these promos there are many, many exclusions, but this one is across the site, so do check them out Lovehoney. And we want to thank them for their support. And with that, it’s time to dive into threesomes.

Brandon (05:25):

Let’s do it.

Dr. Jess (05:26):

All right, so last week we talked about the data with Justin Lehmiller, and this week I wanna talk about considerations and conversations that make for better threesomes. And one thing that we continuously hear, and I think Justin said this, and I said this, and the research shows, that when you prep for something, it’s almost always better right? In terms of the building of anticipation, the excitement, the pleasure, and I think also just the outcome right? When you’re prepared, it’s not just something you stumble into you know, because you’ve been drinking in a hot tub.

Brandon (05:51):

Yeah the first time I heard somebody talking about preparation was actually Luna Matatas at one of the trade shows. And she was commenting on preparing for kink play, and having discussions with your partner and it wasn’t something that I had really thought about before. But when Luna was explaining it, it made so much sense. You have this open conversation from the beginning, everyone explains what it is they’re hoping to achieve, what they want to get out of it, and more importantly, what are we going to do after the sex or the play is done? Which I, just you think about a threesome and I immediately go to pop culture, people are at a party, people have probably been consuming too much alcohol or whatever and then it happens and then it’s done. But when you think about planning everything and then okay, are you staying for food after, are you spending the night ,are you leaving? What do you want to get out of it? It could make the whole experience so much better.

Dr. Jess (06:44):

Yeah, the afterglow or the after care is so important. And it’s interesting you think about a party. I think about couples unicorn hunting, because that’s who I hear from so often, couples who want to find a third. And the messaging from couples is pretty consistent and also very predictable and fair. I understand that you know when you have something good you want to preserve it and so then you want to prioritize it, but in doing so I think a lot of us, and I think we have been guilty of this in the past, don’t really acknowledge and deal with our own privilege as a couple right? So I think that it’s so easy for a couple of say, “oh we wanna find a third person who will do this and do that.” They have this laundry list of wants and demands, but they aren’t really always thinking about the third person, so I think that’s a really important piece that a threesome isn’t just about adding third into your existing partnership or play.

It involves creating a whole new three way dynamic and connection, and this doesn’t mean that you all have to play or interact in the same way or it needs to be perfectly equal, but you want to attend to the feelings and needs and boundaries and desires of all parties. And having that laundry list of wants and demands from couples is a complaint that we hear from unicorns. And by the way, a unicorn is a single person who will hook up with a couple. Oftentimes it’s as cis woman, oftentimes they’re expected to be bisexual. Of course that is not always the case, but that focus on the couple, or even the focus solely on one person’s pleasure right, like “my husband wants this” or “my wife wants that,” can make them feel like they’re being used like a prop, like physically being used as a prop, or treated like a sex object right? No affection, no conversation, and I think it’s important that if you are checking in with partner, like your primary partner if you’re part of a couple, you are also checking in with this third person right? Really showing concern for their emotional and physical needs. And other things I’ve heard from unicorns, in terms of complaints, is they don’t want to be hunted aggressively right? When they’re just being bombarded with messages as though you’re shooting fish in a barrel again, it feels very objectifying. And the last complaint I’ve heard from unicorns is that they get outed without permission. Couples will sort of use them as a trophy head and say “we did this, we were with this person,” when they’re not ready to be outed. So I think it’s really important that we think about all three people creating this new dynamic, as opposed to it simply being something for the couple.

Brandon (09:03):

I mean I would say that you don’t have to think about the unicorn if you’re willing to pay a sex worker and have the discussion in advance.

Dr. Jess (09:10):

I mean you still have to think about them but yes it’s not.

Brandon (09:12):

I didn’t mean don’t think about them, but what I mean is you don’t necessarily have to you know, if you’re clear about you just wanna focus on your own pleasure or the pleasure of your partner, and not that of the sex worker, could you not then you make that request from the beginning and pay for it?

Dr. Jess (09:28):

Yeah absolutely, but also, always acknowledging I think the humanity and the emotional experience of everybody involved. That’s another topic I’d love to cover and how we can help folks who engage sex workers can make sure that they’re being really good clients. And I know we talked about that in the past with Andrea Werhun from Modern Whore, and I thought her tips were really helpful as well. So I just kind of wanted to put that out there, first and foremost the piece around acknowledging couples privilege and doing something about it and also, I’m not trying to make people feel guilty. You don’t have to feel badly you don’t have to feel guilty. It is natural to want to preserve your relationship. It is natural to want to prioritize your own needs and the needs of someone you already know and love. We just have to remember that this is a whole new dynamic. And so I would love to read some of the responses I got around threesomes from folks, and it’s just this huge range of perspectives about whether or not folks want to have a threesome. So one person says, I’m not gonna say any names, “It’s the greatest gift to give the one you love pleasure,” okay. Someone else says, “I want to try both MMF and FMF, I think there’s a lot to learn about sex from both,” this guy says, “if I want to disappoint 2 people I’ll just have dinner with my parents.” I got a lot of messages from folks who’ve said that they’ve had them, they’re kind of over hyped.

This person says “I’ve had them. And either I’m so concerned about making sure everyone involved is happy or I’m the one left out, so it can be kind of hard to engage three people.” This guy says, “I need to find someone who can last as long as I can so that she can enjoy two guys the same length of time.” That’s interesting, so for some people, I’m sure that’s true, for me that wouldn’t be true at all. Like the last thing, I presume that means like erection prior to ejaculation, I know I make it sound so sexy, I’d be less concerned about how long that lasts. Because there’s lots of other things to be done. Somebody says, “I’ve done it many times. It’s fascinating, love when both the girls sucks and then smooches each other,” okay. “If you’re in a couple make sure you debrief after each time and share any newly discovered limits,” okay, good one. “You might not know your limits the first time, so use each experience as a learning op,” true, true. A couple people just said, “I love threesomes,“ “I love threesomes,” asking me if I want to have a threesome with you, no thanks. And then just reminders that threesomes can be fantastic, sensual time, but everyone should talk first and get comfortable. Another person says, “yes, it’s my dream fantasy to have a threesome. It can be MMF, MFF, love to explore sex always.” Some folks are asking how they can convince their wife, and I’ll suggest you go back to previous podcasts about how you don’t “convince” somebody, you present and discuss. This person says, “I’m not sure I could handle that. I’m monogamous and sex is highly emotional for me,” so I think it’s really good that he knows his limits. Some folks say it needs to be planned and agreed upon first, as to who is doing what, and we’ll get to some of those questions. Oooh, this person says, “three months postpartum I had my virgin threesome with two men, double penetration,” and then they just wrote “fun.”

Brandon (12:26):

They went for it.

Dr. Jess (12:27):

I love it. I love it.

Brandon (12:29):

It’s impressive.

Dr. Jess (12:30):

This person says, “I feel it will ruin things in the long run.” Fair enough, and that may be the case for some people, sorry they added more, “I can’t handle the thought of my wife with another man. And I’m sure the same for her.” So it’s good that you again know your limits. You don’t have to do everything. A bunch of people just wrote, “it’s overrated, there’s a lot going on. I always feel like I need to process a lot after, and like I wasn’t fully present.” That really makes sense to me. Just the overwhelming physical interactions sometimes can be too much.

Brandon (12:58):

Yeah, there’s a lot of comments about, I mean the initial few comments people wanting to make sure that all parties were pleased. I think that’s really, it’s just a much more thought through process that I don’t think I would have been as focused on, if I was doing it for the first time.

Dr. Jess (13:12):

Yeah absolutely it can be very distracting right? Like I hear from a lot of cis men for example, who say that they lose their erection in their first threesome, because there’s just too much going on and too much pressure.

Brandon (13:23):

I could totally see that being the case. And there’s just, I did like the response about wanting to disappoint 2 people right, going for dinner. That was great.

Dr. Jess (13:32):

This person says that they used to plan threesomes earlier on in the relationship, but later they started to enjoy them when they were more random and unexpected, so maybe with experience you can change the way you interact. “I don’t think I could handle seeing my partner being intimate with another person. I’m too insecure.” That’s fair, and it may not be insecurity. It might just be your own values. Lot of people commenting on communication. Somebody says “the Eiffel tower is the best part of the threesome.” It’s the sex position. “I’ve been there, done that, was fun but not something I’d consider again.” If I was single I would do it, but my fiancee would not.” “Can you do it with friends? Can you do it with a stranger?” So I’m going to suggest you go back to the previous podcast in terms of the data around who people are having threesomes with. Somebody says, “It’s a teenage goal. It’s an over hyped experienced. It’s fun one hundred percent, but not life altering by any means.” I would say that’s kind of my experience as well. They say, “most men, it’s their holy grail, they want 2 women.” This person says, “having sex with 2 people means overflowing with pleasure. I get totally lost in the moment. It’s absolute bliss.” This person, this was a unicorn, that says, “I didn’t like having a threesome with a couple. I wasn’t attracted to the guy at all,” and then somebody says “I’m very insecure. I need to work on that first, it’s not where I need to be with my partner yet.” Yeah and I just wanna say that you know, we all are varying degrees of insecure. Like one day, I might be fine with something and another, I might feel really uncomfortable with it. And so you don’t have to necessarily work on that, I mean if you generally are feeling insecure sure, maybe you wanna work on that. But I don’t want there to be any pressure. So then there’s just a whole bunch more about preparing in advance, talking in advance, talking after, and then a lot of people who have done it saying it’s over hyped. So maybe I should put some pulling out on that, it wasn’t really hot, or it wasn’t really worth it?

So just wanted to share some of that kind of raw notes from the community on threesomes, before we get into now, why we are here, which is some of the questions that I think you can consider either on your own with partner or with all three people before having threesomes. I’m just going to go through them, and starting really broadly with why do you want to have a threesome? ‘Cause every damn group I work with, every group in the world, always, always, always, people are asking me about threesomes like my data is one hundred percent. I don’t think I’ve ever done a workshop where I don’t get an anonymous question about threesomes, always. And so my question is, why do you want to do it? Like what appeals to you about it sexually, physically, relationally, practically? So that’s I think an open ended question. So why do you want to do it? What benefits are you hoping to derive from it? What are the perceived risks and costs? I know people who’ve put together a kind of cost benefit analysis table. That’s how I think so that works for me. I know that’s not everybody’s cup of tea. With whom would you like to have a threesome? Like have you thought about that? Do you want it to be a stranger? Do you want it to be a friend? Do you want to engage a professional? Do you know if that person or those people are open to it? How might your relationship with your threesome mates change post threesome? What excites you most about a threesome? What motivates you? What concerns you? Do have any hesitations? What emotional elements of a threesome have you considered? Because you heard in our community response, that a lot of people talked about insecurity, there were also some notes on jealousy and all those things are fine. It’s okay to feel jealous. It’s okay to feel insecure. That happens and we can’t entirely avoid negative emotions. And in fact for some people, those emotions can be a turn on in a threesome. How will you manage potentially challenging emotions should they arise? So like, what if I do feel jealous? Does it mean that it’s devastating? Does it mean that it adversely affects our relationship? Or do I just say, “I feel a little jealous about that. I mean I kind of file that for later,” and may go through it at a later time. Or I know that when I feel jealous, I become so physiologically flooded that I’m just gonna freak out and run away right?

So how do you tend to respond to these these feelings? Do you feel comfortable communicating your desires, boundaries, right? Like what holds you back? Are you good at this? Do you know what you want? How do you want to feel in the threesome? That’s always my big question for people right, what is it you want to feel? What conditions increase your comfort with open communication? I think that’s a really important one especially as you’re engaging with new people or a new person. What makes you comfortable communicating your boundaries? Are there certain triggers that stop you from speaking up? What does your ideal threesome entail right? What is the setting? What is the type of relationship dynamic? Who’s involved specifically? What are the sex acts you want to engage in right? We’re barely kind of scratching the surface here. What are the things you want to do with your hands? What are the things you want to do with your genitals? What are the things you want to do with your mouth? What are the things you want to do with toys? Where do you want to do it? How do you want all parties involved? Like will 2 people play while one person watches and touches themselves or do you want all three people somehow physically engaged? Like, would you feel left out, if I don’t know they were genital to oral, or genital to genital, and you were just playing with their hair or their toes or their chest or whatever it may be? I think we have to think about those specific things. I’m not saying you can plan it out, then it’s gonna go exactly as planned. But if you can at least think about best and worst case scenarios, it can help you decide your desires and boundaries and communicate them. And I think it’s just really important to remember that it’s okay to experience a range of emotions.

 

Brandon (18:38):

When you’re asking these questions, I’m thinking of my own situation, what I’m comfortable with and not comfortable with, and it’s so interesting. Because as you’re talking through this, number one, all of these questions can in themselves become arousing and fantasizing. Like it creates a bit of a fantasy just having that conversation. But you had also made reference to you know, how would you feel if you saw your partner for the first time and you felt uncomfortable, or jealous, or any of those things. And I think even just mentally thinking about that situation kind of for me, puts me into that situation, so I can think about initiating those feelings, so that I can see how I respond, rather than just boom being in the situation and then all of a sudden being flooded with those emotions. So it’s almost for me a bit of a teaser in advance, to be like, “Oh you know what. I’m thinking about this, you with somebody else, and yeah, I’m feeling a little jealous, or I’m feeling insecure.” So now I put myself there and I’m already gauging how I respond, which I think would be a really helpful role playing scenario.

 

Dr. Jess (19:37):

And you’re thinking about it from the, definitely a couple perspective, because that’s our experience, but these questions are for everybody right? So even if you don’t know the two people you’re playing with, you can still feel jealous right? You can easily feel as though you’re not getting enough attention, you can easily feel as though you’re the third wheel, and so again I go back to okay. So what’s the consequence of that? Like if I don’t get enough attention is at the end of the world or do I just feel a little off in this moment? Maybe I lose interest in the threesome. Like what do I do if I’m no longer turned on, because I’m not having my emotional needs fed? And so I think for couples, I would add some additional questions. So we had you know ten, at least ten there to begin with, which take a while to get through. But if you are in a couple you want to kind of think about okay, so how do you anticipate this experience affecting your interactions with one another? How will you support one another before, during and after the experience? How will you make sure you support the third party before, during and after the experience? How will you make sure that you really think about this new dynamic and you don’t just prioritize yourselves? And how will you check in with one another during the threesome? How will you check in with the third right? And it can be simple questions. Like for example you know, I’m trying to think. If we’re going to play with a group of three people, whether it’s a couple and a single, or just three people coming together, a question like how will I know if you’re liking it, right? Or what will you do if you want more? Or you know, what are some cues I can look for in your body to let me know that something feels good? Or in the moment, it can be as simple as do you like that? Do you want more of that? You want less of that? Here or there?

Just giving people options and not assuming. And actually threesomes must be a really interesting one. And I gotta say like, I’ve observed this so many times because again, all of our models of sex come from porn, but especially threesomes. Most people haven’t seen a lot of threesomes. People act really porn-y, right? I don’t know, do you not remember that from seeing that at parties and clubs, like people being a little bit over the top, performative? And I want to be really clear, that’s not a criticism, because if that gets you off then by all means go for it. But what I’m trying to say is that don’t assume that what they do in porn is what you need to do in your threesome right? Because we have to remember porn is a visual medium right? It’s not a physical one. It’s partially audial, but they’re not focused necessarily on what the actors and performers are feeling. They’re focused on what it looks like for the camera. So even the way the three bodies set up, it’s so that you can see angles and perspectives that the camera likes. And in real life, you don’t have to worry about a camera, unless you’re into that.

Brandon (22:07):

Yeah, I mean for me, porn is where I learnt, I saw other people having sex. So my, when I was younger, the way I responded was based on what I saw in porn. Because I didn’t know on my own, how I was supposed to respond.

Dr. Jess (22:18):

So were you like a jackhammerer?

Brandon (22:20):

Yeah definitely when I was younger, it was just like I’m gonna go as fast and as hard as I can. Because that’s what I saw. And clearly, I’ve learned for me, that doesn’t always have to be the way that it needs to go. But I’ve learned that overtime. And I’ve learned that by also picking up on cues on how your body responds. So you asked some great questions, which is when you speak to your partner, or that individual, or the people that you’re having this threesome with, it’s like what cues can I pick up on? But it all goes back to having that conversation in advance, which frankly for me would almost feel unnatural before you even had sex. Sex is supposed to be the spontaneous thing that happens as opposed to a planned situation.

Dr. Jess (22:56):

But what if it’s more playful than that? Like what if you go for dinner for example, and that’s something you want to talk about as well, like are you just getting together for the sex or is there going to be dinner before, or drinks after or snuggling after? And you know I have heard from unicorns who say that you know, when they are with a couple, they wanna feel cared for right? Just like you wanna snuggle after, they may wanna snuggle after.

Brandon (23:17):

I’m not disagreeing with what you’re saying, I do very much like the idea of having the conversation in advance.

Dr. Jess (23:24):

so couldn’t you make it playful at dinner? Or even via text? Like, “what are you into? Like, “what is it you wanna try?” Or “what’s your ultimate fantasy?” Or “what turns you on?” And I think that playfulness can be a really hot discussion. So it’s not necessarily sitting at a boardroom table and going through a checklist of “yes, I accept pinky fingers in my bum, but not thumbs. I accept two fingers on the vaginal canal, but not three. I love when you play with my right nostril but not my left nostril,” like it doesn’t have to be so regimented. Although it can be too, like for me, that wouldn’t bother me at all. I’d be happy to go through a checklist.

Brandon (23:58):

No, but you know, I just like the idea of even the dinner or drinks or whatever it is that you’re doing in advanced, can be the foreplay. Like it can be the lead up, the buildup, so for those, that hour or two or however long, it’s anticipatory right? Like you’re already getting riled up for what will come.

Dr. Jess (24:15):

Yeah, and you’re getting to know one another right? You’re picking up one another’s vibes, you’re picking up on their communication style, and we used, I think we see this all the time, not just for threesomes but for any kind of group exchange, so for example when we’re, the places where couples are hooking up with one another. You know you’ll see couples go to dinner, and then they often you know go dancing after, and then maybe if there’s a hot tub — I don’t know why there’s always a hot tub involved, but there’s always a hot tub for these situations — they go to the hot tub and hang out, and then it’s literally hours of building and conversation and getting to know them, before you actually get down to anything physical, do you notice that?

Brandon (24:54):

Yeah, and you know what, it creates some connection. It creates an environment like I said, the build up, it’s a lot of fun. You made reference to something and I’m just reflecting on it now. The idea of a notch on the belt, or being just another. And when I’ve had people approach me, or us, and I felt like that’s all it is, where somebody approaches you, says something, and then it’s like “oh you’re not interested,” boom on to somebody else. I’ve been like “oh okay, so yeah that was…” I mean again, that was just my response. But it was like, “yeah, that didn’t really feel that great.”

Dr. Jess (25:28):

Like they’re only into you, they won’t even have a conversation with you, unless there’s a chance that you’re going to have sex with them?

Brandon (25:34):

Humour me for five minutes. Have a conversation.

Dr. Jess (25:38):

Well that’s, interesting because you probably don’t experience that much as guy, but as a woman we get treated like that by men all the time right? Like if we’re not giving them what they want, they’re not gonna kind of quote unquote “waste their time on us.” And I think that’s a sociocultural, I guess norm around sex, that you just are working to get to one specific goal, and there isn’t the rest of the human interaction and connection. And I do have a previous episode with Luna Matatas from a longtime ago, where she talks about how unicorns are so often treated that way right? It’s just like they’re being hunted so hard, and so I think that’s something for all of us to keep in mind. Like I will tell you, I remember when I was twenty years old and I had first met you, and like we talked about threesomes, and I admit my only thought was, “how do we make sure we do this in a way that preserves our relationship? How do we find someone who’s a fit for us?” Like nothing on my mind was about a what kind of person, how do I want to make them feel, what are they into? And it was all like fantasy anyway, but I think that it’s just an important piece to remember, that there’s all this privilege that exists within a couple, and it’s obviously not only when it comes to threesomes. It has to do with taxation, it has to do with income, it has to do with how we live. It’s always my rule that if a third party comes out with us, if one of my friends comes for dinner, I’m like “no, no, no, we pay.” If there’s two of us, we always pay. I don’t know, we have dual income, even though some of my friends have partners at home, it’s just kind of the way I think.

Brandon (27:05):

Yeah, I agree. I mean the focus has shifted over time, and I think it’s more of a “I see the human in you.” Which is “I want to be nice to you, I want to make sure that you’re taken care of.” And like you said, if we go for dinner with somebody, I guess I’ve taken your lead on that, which is, if a friend or third person comes along, we’re gonna,

Dr. Jess (27:24):

I mean my lead is always pay. I hate being paid for, like always pay. And so as we have these conversations right, and there are so many considerations here, starting with the very broad about why you want to have a threesome? And how you want to feel in a threesome? To the very specific right, like are you willing to play with the anus? Are you willing to put your tongue here? What is it that you want to do, very specifically? I think I also want to offer the reminder that most people don’t have threesomes right? We talked about that data last week, and there are lots of different things you can do, even with these conversations, to kind of facilitate threesome lite, right? With a partner, whether it’s a long term partner, any sex partner, you simply just talking about it in bed right? Like talking about what it’s gonna feel like, talking about the things you wanna do, talking about the people you wanna do it with. And that can be very intimidating and very overwhelming, and as you said that can give you a taste of how you might actually feel in the moment, and you might say, “okay, I can push myself far enough where this is a huge turn on,” because of the risk, because of the jealousy, because, — not that everybody feels jealous — I’m just saying that’s a common experience, that the jealousy can be a turn on on both ends. And just talking about it, and that can give you an indication of whether or not you actually want to go through with it. There can also be kind of teasing when you’re out in public right, talking about how you’re going to go talk to someone or maybe flirting with someone, in a respectful way, you’re not leading them on or being untoward and they know that. Flirting really varies from culture to culture, like some of our cultures, flirting is very, very, open and normalized. And for others, flirting is something that we have to be a bit more careful with.

It could just be watching a threesome on film, like watching a scene and talking about what you wanna do and how you wanna do it and how you want to insert yourselves. Some people are having virtual threesomes right, interacting with a cam model in a private room. And making sure you pay them generously for their work. It could be that you role play right? So maybe I blindfold you, and I play with my hands and my tongue and a toy, and I make it so that you can’t physically differentiate between whose hands are on you, and talk about how I’m gonna share you, and how we’re going to please you. And the nice thing about fantasy is that you actually don’t have to consider anybody’s feelings, except for the people in the room right, you don’t have to worry about somebody else’s emotional needs. You don’t have to worry about whether you hang out after right? The role play allows it to be whoever’s in the room at the time. For some people, you can go watch threesomes. I have seen hundreds and hundreds and hundreds of threesomes or group situations, I’m not counting them. and for me, whether there’s three of you or four of you or five of you, it’s kind of the same jam, except for that whole couple plus one dynamic, which you have to be aware of. So even just going to a place where threesomes are happening, like a sex club, and not being a part of them but being just in the vicinity of them. And of course doing it respectfully.

There are places where it’s meant to be exhibitionist and voyeuristic, and there are places where people are looking for privacy right? Like if they’ve tied the curtains around a four poster bed, you’re not going to peek through the little slot. But they, you know, there are sex clubs with rooms where there is a one way mirror, where your intended, you know you’re going to be watched. It could be that you don’t wanna have a physical threesome with a third party, but maybe you just want to engage some watching. It could be that you go for an erotic massage — and you can choose to make it non genital right — it can just be erotic, and again when you are working with professionals, please you know, show the utmost respect. Learn everything you can. Go back and listen to the Modern Whore episode of this podcast, with Andrea Werhun, for some perspective on how to honour and really show appreciation for sex workers. And of course, the number one way is to show your financial generosity, because that’s why they’re there.

Brandon (31:12):

Pay. A lot.

Dr. Jess (31:14):

Pay a lot, tip a lot too, tip heavy. So we’ve spent two weeks on threesomes, which we don’t usually do. We don’t usually split the episodes. But I wanted to leave you with this, and what I’m going to do is I’m going to put the questions for consideration in the podcast notes, because I have some additional ones for you to consider as well, some questions not only on why you want to have a threesome but also how you’re going to deal with distressful emotions right? Like are you comfortable admitting to jealousy, insecurity, distress? What makes you feel jealous, insecure and distressed? When you feel jealous, insecure, or distressed, how does it show up in your body? What do you want to do in those cases? How can you self soothe? How can a partner or partners support you? What do you want them not to do? What are some cues to look for in partners, if you are feeling those emotions? So I’m going to put that questionnaire up there as well, as well as a specific questionnaire for couples. And I don’t want to spend all the time on that today, but I can kind of quickly go through it before we wrap up. This is a questionnaire for couples to kind of moderate the threesome within the context of the relationship.

So whose idea was it? Do you feel any pressure? Have you indirectly or directly pressured your partner? What do you hope to get out of the experience? What are your concerns about the experience? What would it look like if it goes well? What happens if something goes awry? Like how will you communicate? How will you respond? How will you manage within the context of your relationship with one another? What do you value in the third party? What type of person do you wanna connect with? How do you feel about strangers, acquaintances, friends, sex workers? And what are you going to do about your couples privilege? Like how are you going to make sure that all voices and all desires are heard and respected? So, I think that there are questions that we can all consider, and then there are some that are specific to couples. So I’m gonna put those three questionnaires in the show notes.

The general questionnaire for threesomes, the one specifically on jealousy, insecurity and distress, and one specifically for couples to navigate with one another. And you can find those in the show notes at https://happiercouples.com, in the podcast section. So with that, we are going to wrap up. Before I do, I want to say thank you again to Lovehoney. They’ve been as I said in the business for many years, awards from the Queen of England, and like Brandon said, I guess she’s freaky and knows her stuff, so do check out Lovehoney online. We’ll put the links in the notes, but also you can use code DRJESS10 to save on pretty much any toy in the business, they’ve got them all. Thanks so much babe, for chatting with me today. And thank you folks for tuning in. We’ll be back next week with a brand new episode.

(33:49):

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