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 threesomes and discuss couples’ privilege.

Check out the questionnaires below, and be sure to check out AdamAndEve.com and use code DRJESS50 to save 50% off almost any item with FREE shipping + VIP rush processing.

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…

Threesomes: Managing Jealousy, Insecurity & Distress

• 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…

Threesomes: Couples’ Questionnaire

• 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?

And if you have podcast questions, please submit them here. You can find the podcast on Apple Podcasts, Spotify, Podbean, Go<wbr />ogle Podcasts, Amazon Music & Stitcher!

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 337

How To Plan A Successful Threesome

[00:00:00 ] Brandon Ware: Welcome to the sex with Dr. Jess podcast. And I’m looking at Dr. Jess with a giant smile on her face.

[00:00:05 ] Jess O’Reilly: You like that? It’s a Terry Crews smile.

[00:00:06 ] Brandon Ware: I do like that smile.

[00:00:08 ] Jess O’Reilly: Okay.

[00:00:08 ] Brandon Ware: Why are you so happy?

[00:00:09 ] Jess O’Reilly: Because you walk past my laptop just now and I shut it. So you wouldn’t see what was on it.

[00:00:14 ] Brandon Ware: I, nothing shocks me.

[00:00:15 ] Brandon Ware: Nothing surprises me.

[00:00:16 ] Jess O’Reilly: It’s not porn.

[00:00:17 ] Brandon Ware: Does it?

[00:00:18 ] Jess O’Reilly: It’s not. I mean, obviously not.

[00:00:20 ] Brandon Ware: If it was, I’d been so shocked.

[00:00:21 ] Jess O’Reilly: It’s for research purposes.

[00:00:23 ] Brandon Ware: Yeah, me too. Research.

[00:00:24 ] Jess O’Reilly: No, it was an article that I didn’t want to go to about the Scandinavian sleep method.

[00:00:30 ] Brandon Ware: Okay. I’m a Scandinavian. I’m going to just assume minimalism, hard woods.

[00:00:36 ] Jess O’Reilly: You just sleep on flanks of wood.

[00:00:38 ] Brandon Ware: Yeah.

[00:00:39 ] Jess O’Reilly: No. So, so it’s this trend that has been popularized as of late on the TikTok. On the TikTok. Where you sleep in a double bed or a queen bed or a king bed. Okay. A matrimonial bed, as it’s called, and you sleep with separate comforters. So you share a bed, but separate comforters.

[00:00:57 ] Jess O’Reilly: And it’s my greatest fear that you’re gonna see this and want to do this.

[00:01:01 ] Brandon Ware: It’s, it doesn’t bother me at all because

[00:01:04 ] Brandon Ware: I don’t, I’m a human heating machine.

[00:01:06 ] Brandon Ware: Don’t you know this? After 23 years, I I, I have, I’m just, I’m a heating machine.

[00:01:11 ] Jess O’Reilly: I know, but does coming close to me get you too hot?

[00:01:14 ] Brandon Ware: Yes, absolutely. Don’t you notice that you’re like spoon me and then I’ll come over, I’ll spoon you, and then 30 seconds later, I’m like, okay, I’m sweating now I have to leave.

[00:01:21 ] Brandon Ware: And don’t you ever notice I temperature regulate with my leg, the single leg, and it’s like getting too hot. Leg goes out, give me five minutes, body cools down. Is

[00:01:32 ] Jess O’Reilly: it one leg or is it either leg? Depending on which side you’re on.

[00:01:34 ] Brandon Ware: I