I’m a gay 35-year-old guy in the San Francisco area. I’m heading on a weekend getaway with my boyfriend and two other gay couples. We’re all solid but purely platonic friends — at least so far — but turning this “couples’ getaway” into a group play extravaganza sounds so hot to me. I believe everyone is in an open relationship like us, but we’ve never played with either couple, and I have very limited experience playing with groups in general. How do we test the waters with the other two couples to see if they’re down to clown without making things awkward and ruining the vibe of the trip?

 Weekend In The Country

“We’ve had things like this happen organically,” said one of my sluttiest gay friends after I shared your question with him. “But it’s only happened without advance planning on night four or five of week-long vacations in Provincetown — LOL — after a long buildup of a lot of hot will-we-or-won’t-we?’ tension. And by the time it happened, it was really pretty clear group play was the vibe, and everyone had signaled they were down.”

Like you, WITC, my sluttiest gay friend is in an open relationship — a long-term, committed, wide-open relationship — and he has more experience turning friends into friends-with-vacation-related-benefits than I do (it’s practically his superpower), which is why I shared your question with him. Let’s call him Himbo.

Okay, seeing as you and your partner don’t have the luxury of time — you’re only going away with the friends you wanna fuck for a weekend — what’s the best plan of attack?

“Assuming his friends aren’t a bunch gays with X-rated alts and OnlyFans accounts — and it doesn’t sound like they are, considering this guy doesn’t even know if his friends are open or not — he’s going to need to proceed with caution,” said Himbo. “So, step one is obviously asking the other couples if they’re open, which is a question most gay couples are comfortable answering. And if they are, maybe broach the subject in advance. If all three couples are open and all three couples are down to play as a group — two very big ifs — that will create anticipation, which can be way hotter than just stumbling into things. But even if everyone is open and thinks they might be down, no one can know for sure how they’re going to feel until you all get together. If it’s not the vibe, don’t force it.”

Another reason to talk about it in advance?

“The bottoms won’t be magically prepped at the exact same time without a little advance warning,” said Himbo. “Springing a group fuck session on a bunch of guys and expecting the bottoms to be ready-for-use is something only a clueless top would do. I’m not saying all tops are clueless — I don’t even know if this guy is a top — but speaking as a bottom, expecting guys to be ready to bottom without warning is the move of a very clueless top.”

Anything Himbo thinks you should watch out for?

“Smashing close friends on your first attempt to open your relationships goes one of two ways in my experience: great or horrible,” said Himbo. “Couples who are opening up for the first time are more likely to get in their heads and have some unexpected feelings, so if these other couples have been closed up to now, take it really slow. Another thing to consider is how they’re all going to be trapped in the same house and unable to leave if some feelings come up, which is a little risky. So, maybe leave the fucking around — if, again, it’s the vibe — for the last night. If it goes great and everyone in the group wishes they’d fucked around the whole time, they can schedule another weekend getaway for the group sooner rather than later.”

P.S. I’m sure there are people out there thinking, “The world is on fire and all this Himbo guy can think about is catching dick in Provincetown.” For the record: I asked Himbo about dick, which is why Himbo is talking about dick, but I know for a fact that dick isn’t the only thing Himbo thinks about.

So, what else is on Himbo’s mind right now?

“The strength, speed, and effectiveness of the right-wing propaganda machine in the United States is both fascinating and horrifying,” said Himbo. “I honestly think the internet ruined America and the rise of a Trump-like figure was inevitable. Basically, the internet made it impossible for people to discern between legitimate information and fraudulent bullshit, which paved the way for Trump. I don’t know what to do about it, but here we are, and it sucks. But there’s a lot of dick online, you know, and I’m a fan, so the Internet isn’t all bad.”

 I’m in a pickle. My gay male partner and I have a bonus boyfriend who comes in from LA once or twice a month to see us. I feel the relationship with this boyfriend has run its course, but partner wants to keep it going. This boyfriend prefers me because I fuck him — and when I do, he confesses his love for me. I have texted the boyfriend and talked to the partner about this, but neither seems to get the message. Do I have to be mean to get my message across?

Keeping It Not Dramatic

Whatever you said to your partner and whatever you texted your bonus boyfriend didn’t do the trick. Which means they either didn’t understand what you meant because your meaning wasn’t clear or whatever you said — to your partner and separately to your bonus boyfriend — was open to more than one interpretation and your partner went with the interpretation that allowed him to keep seeing your bonus boyfriend and your bonus boyfriend went with the interpretation that allowed him to keep taking your dick.

Regarding your bonus boyfriend: The impulse to let someone down easy — the impulse to soften the blow — is a commendable one, of course, but let someone down too easily and they might not realize they’ve been let down (read: dumped) at all. So, while it sounds like you’ve been clear with your partner, it sounds like you’ve been vague with your bonus boyfriend in the hope that he will
 do what exactly? Pick up on your subliminal suggestion and think it was his idea to break things off ? Or maybe you hope your partner — who doesn’t want this thing to end — will do the dirty work and let your bonus boyfriend know it’s over?

Sorry, KIND, but you’re gonna have to do this yourself. You don’t have to be mean, but you have to be blunt: “I’m sorry, but this is over. I don’t want to see you anymore — maybe we can be friends down the line, but the sexual and romantic part of our relationship is through.”

Regarding your partner: Is your partner allowed to keep seeing this boy on his own? Or is your partner required to break up with him too? You obviously can’t be expected to keep seeing/fucking some boy you don’t wanna see/fuck anymore, KIND, because that wouldn’t be fair to you. But your partner may feel like being forced to break things off with this boy isn’t fair to him — or fair to this boy, whose feelings also matter. If you and your partner have an “only play with and/or date other boys together” rule, you may need to revisit it. Whether you wind up revising it or recommitting to it is ultimately up to you and your partner. Good luck.

Read the rest of this week's column here! And this week on the Lovecast: A trans guy still has “female” on his birth certificate. He wonders if it’s too dangerous to try to get it changed at this perilous moment, and also if he should be stockpiling testosterone. Dan brings on Diana Adams, the Executive Director of Chosen Family Law Center, to discuss strategy for trans folks.

On the Magnum, a promising study just came out about a possible risk reduction for bacterial vaginosis that treats
wait for it
men! Dr. Jen Gunter, an OB/GYN and expert in vulvovaginal conditions is on to talk about this study- a tiny bit of optimism for women’s health. LISTEN HERE!