The Hook Up: Should I lose my virginity in a threesome?

I’m a young lesbian. A few years ago, I was pretty sure I was gay, and after I fooled around with this one bisexual girl, I knew for sure. It was amazing and since that day I have wanted her. I have an opportunity to sleep with her, but there’s a catch: Her boyfriend would be watching and doing stuff to her, basically a threesome, but me and him aren’t gonna do anything. I want to do it, because i want to do it with her, i’m just not sure if i want something like this to be my first time. But honestly I’m a raging homosexual. I don’t think I can wait much longer. What should i do?

Anna says: Rage! Rage, young lesbian against the dying of your virginity. That was for my early 1900s British Lit lovers. Dylan Thomas in the hizzy! OK, fine — nevermind.

I almost lost my girl virginity in a threesome, too. I didn’t have Big Feelings for the gal, however, and after downing a comically large Carlo Rossi jug of wine, she ended up cradling the toilet most of the night instead of me, so I had to lose my girl virginity the boring one-on-one way a few months later. I know, so sad. But don’t cry for me, Brangelina.

From your letter, it sounds like you’re leaning towards “yes,” and I, for one, am never one to talk a raging homo out of having sexytimes. So, by all means, get down and dirty with this cute bisexual. But first, let me bring everyone down with some tedious introspection and potential pitfalls! Wheeeeeeeeee!

If any part of you feels “ick” about the scenario, then don’t do it. The reason I might think twice about doing it with this gal while her boyfriend watches is that the threesome is uneven. It puts all the focus and pleasure, essentially, on her. If you’re into that and he’s into that, then it could be hip-hip-hoogay times all around, but in my experience, the best threesomes are the ones where everyone is into everyone else. But, hey, to each her own.

I’m not one of those columnists who make a big deal out of losing your virginity because, as I’ve said before, I think the whole ordeal is sort of overplayed, but if you have big-minded sentimentality over who you throw down with for the first time, then you might want to wait for someone who will, at the very least, give you your undivided attention.

Also, make it very, very clear what is and is not okay with you (for more on this, read my previous column on threesomes). It’s a little too easy in the heat of the moment for boundaries to get crossed in a not so fun way, and if you’re not prepared for it, then it’ll be harder for you to speak up. For instance, if the boyfriend gets handsy with you, how are you going to feel about that? How do you feel about being watched in the first place? I’m not saying he’s a skeezeball or anything, or that you’ll even necessarily notice his presence, just that you should be incredibly, obnoxiously upfront about your rules so that they are less likely to get broken. One of my girlfriends and I made the mistake of being willy-nilly about where we stood on threesome etiquette, and I found myself very upset when a certain willy found its way to a certain nilly, if you catch my drift.

Other questions to ask yourself. Do you want to spend the night? How would you feel about them having intercourse? Do you want this to be a one-time deal? Is anything off limits? You don’t have to draft up a treaty or anything, but thoughtful consideration around this delicate subject is always a good thing.

Basically, my advice can be boiled down to this: Be sure and be safe. Don’t compromise your integrity for the sake of a roll in the hay. And don’t do it if you think you’ll feel bad in the morning. Otherwise, have fun! Take notes and report back to me.

I moved in with a Craigslist roommate about nine months ago, and we became good friends pretty quickly. He is a straight guy, but he is cool with my gayness. He’s also fun and kind and very giving. He doesn’t have many friends of his own, but he comes out with my friends and me and gets along well with everyone.

Everything was going well until about three months ago. His work situation changed, and he started working from home (he used to travel about half the time and have an office when he was in town). After the change, he was always at home and eager to talk. His habit of looking to me for all of his social activities became overwhelming since he wasn’t traveling, and he would subtly make me feel guilty when I didn’t invite him along to something. I started avoiding him (I know, definitely not the best response). Then we became kind of okay again, but I got really busy and he read it as me avoiding him. Recently, he’s started drinking more, usually alone, often during the day. He is also getting more drunk than he used to around my friends, and he’s not a very nice (or quiet) drunk.

I’m worried about him. I care about him, and value his friendship, but I’ve started seeing him more as a burden lately. I want him to have someone else in his life, besides me. I try and encourage him to do stuff where he’ll meet people (group bike rides, volunteering with all the cute straight girls at Planned Parenthood, etc.) and even give him places and times and he says he’ll do it, but then he always has an excuse why he didn’t go. I try to suggest activities that don’t involve drinking, but those don’t happen either. What can I do to help him?

We’ve made tentative plans to live together next year (along with another friend X) but I don’t want to do it anymore (although I do want to live with X). Is there a way X and I can tell him that without ruining our friendship?

Anna says: You don’t need to ruin the friendship in order to tell someone you don’t want to cohabitate with them. If anything, creating more space will probably save the friendship. I would say your best bet, should you choose to not live with him, which I think is the best decision, is to couch the rejection in concern for him. This confrontation style is known as a S–t Sandwich. (Even though I seem to be swearing a lot in this column, I swear (heh) I didn’t name it). It goes something like this: Compliment – Criticism – Compliment. For instance, “I think you’re a great roommate and awesome dude. But I think we need some space/time apart for such-and-such reason. I know that since we trust and respect each other so much, I could be honest with you about my concerns.” Adapt as much as you want. The compliments are there to establish trust and soften blows.

His drinking problem is probably the easiest red flag to bring up if you’re looking for a straight-up out as his roommate. Also, sometimes alcoholics need a wake up call. Sometimes they don’t know the extent of their behavior until it is thrust upon them by caring parties. I don’t think you need to go full-out intervention on him (nor do I think it’s your responsibility), but by all means, tell him, firmly and politely, that his bad choices are negatively impacting you and you’re not down with that.

What you wrote to me above shows that you have genuine compassion for this dude, and that he’s mostly a swell guy with a few annoying flaws. I don’t think it’ll be too painful for you to tell him that you value his friendship, but that you can’t and won’t be his sole source of social support.

I also can’t help but point out, since I watch far too much of The Bachelor and The Bachelorette, that you’re “not here to make friends!” This is your life and your private space and your sanity at stake. Make decisions that are right for you, and worry less about bruising your roommate’s ego. He’ll get over it, and he’ll (probably) be better off for it, too.

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at annapulley.com and on Twitter @annapulley. Send her your Hook Up questions at askthehookup@gmail.com.

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