To Threesome or Not to Threesome, That Is the Question

Welcome to Friendzone, Jezebel's column devoted to dealing with the valuable people in your life whom you're not humping. Got an issue and looking for guidance? Email friendzone@jezebel.com.

A fuck buddy of mine suggested a threesome and I'm intrigued. I love hanging out with him but our sexual chemistry is meh sometimes. One of my buddies might be into it and while I don't think she'd mind the suggestion, I'd be really bummed if a threesome destroyed my friendship with her for whatever reason. What are things to keep in mind when picking a threesome partner?

TRIGGER WARNING FOR MY MOM: Stop reading now.

A threesome can be a wonderful way to learn about one's personal strengths. Uh, not that I know anything about what you're talking about, of course. I have just heard through the grapevine (my vagina) that a threesome can be a nice thing and that you can learn about your personal strengths, included but not limited to helpfulness, generosity, patience, and sense of humor.

Threesomes can also be sort of non-dramatically skeevy and make you realize, "Hey, this ain't really my thing. I tried it once and now I'm going to move on with my life."

Worst-case scenario: a threesome can be a terrible way to ruin everyone's night or perhaps year. I heard tell of a girl and gal who had a ladyfriend come into their bedroom, and it ended with the girl crying and the ladyfriend saying, "I'm outta here." The friendship was never really the same. I'm not sure how that marriage fared after the big event, either.

Do you like both these people? Do you trust both these people? Do you feel ready and willing to laugh at yourself and to laugh with them if somebody farts accidentally? Can you all keep a secret? Are you okay with a two-girl one-guy situation? (Personally, I have zero interest in being Eiffel Towered – despite this very sweet suggestion—so I'd be far more on board with your situation than with a two-dude dance. Still, I believe that everyone should be allowed and encouraged to engage in the consensual threesome activities of his/her/their choice.)

You sound quite casual about everyone involved, which I think is a rather good thing. Nobody here is married or in a long-term monogamous relationship. Have a chat with both your buddies about this idea and see what they have to say. If it seems like a fun idea, get everybody together, imbibe some sort of beverage, and see what happens! But you must remember to do the safety dance and use protection (I recall one instance in which a condomless three-way produced offspring, which was quite a surprise to all involved). And make sure everybody gets equal attention!

One more thing: I hate to tell you this, but I've also heard that some threesomes can be quite boring. So don't build it up in your head as the be-all, end-all of sexytime. It's just another permutation of adults getting sweaty and sticky together.

I have a beautiful friend, L, who I've known since I was a kid. She has a VERY good-looking boyfriend. I am not the type of person to ever go after someone's significant other or indulge in someone's cheating because I value my friendships a lot more than sex with my friends' partners. The problem is that said hot boyfriend keeps saying comments to me that started out jokingly but have turned into something more serious. I will admit that I have a flirtatious personality but I have made it VERY WELL KNOWN that I'm not interested in him. Lately, the comments have taken a more sincere, less jokey turn. He even said to me the other night, "Should we tell her about us?" I laughed it off, but I think he meant it! He is so sweet in every other aspect except this particular personality quirk. I just don't want his behavior to come between me and L. Should I say something to her? To him?

The next time he says something like that to you, pull him aside and say, "You know I think you're awesome. But you, sir, are being a little bit naughty." (He wants to be naughty, so he'll like this bit. We're going with the spoonful of sugar principle here.) Then add, "I just don't want to ever make L feel bad or think that it's serious. So let's cool it on that kinda talk, okay? I mean, I know I'm a gorgeous babe so it's difficult, but she really matters to me." If he tries to cover his tracks by saying he was just kidding, you can play along and say, "Whew! What a relief! Good talk!" If he doesn't knock it off, that's when you drop the cutesy tone and get real stern and say, "Buddy, I told you to quit it. Stop it. I'm serious." If he still doesn't stop, you might consider telling her what's been going on. But be prepared for him to deny, deny, deny – or, worse, claim that you came onto him. That's why I advise you to try and work it out with him first in a polite, friendly manner.

Or you might just try hanging out with her one-on-one exclusively. But if they're attached at the hip, that might be difficult.

Bottom line: plenty of people flirt without ever intending to do anything. If he wants to stray, he's gonna stray. You just have to let him know it ain't gonna be with you.

I like having sex and I don't feel like I need to wait to "get to know him" or date him for a couple like the other girls at the sock hop. I don't have sex with A LOT of guys, but I do have sex and it's usually with one partner at a time for a few weeks to a month. It's never one-night stands or with people I just meet, but with people I've known for some time. My two best friends like to give me the most annoying shit for it. My girl friend has had sex with two people (we're 22) and my guy friend bones anyone who will take it, but not a lot will, so he's all fucking sour about me getting all the ass. Some call it slutty, I call it being a god damn human being with needs. They don't judge the guys we hang out with for it, but I seem to get all the shit, because god forbid I'm a woman open about liking sex. What do I do to get them to back the fuck up while still getting my kicks while I'm young?

Look them square in the eye and tell them what you told me: "I notice you don't give any of our guy friends crap about being sexual. So cut it the fuck out with me. I'm serious. It's getting on my nerves. Don't shit on my sex cake."

Now as your elder Auntie Sara, I have to remind you to make sure you use condoms and birth control and all that jazz. Do as I say, not as I've sometimes done! (And you bet your bippy I would say this to a boy, as well.) I think it's awesome that you're in control of your own sex life and that you enjoy what God or nature or whatever gave you, that magical treasure cave we call a vagina. I wish I had been so self-aware when I was your age (you know, uh, last year).

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