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 [email protected].

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).