Please Advise: Should I take a chance and hit on my best friend?

Nerve readers hold forth on the risks and rewards of college experimentation.

Each week, the inbox of our venerable advice columnist, Miss Information, is flooded with queries. And although she makes a valiant effort, she cannot answer them all. To deal with the surplus, we've decided to turn to you. So, don your spectacles and help this woman out. You can give her advice in the comments below, or, if you'd like to share what you wrote with your friends, on our Facebook page.

by Nerve Readers

Dear Nerve,

I'm a twenty-two-year-old female, and I've only recently realized that I may be a switch-hitter. Luckily, the college I attend is very LGBTQ-friendly, and so far I've felt safe and supported in my sexual experimentation. But at such a liberal institution, it's hard to figure out who's playing for which team. This has only recently become a problem, since I've begun to have feelings for one of my closest female friends. 

"Lucy" and I are extremely compatible and can't help but have a great time when we are together. Lucy, knowing full-well my fluid sexuality, is a very hands-on kind of girl, constantly touching me and at times sleeping with me in my bed. On a particularly drunken night, we made out. (This was, I should point out, initiated by her.) Now, Lucy has never claimed to be anything but heterosexual, but I constantly find myself wondering what her feelings for me are. Despite all my reservations, the desire to tell Lucy how I feel is overwhelming. I'm fully aware that when dealing with issues of sexuality and identity, I'm playing with fire, and that I may risk losing Lucy as a friend forever. But is there a way of having this conversation that minimizes my chances of total defeat? Should I even try to turn this friendship into something more? 

— Lesbianish Girl Beginning To Question

Commentarium (27 Comments)

Nov 25 11 - 1:29am

Hmm. In my experience (which is mostly second-hand, so, grain of salt), when a straight girl gets asked out by another girl, it's usually seen as a very positive thing; flattering even if misdirected. Of course there's the chance the girl will turn out to be slightly homophobic or whatever, but slightly homophobic girls don't usually make out with other girls, and if she's well aware that you've been bungee jumping the Kinsey scale, she probably won't be too shocked if you make a move. I guess what I'm saying is, I think your chances of 'total defeat' are slim -- the worst I'd imagine coming out of a 'hey, would you like to go on a real date sometime?' would be a week or so of you two being a bit awkward around each other.

Don't just try to get with her when she's drunk, that's sleazy. If you take her out to a nice dinner and make coffee or cocoa for her after, you're already a few points ahead of most college-aged guys. And if she says no, she's not feeling it, just be polite and gracious and totally clear about the fact that you earnestly want to stay friends.

Nov 25 11 - 2:20am

Ah jeez, have at it! You're young, you're at college, when is there going to be a better time to take a risk on this kind of a play? So yeah, worst case you lose a friend. You'll lose friends... that's life. If you hit this thing, in all probability, this romance will burn itself out but you will have lived and won't be thinking 'What if?'. Plenty of time for timidness and provarication in latter life. Better stop before I start quoting Thoreau and urging you to jump on a desk and shout...

Nov 25 11 - 2:20am

you need a statement of intent. and you need to be willing to lose the friendship. "I'm attracted to you" is a good starter. Depending on her reaction, you can either move forward or not, or set a boundary that if she's not down then she doesn't need to be making out with you or sleeping in your bed, because to you its not just girl time. Have her decide what she wants back. There are multiple options. 1. try a relationship(if thats what you want too)
2. stay friends, but none of that girly crap that is always ambiguous. Ever seen that family guy episode that recently came out? Literally said you can't get a straight answer out of a girl in her 20's these days. Your friend is that. Ambiguous.
3. total defeat is how you look at it. If you try and she declines, you succeeded because your goal was to try. if you try and she's down then you succeeded and get a bonus.
4. there are 6 billion people in the world. half are female. Im sure 10% of them at least like other females. Thats 300 million women that would consider you. Go look around.

Nov 25 11 - 2:30am

Definitely go for it. If she's kept being so hand-on after finding out that you're attracted to women, it definitely won't bother her to be asked out by you. Actually, from your description, it sounds like she's interested in you too, and maybe just doesn't want to make a move before knowing if you (and she ) are actually into women. Hope it goes well!

Nov 25 11 - 3:35am

Why not simply test the water ...... after a nice evening together say with a smile "It's such a pity you're straight, I would totally date you......." and see where that lands......that gives her the chance to light heartedly shrug it off or...... :-)

Nov 25 11 - 12:26pm

Agreed. That's what I've done in the past, and it's worked well for me!

Nov 25 11 - 12:41pm

I like this idea best as well!

Nov 26 11 - 1:57am

My favorite suggestion so far too!

Nov 26 11 - 12:42pm

Change "date" in that sentence to "do". Speaking from experience, it's a lot easier for female friends to recover from a sexual encounter than a brief dating/relationship scenario where one of them decides, nah, she's not actually into girls that way. I have been occasional snuggle buddies with a couple friends who turned out to either be too straight or too closeted to go further emotionally, and those relationships are fine, but few friendships will survive the drama of College Lesbian Relationship!

You guys are already really close and it sounds like it's mainly the sexual piece of the puzzle that you're curious about. You already have a relationship, go for a very cards-on-the-table sexual advance first.

Nov 28 11 - 2:47pm
experienced bi

Agreed its easier to recover a friendship after a sexual tryst, than after a 'serious' romantic acceleration.

Nov 25 11 - 3:45am

You have nothing to lose. Seriously, nothing can be lost here if you go for it. Worst case ontario, she shoots you down and you feel embarrassed. And that happens to us all.

Go all in and hope for the best. That's all you can do.

Nov 27 11 - 4:42pm

you're most of an optometrist than a pessimist.

Nov 25 11 - 4:46am

If you are not sure how she feels about female homosexuality, why not just bring up the topic one day while you're just having casual conversation. I suggest that you maybe start off the conversation with something positive about that kind of activity, because people are rarely honest about these things and usually go with what they think the people listening would more accept. If the conversation turns out to be positive move slow, maybe along the lines of mutual exploration instead of a type of relationship. You've already made out so maybe bring up that situation, because usually people do things when they are drunk so that they would have an excuse of why they did it if the feelings were'nt mutual.

Nov 25 11 - 5:53am

Hey, I fell in love when I was in college, and it cost me a lot. Lots of friends, a smooth academic path, family -- you get the idea. For a college kid, big stuff. And I was heterosexual. So I say: many people who love have risk. Just because it's gay doesn't mean the pathos is extra serious. If you mean it, go for it. If you feel sorry for yourself more, you're not in love.

Nov 25 11 - 8:04am

This is absurd, the fact that you MADE OUT makes this very easy to answer. She's obviously open to the idea and you should absolutely proceed.

Nov 25 11 - 1:32pm

Heterosexuals do not make out with people of the same sex. Sounds like you're free to sin away if that's what you want to do, but you really shouldn't.

Nov 25 11 - 1:59pm

"...constantly touching me and at times sleeping with me in my bed..."

So where's the confusion again? Did you write and send your submission without re-reading it? Allow me to reiterate: "...constantly touching me and at times sleeping with me in my bed..."

Now lets try that on for size again, "...constantly touching me and at times sleeping with me in my bed..."

Nov 25 11 - 3:57pm

sorry that doesn't necessarily mean she's down for serious girl-on-girl action. sometimes hetero females just like to test the water. its thrilling for them. and then they think about licking a pussy and they bail.

Nov 26 11 - 3:52am

So true. The story of my life.

I'm sorry, letter writer, I am the absolute Queen of failed Heteromance. The straight girls love to kiss me for funsies.

Nov 26 11 - 12:49pm
hearts and darts

I'm in the same boat as you two. And homegirl's friend sounds like a tease.

Sometimes, letter writer, and you'll discover this more and more as you get older, the straight girls like to get a rise out of us lesbianish types.
Lord knows why.
She probably knows you're attracted to her, and she might want to experiment herself. But there's also the chance that she doesn't want to get down with the get down, and she just likes the attention.
That's the real question we're dealing with here. I'd ask her as part of some casual conversation if she could ever see herself being with a woman.
Even if she says yes, there's always the chance that if/when you ended up in the sack she'd turn ice-cold. But that's the risk you run with first-timers.

Nov 25 11 - 4:32pm

If you were two males, I'd say go for it!

But I know a ton of straight girls who have made out with each other when they are drunk, and it means nothing. Heterosexuals DO make out with one another on occasion, and it's much more prevalent between women than men. It's not unusual for women to sleep in the same bed in certain situations.

Love between friends is a terrible idea whether its a guy and a girl, two guys, or two girls. Go find another girl to hook up with and see how you feel.

Nov 25 11 - 7:56pm

"Please Advise: Should I take a chance and hit on my best friend?"


If she dug you like that, you wouldn't be friends.

Nov 27 11 - 6:44pm

Good advice!

Nov 26 11 - 10:26pm

I would consider trying to make out with her when she isn't drunk. Rather than confessing your feelings, simply lean in for a kiss and see if she finishes it. If not, well then you know your answer. If so, she might just be trying things out. Continue to experiment with her, but wait till your completely sure she is up for some girl on girl before you confess your feelings. Let the physical attraction that you two already obviously have develop and mature before adding feelings into it. I think your friend is still just unsure of how she feels.

Nov 30 11 - 10:31pm


Dec 11 11 - 5:01pm

I would have a 'talk' with your friend. If there's no mutual attraction it ends with a talk and two friends, if it's there then you haven't missed an opportunity.