It should be the easiest thing in the world!

April 11, 2010 9:39 PM

I'd like to date my best friend. We've known each other for four or five years, and hang out once or twice every couple of weeks. We're very close, and talk a lot on the phone or online. We both find each other attractive. So my question is, how do I best segue from this platonic relationship into a romantic one? If it goes badly, say if he tells me I've totally misinterpreted the tenor of our relationship, what can I do to patch things over? And - does anyone have any success stories? Thanks so much.
posted by anonymous to human relations (19 answers total)

Previously, previously...
posted by Jaltcoh at 9:49 PM on April 11, 2010

The other anachronism and I were friends for a year or so, housemates (with my ex for the first six months) for two years and now we're married (all up it's about 9 years, 5 of those partnered, 3 married, also have a 10 month old baby). So we're a success story. The key attributes to that success? We never ever ever use anything from our pasts against each other. Seriously. One of my exes is his best friend and that has never come up in an argument. Ever. When you've got a lot of shared history that isn't romantic you need to work out how that's going to fit into your relationship. We see it as a foundation, not a pinnacle. It's super easy to fall into bad habits when you've spent so long being friends that I think actual concrete and concious work is vital at the beginning. We deliberately took it slow even though we were already living together.

The catalyst for the change was both of us realising that the other was more important than we'd previously thought. So we awkwardly talked about it and got flustered. Slept on it, decided to give it a try and he promptly went on holidays for a week (organised and booked prior to the relationship talk). It meant we got a little bit of time to really synthesise how much things were going to change. Luckily we're both fairly open emotionally and we were in a solid place so we didn't freak out at any point.

As for patching over if it goes badly - time and more time, and then a bit more.
posted by geek anachronism at 9:53 PM on April 11, 2010

I feel like we get asked this question all the time...

And my stock answer is, try gradually upping the ante. Be a little flirtatious. Sit a little closer. Reveal a few details about your past sexual encounters. If the other person is interested in you, he or she will respond in kind. Alternatively, if the other person is withdrawing or seems uncomfortable at all, back right off and go back to being strictly friendly with him or her. The idea is to be subtle enough that if the other person should turn out not to be interested, you can go back to former state of affairs with no damage done or awkwardness and without forcing the person to reject you outright.
posted by orange swan at 10:10 PM on April 11, 2010 [5 favorites]

I've got two examples. Boy #1 I met when I was 15. He rapidly became a good friend and we were each other's confidantes through relationships, school, etc., although he lived a couple of hours away. We wrote volumes to each other, spoke long distance infrequently because of the expense.

Boy #2 I met when I was 17. We also became good friends. After about 8 months we became lovers as a result of an awkward conversation during a long walk when B2 confessed he was a virgin and embarassed. I suggested he needed not a lover, but a good friend with whom he was already comfortable, not realizing he'd already chosen me for the job.

The ups and downs of this were related to B1 who was also in a serious romantic relationship.

B2 eventually Found Religion and called off the sex. I was devastated as I'd fallen in love with this friend. We didn't speak for a month or so and then he left me a birthday present by my door. I called him, we spoke more, became good friends again.

About this time I wrote a letter to B1 suggesting we move our relationship forward. We'd been friends for 2 or 3 years by this point. He was concerned I was rebounding from B2. I said I wanted to have B1's children. Circumstances were such that about another year later we were in the same town for a week and we tried it out. We were hooked.

B1 and I got married a few months later, when I was 20 and he was 23. B2 couldn't come to our wedding but met us on our trip west for breakfast and wished us joy. A few months after that B2 came to visit us to tell us he was gay. B1 and I have been married 30 years.

B2 and his husband are the godparents of our kids. They married after 25 years together and my sons and I went to their wedding. My husband couldn't come with us. But I count myself blessed that I married one good friend, and slept with, got over, and am now best friends again with another good friend.

My experience is that if you are truly friends, becoming lovers will be awkward but satisfying. If it doesn't work out, good friends forgive each other and return to their friendship. YMMV.
posted by angiep at 10:26 PM on April 11, 2010 [2 favorites]

I've done this. We were very close and had a contact pattern similar to yours (although we had known each other a year instead of four years), and I had no way of reliably knowing how expressing my romantic interest would go.

The best way to segue to dating is to not overthink it and make sure you do it. When I went about this, I tried to make my move on two different occasions. Both times, hours and hours had slipped away, and I'd driven her home without having said anything. "The easiest thing in the world" it certainly is not. So, a couple hours after the second freeze-up, I texted her what I meant to say in person.

Worthy of the Smooth Moves Team? No. Still, I got the idea out, and it turned out she was interested. We've been enjoying the #1 relationship of our lives (as in, the top of the heap and deserving of italics) for over three years.

The alternative, I figured, was to freeze up several more times (which was likely because I couldn't explain how it was happening) while she got together with someone else.

So, I think the best way to make this happen is:

- Don't wait for a perfect moment or a perfect method of communication.

- Don't come up with some sort of elaborate strategy to test the waters or ask them out without directly asking them out. Anything that's not "ask them if they're interested in a romantic relationship" is likely not really a strategy, but rather, an excuse.

- Don't talk yourself out of this. You're likely a thoughtful person, and you'd be happier dating this friend. You're close, and you know your friend is not a cold or vicious person (I assume - if this some crazy vampire friendship, none of what I've said applies), they won't abandon you simply because you had feelings for them. The only thing you have to lose is embarrassment, which is temporary. Your potential gain is far more significant than that.

- Good luck!
posted by ignignokt at 11:00 PM on April 11, 2010

I recently told a very close (read: we live together) friend I have a crush on him. He doesn't feel the same way, but we're both rational enough to not let it get in the way of our friendship. It's like nothing ever happened, really. Go for it.
posted by hipersons at 1:17 AM on April 12, 2010

Here's a success story, from the male point of view. I've been the guy in your exact situation. My friend made the first move - I let her crash at my place one night (something I'd been doing for a while on a purely friend basis) and she just looked me in the eye and said she had feelings for me. That was a good night. There is no perfect moment, I think it would have actually been more awkward had it been all planned out.

Of course if you look at my posting history you'll see that relationship didn't work out quite so well. But you totally can and should worry about that later. I know it's probably one of the big fears you have - what if I screw up the friendship? You won't, or at least telling a guy you like him won't. Don't let that fear get you down. It's like being afraid of flying. You envision a explosion but it's highly unlikely. Subtlety is for chick flicks.
posted by wonnage at 1:57 AM on April 12, 2010

My approach has always been to tell someone that I have a crush in a lighthearted but sincere way. As hipersons pointed out, this kind of revelation doesn't have to make things awkward between the two of you if the feelings aren't mutual. Chances are that he'll be flattered even if he doesn't want to pursue a romantic relationship. I have also almost always ended up romantically involved with the person I've told, though this quite often happens some time later. Sometimes you just need to plant a little seed for things to grow.

You could also ask him if he's ever had a thing for you.
posted by inconsequentialist at 2:01 AM on April 12, 2010 [1 favorite]

I once told my husband that I wasn't interested in him when he went out on a limb and told me he was 'into' me. I meant it! I swear I did! As inconsequentialist said, sometimes you just have to plant a seed.

As others have said, you don't have to let this be awkward. If it doesn't work out in your favour right away, you can prove this by moving forward with your friendship and forgetting about it. Keep it sweet and simple and don't beat around the bush. Just get it over with and you will feel a lot better. You can always laugh about it later, right?

Good luck!
posted by sunshinesky at 5:40 AM on April 12, 2010 [1 favorite]

(we were roommates, btw, so the stakes were higher in my case... be happy if you don't live togehter, one less thing to worry about)
posted by sunshinesky at 5:41 AM on April 12, 2010

I have a success story that I love to share! We were friends for 7 years before we got together. He had a crush on me when we first met, but I wasn't in a place to reciprocate even though I found him attractive. Over those 7 years, we shared an amazing friendship, travelled together and supported each other through it all. One day, the crush came back, but this time with me on him! We had a little bit of a bumpy ride from best friends to "more", but it worked out and today we are happily married with a beautiful baby boy.

My best advice is just be honest with your feelings, be sincere and risk the hurt. It may not work out the way you want it to, but your best friend should always be given your honesty and sincerity.

Good luck!
posted by murrey at 6:18 AM on April 12, 2010

I dated one of my best friends a few years back. We had been friends for six or seven years at that point, but the interest was mostly on my part. I pursued her for about six months, then we were on-again-off-again for about six months, then she broke up with me for good. We didn't really speak to each other for almost a year, but we're now friends again. We've both since dated other people, and I've learned to tell the difference between close, deep friendship and romantic attraction.

If I'd been more mature then, I'd never have made a move. You don't have sex--or initiate a relationship where such is possible--with your friends. It's a category mistake. If I'd handled things differently, I could easily have lost one of my closest friends. I did for that year or so, but even once we started talking again it was almost another year before things were really back to normal.

Montaigne has a famous essay on friendship which is really worth the read. The main thesis is that friendship, unlike romantic attraction, is enduring, not subject to fits and starts, and is not subject to satiation. Sorting out eros from phileos is hard, but it's worth it.
posted by valkyryn at 6:37 AM on April 12, 2010 [1 favorite]

For what it's worth, the way this has always worked for me is that there needs to be a gap in between. I don't know if it cleanses the emotional palate (to give the friends a chance to spend a little time apart and start up again in a different fashion) or if it is pure happenstance, but this is how it goes with me.

Everyone I have ever dated was someone I knew first as a friend for at least a year (with a single disastrous exception). Sometimes much more than a year... wendy BD and I worked together at a job in university in the mid-eighties and now are living together quite happily.

However, we didn't see one another for a decade or two in between. In that decade or two, I was involved with a number of people whom I knew as friends for some time, then drifted apart from for whatever reason, then found myself crossing paths with again on very different terms. Usually it has been a gap of at least three years with no contact before we intersected again.

Maybe it is because we always started off as friends before that I am on good terms with just about all of my exes now. There are one or two I have lost touch with, but most I retain a solid bond with; even with one where it ended very badly, she was not totally gone. A few years after we went our separate ways, I suffered a family tragedy and this woman who was living abroad and had not spoken to me in five years sent me a very nice note and called a couple of times to see how I was doing.
posted by ricochet biscuit at 8:24 AM on April 12, 2010

XKCD may be able to help. Don't be that guy. Say something. One way or another, you won't regret it.
posted by violinflu at 8:36 AM on April 12, 2010

If he is interested in taking things to a romantic level, don't put too much emphasis on being In A Relationship at first. Just take it slow and see how you relate to each other romantically. In my experience, turning friendship into more is often unsuccessful long-term, but it can work if you don't put too much pressure on it. Hell, I'm living a success story right now. We were best friends and roommates who sometimes slept together. Eventually we realized we were crazy about each other, but even after admitting that, it took a good couple of months for us to go from, "Okay, I'm pretty sure I'm in love with you" to, "I love you and want to be in a committed relationship with you." That period was a bit painful -- we were in a sort of relationship limbo -- but it was worth it because we were slowly opening up to each other's love, allowing ourselves to be more affectionate, getting daily glimpses of how it would actually be if we were together. By the time we were ready to make it official, we knew it was right.
posted by spinto at 8:53 AM on April 12, 2010

A few options that have worked for me to go from friend -> doin' it

1. Stealth date, then kiss him
2. Take your shirt off, then kiss him
3. Have a couple drinks, tell him he looks hot, then kiss him
4. Have a couple of drinks, lie down on a couch, then gesture for him to come lie down next to you with your finger (like, c'mere) then when he does, put his hand on your chest and kiss him
5. Tell him you think he's hot and that you want to make out with him, then kiss him

You get the picture! All of these moves (and some combos) have worked to get friend relationships to hot sex relationships! YOU CAN DO IT!

Also, sometimes the guy is like "wut" but then you just gotta shake it off or at least pretend like you're shaking it off then go cry where he can't see you. That will preserve the friendship.
posted by internet fraud detective squad, station number 9 at 9:20 AM on April 12, 2010 [2 favorites]

I'm a fan of saying something directly, because having sex and being in a relationship are not the same thing: you can have sex without it ever turning into a relationship. And since sex often ups the intensity of everyone's emotions, if you go into it with differing, unspoken expectations, some one usually ends up getting hurt.

And as I have discovered somewhat to my chagrin, people can have very selective memories. I have at least one friend who I hooked up with in odd circumstances--at a New Year's Eve party in a different city than the one we normally live in--and it was so out-of-character for both us that we've never really talked about it. So, hooking up doesn't necessarily make everything clearer, although it can.

That's why I'm in favor of talking, or writing, or texting, or whatever. Don't worry about the ideal way of saying something. Figure out the medium you are most likely to use (and be honest with yourself: if you pick the medium the ideal version of yourself would use, you'll never do it). I think it's better to say something imperfectly than to never say it at all.

And keep it short and simple. If he says no, it's much easier to continue on with your friendship if all you've told him is, "I'm interested in you." It's much harder to carry on as normal if you've told him, "I think I've been in love with you for years and years. Before I go to sleep every night, I kiss the picture of you I keep under my pillow. And I realized I was in love with you on the 21st of January 2007 when you showed up at my house wearing particularly fetching orange socks." The idea is to keep it casual enough that you can pretend it's not a big deal if he says no. If he says yes, there will be time to tell him later about the names you've picked out for your future children.
posted by colfax at 12:44 PM on April 12, 2010 [1 favorite]

I have a "we tried it and it failed but we're ok!" story. I've been friends with X guy since freshman year of high school (we're now 25). We met at the Halloween Dance- I was totally excited to meet him because he had dressed up like a plague victim! How cool is that?! He liked me then, I wasn't into him, cool costume aside. In high school and college we both dated other people but stayed close. In November 09 he was on leave from the Peace Corps and we were both like, "Wanna try stuff?" We'd been nagging one another about it for years, mostly in the form of bravado and put-downs. We ended up making out and both decided we have the chemistry of a wet dish rag. The kissing sucked so bad we couldn't even go further lest it get more awkward.

We've talked about it since and been honest and now it's relegated to an important learning experience and horrible makeout. Now back in Kazakhstan he's completely infatuated with a Russian girl and he wants me to be Best "Man" at his future wedding. I'm happy to do it and we both know you don't necessarily have to marry your best friend. Go for it but be prepared to handle the consequences. Good luck!
posted by ShadePlant at 1:21 PM on April 12, 2010 [1 favorite]

I have been in this situation before... It didn't work out the way I'd hoped at the time, but after I talked to him and shared my feelings (and learned he didn't reciprocate), I was able to eventually move on to the single happiest relationship I have ever been in. It might be awkward after you broach the subject, but is that better than wondering what might have been, or holding out for something that might happen someday?

I believe that it is better to know and have (hopefully temporary) awkwardness than it is to put your life on hold in the name of something that might not be there.
posted by getawaysticks at 6:50 AM on April 13, 2010