I wish I had asked you out instead.

October 18, 2011 3:05 PM

Does it ever work in the wrong order?

Has anyone ever gone from roommate (with someone you weren't friends with first) to dating, and had it work? I have a serious brain crush (not just lust) on a new roommate (and he's attractive and age appropriate to boot), and it obviously seems like insanity to ever cross any boundaries that would threaten a comfortable living situation for both parties. For what it's worth, I've had a long run at co-ed living situations and never had this problem come up before. Have I ruined my chances of ever dating him by signing a lease with him? Is a future relationship even possible if you started OUT living together? Has anyone else had experience with this, or advice?

posted by anonymous to Human Relations (33 answers total)

It's going to be much safer to attempt this after one or the other of you moves out. If you try and it fails, living together is going to be hell on wheels. You might get lucky and find that it works while you're living together, but those are some long odds you're playing. Much safer to have somewhere you can get away from this person from.

Think about it: would you want to live with someone who had an unrequited crush on you?
posted by Solomon at 3:13 PM on October 18, 2011 [2 favorites]

Give it time before you do anything. In a way, living with him will give you a kind of rare preview of what it's actually like to be with him. A few months should help you tell if there's more compatibility than a simple crush there. (Not that there's anything wrong with trying someone out based on a mere crush in general, but a roommate situation is the exact wrong context for that.)
posted by threeants at 3:16 PM on October 18, 2011 [2 favorites]

A good friend of mine started dating a roommate. They were friends first, for quite some time. They got married a year later and are one of the happiest couples I know.

However, if it doesn't work out (or if he isn't mutually interested), this may become a hellish living situation. I'd only try to move forward if you are really sure that he has feelings for you as well.
posted by DoubleLune at 3:18 PM on October 18, 2011 [1 favorite]

My cousin started dating her roommate. Now they are living together and very serious. You'll never know unless you try...
posted by zia at 3:23 PM on October 18, 2011

I am the product of roommates with benefits. Seriously. The relationship didn't work out thought, so I can't give you specific advice from my experience.

I think give it some time as roommates, but definitely bring it up in a couple of months if you still feel this way. Who knows, your crush may fade, or it may not. He may be interested or he may not. Know that if he's not, one of the two of you will probably (although not necessarily) have to move out.
posted by arcticwoman at 3:23 PM on October 18, 2011 [1 favorite]

My sister married the guy she fell in love with when they were roommates, and they are still gushingly, stupidly happy together. So it can work.

But it could also go terribly, horribly wrong, and you really don't want that.

Definitely give it time, like several months to a year. And I guess I'd recommend against making any moves unless you're pretty sure he's on the same wavelength, preferably when you're both within a month or so of deciding whether to renew your leases. At least that way one or both of you will be able to move if you make an advance and it's not reciprocated.
posted by vytae at 3:31 PM on October 18, 2011

There's an Ask thread about this situation, with some follow-up apparently indicating that it did in fact work out.

Anyway, I think you already know that this is a situation that can of course work out, but brings with it many complications, and could go poorly. You need to decide whether you want to maybe try it (or try to try it), and then you need a strategy for managing potential fuckups.
posted by grobstein at 3:39 PM on October 18, 2011

Yes, it's possible. I've got a friend who is now engaged to his former roommate. They aren't living together only because he got a job in a new city-- they went straight from roommates to dating/cohabitating to engaged.

However, I think it's really really rare. I know a bunch more people who got into *very* unhappy situations when they started messing around with roommates. So, get yourself armed with an escape plan first, in case things go pancake-shaped, and then see what happens.
posted by nat at 3:41 PM on October 18, 2011

I say go for it, just be prepared to (and make sure you can) bail on your living situation immediately if it goes south.
posted by MillMan at 3:46 PM on October 18, 2011 [1 favorite]

Define "work".


I had a few roomates date once. They lasted over a year and then broke up and someone had to move out, which is the down side. Unless it ends up just a quick fling then someone's going to have to move if/when the shit goes south.
posted by bitdamaged at 3:52 PM on October 18, 2011

I've got a couple of good friends who started out as roommates (of each other and me too). They've been married for about 13 years now. I can think of another couple of friends who lived in a group house together who also wound up getting married. So clearly it can work.

I'd say go for it, but have an escape plan.
posted by adamrice at 4:01 PM on October 18, 2011

My very dumb roommates started dating. I was shocked at how dumb they were to risk their healthy happy living environment. I was a groomsman in their wedding two years ago.

While I hate to admit I was wrong and it can work out...it worked out and they are happy.
posted by Felex at 4:03 PM on October 18, 2011 [1 favorite]

Coming up for ten years with my roomate turned boyfriend.
posted by Wantok at 4:07 PM on October 18, 2011

My cousin is currently in a relationship with a former roommate (from a house of maybe 4 people) - they were roommates/friends for a long time (maybe a year or so?), then they got together, then eventually they lived together in a second group house, and now they are long distance for grad school but still going strong as far as I can tell. I would say give it time first, but it does seem to work out sometimes.
posted by naoko at 4:08 PM on October 18, 2011

My friend got this same situation to work. However, she had been living with the guy for about half a year before she got up the courage to make a move. I would suggest taking it slowly to make sure your crush is the real deal and to get a feel for whether this guy likes you back.
posted by vanitas at 4:33 PM on October 18, 2011

For my own roommates and friends, it's usually been a disaster, or best case, shrug it off and return to being friends.

For one couple, they got together and it was a disaster (as the other roomates, we were trying to figure out which one of them to kick out, or just both), I think broke up and it was a disaster, got together again and she moved out, and after dating living in different houses for awhile, once they were stable, they moved in together, and now they've been married for a year or two.

So, hmmm.
Make of that what you will.

One problem is, if you live together, it turns super-serious, super-fast. They are there, all the time! Once you sleep together, it tends to be in the same bed, all the time.
So often what should have been a less than 3 months, and part ways amicably relationship, ends up being a 4 year relationship that isn't working most of the time, because of the inertia of living together.
posted by Elysum at 4:40 PM on October 18, 2011

Almost 4 years ago, I wrote this askme.

Had a baby. Want more. How much better could it go?
posted by sunshinesky at 5:50 PM on October 18, 2011 [3 favorites]

My friends did this! The guy is a Mefite so I won't say more. But it seems to have worked out awesome.
posted by sweetkid at 5:59 PM on October 18, 2011

Well, if the debate is moving out and then trying to date or just trying to date while living together and moving out if it doesn't work, doesn't it make more sense to try?

Just make sure you have a contingency plan in place for if it doesn't work (who moves out, etc)

My parents met as housemates.
posted by Raichle at 6:15 PM on October 18, 2011

That is how my parents met as well. I think they more went housemates -> friends -> dating though. They have been married for 33 years.
posted by magnetsphere at 6:23 PM on October 18, 2011

I think I would be more afraid that it would go well. Then you're suddenly in the living together mode before your second date--yikes! (For some of the people who did this... Separate rooms? Did you schedule dates? Did randomly sitting around watching TV count?)
posted by anaelith at 6:49 PM on October 18, 2011

Just had my 15th wedding anniversary with my roommate.
posted by little miss s at 7:22 PM on October 18, 2011

I did this! Moved into the same room after about 2 weeks. Got engaged after 12 weeks, and have been married 7 years. We had never met before she moved in, and were "plain" roommates for about 9 months. Then we got drunk. (it's more romantic than it sounds.)

I say, go for it! At least you'll have an interesting response when this question gets re-asked in five years.
posted by hammurderer at 8:40 PM on October 18, 2011 [2 favorites]

I've done it. It was fine. We eventually broke up, and right around then the landlord sold the house and we all had to move out. Convenient.
posted by Joseph Gurl at 8:50 PM on October 18, 2011

I married my hot, funny, sweet, upstanding roommate 2 years ago; we've been together for 5 years, stupid-happy in love through hard times as well as the good (and I stand by my advice in the thread sunshinesky linked to). It's not destined to go badly any more than any other romantic chance you take necessarily; the issue is IF it does go badly, as any dating can, you have a lot more of a mess to clean up in the aftermath. But it's not inherently doomed or anything. My advice would be to pace yourself/watch yourself and have a sense of what would happen if it doesn't work out/exit strategy at least considered ahead of time.
posted by ifjuly at 9:15 PM on October 18, 2011

Seen it work, seen it fail. Just like meeting people in the real world. Go for it. There will always be a place to live, but love, much harder to come by, no?
posted by Ironmouth at 10:12 PM on October 18, 2011 [1 favorite]

I'm living with my ex-girlfriend due to us both being on a lease (and me being a brokearse grad student who can't afford to buy out the lease and/or pay double rent). Even though we're on pretty good terms, it's still an amazingly uncomfortable situation for me. I'm not saying don't try it, but consider the consequences.
posted by Alterscape at 10:23 PM on October 18, 2011

I'm pretty sure that alcohol is going to be involved in this situation ... not that that's a bad thing.
posted by Capri at 6:49 AM on October 19, 2011

I divorced my former roommate about 7 years ago.
posted by getawaysticks at 7:19 AM on October 19, 2011

I think I would be more afraid that it would go well. Then you're suddenly in the living together mode before your second date--yikes! (For some of the people who did this... Separate rooms? Did you schedule dates? Did randomly sitting around watching TV count?)

Personally, I went in super wary of doing just that (going from 0 to 90 live-in couple just bc we happened to be sharing space already), so initially we had a lot of mutual understood boundaries like yes, maintaining our own rooms (to the point of, for a while, sleeping separately even after, ahem, bedroom shenanigans), not necessarily keeping the same hours (we still "set things up" like you would with any friend or early girlfriend/boyfriend, even yes, just watching TV), not being domestic by default (like, we didn't eat meals together unless it was something planned as if a dinner date would be at one another's separate abodes). It sounds cold maybe, but I am super glad we took it slow and let things unfurl at the right emotional pace despite the chance of accelerating a lot of stuff out of convenience. It was about letting things happen in pace with our emotions, not rushing headlong into things with a lot of bonding weight before we were ready. And when we WERE ready, we'd talk about it (one of us would just say, hey, I was thinking maybe we could start doing X. What do you think?). It might seem a little more awkward when you already live together to have to negotiate that, like it's artificial boundary setting, but it worked for us. I didn't want a situation where suddenly this guy I had butterflies for but hadn't been with long enough to trust a lot was like my nuclear family, that intertwined in my daily life and wellbeing, just because the roommate situation comboed with the romance made that default. (I'd recently been burned by entering into that level of domestic intimacy too soon with an ex, so I was perhaps especially mindful/protective.) What was great about that was when we DID gradually let the domestic pieces fall, it was totally earned, mindful; I KNEW it was good because I actively chose to say "yes" when the time was right, with little doubt in my mind, which gave me confidence and faith in our relationship, which in turn made it strong.
posted by ifjuly at 12:41 PM on October 19, 2011 [1 favorite]

I remember what a big deal it was when we merged grocery shopping lists, ha.
posted by ifjuly at 12:42 PM on October 19, 2011

I met my current girlfriend when I subleased a room in her two bedroom apartment. She is eight years older than me, and due to this there were no romantic inclinations in the beginning. I dated another girl during the first two weeks of my stay with her.

We got along well with eachother and began to spent leisure time together. Three weeks later we went on a long weekend bicycle tour to the country. During the trip, on a very cold morning, we had a very passionate cuddling session. We spent the day holding hands, told eachother that we liked eachother, and had sex that evening. We've been dating nine months now and are making immigration plans.

One thing I have to say about this: the transition has to be based on mutual respect. If you end up just sleeping with eachother out of physical desire, things will go south when one party wants a relationship and the other just sex. In other words, scope him out and make him attached to you emotionally, before making a move.
posted by BeaverTerror at 7:21 AM on October 20, 2011

PS. I just read Ifjuly's reply above. We didn't do any of that take-the-time thing. We were already sharing groceries prior to dating, and when we came back from the bike tour I never slept in my room again. I'd just come out of a four year relationship three months prior, so I was very comfortable with the shared domestic arrangement. She was a little weary, but in the end we are just fine.

In case it matters. I am a 23 year old man. She is 31.
posted by BeaverTerror at 7:28 AM on October 20, 2011