Dear Breakup Girl,

One of my project partners, who is also a reasonably close friend, confided to me recently that she likes my roommate. They have been best friends for a couple of years, and my roommate asked her out about a year ago. She told him at the time that she did not want a relationship because she was not yet over another serious relationship she had ended recently-ish.

Last night I found out that my roommate still has feelings for my friend, but he’s bitter that she “rejected” him a year ago. They are still close friends, but he cannot accept the idea that her feelings may have changed.

I didn’t say anything, as I am sworn to both of their confidences. However, I think that they would make a great couple and would be very happy together, seeing as how they’re already close. I’ve tried to drop subtle hints to get them to talk about it or at least tell each other how they feel. I’m either not being direct enough, or they are only hearing what they want to.

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Housing problems from October 18, 1998…

Dear Breakup Girl,

OK. Here’s the deal. I’m 32, and I was dating/sleeping with this 20 year old guy. Now, I live with him, and we aren’t together anymore… Not my choice. So, anyway, any good ideas on how to live platonically with someone you used to sleep with and still want to sleep with who doesn’t want to sleep with you, while staying roommates and paying the rent…. Hmmmm. Pretty long winded huh?

— Amy

Dear Amy,

Actually, no. No, your letter’s not all that long-winded, and no, I don’t have any good ideas on how to live platonically with someone you used to sleep with and still want to sleep with and who doesn’t want to sleep with you while staying roommates and paying the rent. Time to hang the VACANCY sign.

Love,
Breakup Girl

Out of order on September 7, 1998…

Dear Breakup Girl,

Here’s my situation. A few months ago, I moved into an apartment with a really good friend of mine, I’ll call her “Ann.” I liked living with her. We got along fine and we never fought about anything. I’ve always considered her one of my best friends, and although we flirted a bit it was nothing serious, just friend stuff. Anyway, a while back the two of us went out partying and had a bit too much to drink. We got back home…and, well you get the idea.

Normally I think I could handle this. Spending the night with someone doesn’t mean you have to get married or anything. The problem is, we both decided to try and make a go of an actual relationship. I realize this was a mistake now, but at the time it made sense.

Anyway, it was nice for about a month, but now things are really screwed up. In reality, my relationship with “Ann” is at a point were we barely speak to each other. I really have no idea how THAT happened! All I can say is that being friends with someone and dating that person are totally totally different things. It doesn’t help that she’s VERY hard to talk to.

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A twofer from August 24, 1998…

Dear Breakup Girl,

Okay, two questions.

1) Say you were hooking up with (OK, sleeping with) a guy for a month. Literally every night. Also you’ve known the guy for a year, pretty well, and been friends. He gets out of your bed one Saturday morning and asks you what you’re doing later that day. You then don’t hear from him for oh maybe three weeks. Then you call his machine to point out you have a bunch of his clothes at your apartment. Then you find out he’s been going out with his ex girlfriend and a lot of your “friends” know about it and have not told you. Then say you feel really depressed not to mention you feel like a really really big tool. Say you are normally a cool person. What do you do? Thanks, please help, I need it.

Now my roommate:

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News flash: boys are icky, dateline March 16, 1998…

Dear Breakup Girl,

I have recently moved into a new apartment with a guy, we’ll call him “Brutus,” who I hardly knew. Then the first night we moved in together Brutus and I messed around. Three months have passed since then and I feel like I am pretty much “in love” with him or something quite like it. Problem is, I am quickly falling OUT of love with him due to all of the gross little bodily things that you see everyday when you live with someone. I don’t know how to cool things off with him without going through some big, torrid fiasco and someone moving out — I mean I like being his roommate…but not his girlfriend. I just want to quit messing around with him. Oh yeah, also he always tells me he loves me….uh OH!!!! How can I not hurt him??? Please Advise!!!

–Grossed Out By Bodily Function Brutus

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Love moves in on March 2, 1998…

Dear Breakup Girl,

I recently had a new roommate move into my house. What had recently been a household of girls has now undergone some testosterone revamping. When this guy moved in I thought nothing of him, but now I’m finding myself oddly attracted and I think he’s into me to. What should I do, four months to go and I don’t know if I should tell him or keep it to myself and forget him. Help me!

— Romancing Roomie

Dear Romancing,

Living together is generally something people do after they’ve made a commitment. In your case, play it safe. I wouldn’t want something to be over before it even begins; when your ex is your roommate, all of a sudden those toothpaste trails s/he leaves aren’t so “adorable” anymore. Savor the crush — four months isn’t that long — and when he moves out, then you can consider how to move in.

Love,
Breakup Girl

Hitting (on) close to home February 2, 1998…

Dear Breakup Girl,

I was dating a girl and as soon as I fell for her she decided that I didn’t meet her stringent expectations for a man (nothing to do with measurements, I don’t think). A couple of weeks later, my roommate decided to break the “roommate rule.” I walked in to find said roommate and my ex doing their thing in the living room. I am now a guy with no place to go. I don’t wanna go home cause I may find more shenanigans going on. Is it within my rights to kick my roommate out? Are people allowed to date their roommate’s ex? If so, how long do they need to wait before the couch-fest ensues?

— Battered in Boulder

 
Dear Battered,

This behavior is technically legal, but Melrosically tacky (see “The Tacky Factor” in last week’s column). What is within your rights is to ask them to take their business elsewhere. The two of them should have thought of that. They should also have written a letter like the next one.

Love,
Breakup Girl

We trendsniffing BGers have pointed out lots of the ink that’s been spilled over Depression 2.0 and how it’s affecting the coupled-up:  They’re having hope sex! They’re having no sex! They’re bemoaning lost billions! They’re the bargain-hunting betrothed!

And we thought the worst of it was the stories of divorced couples who’ve had to continue cohabitating in their homes lest they lose a bundle on the surreal estate market. But the Debbie Downers over at Alternet have hit upon something just as sucky: the increased likelihood of singles having platonic roommates well past their age-appropriate 20s and early 30s. Possibly even (dum-da-dum-dum!) for liiiiife!

And I read: “For many urban professionals — despite having a good job and a college education — the American dream has been seriously downsized. Instead of hungering for the house with the white picket fence, they fantasize of one day renting an apartment with no one else’s milk in their fridge.”

While the story cites historical contexts for the rise in roommate-dom — everything from the invention of TV dinners  to the rise of women in the workplace — writer Nan Mooney really hits the nail on the head re: just what it is about being a grown man/woman with a roomie that makes one self-loathe:

“But at what point does having a roommate contribute to the fact that we’re still single and lonely? It’s all too easy to get stuck in that twentysomething, no plans, no worries, no furniture kind of lifestyle. The one where you go out for beers with your buddies every Friday night, crash on your futon and never get around to saving for retirement or contemplating a more permanent relationship.”

And, even more bitingly: “It can be hard to cultivate intimacy with someone when there’s a third party on the couch watching Jon Stewart. By our 30s and 40s, many of us are looking for either independence or intimacy instead of some limbo between the two.”

Thus my much-self-ballyhooed quest to “get New York-married” continues. Having become roommated in late ’08 at the age of 34, for the first time since college, I admit that this article has sent a shockwave through my social life. Not sure what to do yet, but I sure know where not to go looking…

Taking over the city really takes … commitment!

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