Miss Information: I think I’m falling for my best friend’s girlfriend.

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Dear Miss Information,

I’m a guy who recently split with my girlfriend of eleven months. I had been in love with her for eight years prior to dating her. She, my two best friends (who happen to be dating each other), and I had a Valentine’s Day party/movie marathon at her place. At the end of the night, I ended up going to bed with her. The next morning, she was emotionally distant; she wouldn’t even let me hug her.

Now she is dropping hints that she wants to get back together again. Here’s the big problem: I think I’m starting to like my female best friend — the one who is dating my male best friend.

I see the potential here for ruining all three of these six-to-ten year friendships in one fell swoop. They’re my only friends. I can’t stand being alone, but I can only date people I know very well. I just don’t know what to do here. — Confused and Alone

Dear Confused and Alone,

It’s not strangers you don’t want to date. It’s attainable people who actually like you. You were all about your girlfriend, for eight long years. Until you finally caught her. Now that one epic, intimacy-delaying quest has been achieved, it’s off to another. What’s more challenging than going after a best friend who also happens to be a best friend’s girl? Too bad she’s not also in prison, then we’d really have ourselves a trial.

Please know that I’m not trying to blame you, shame you, or any other negative turns of phrase that could be turned into a rhyming couplet. You’re close to these people. I get it. Feelings develop. I’m just challenging you to take several big steps back and try to deconstruct the source. Here are few thought-starters:

– Why did you break up with your ex-girlfriend?

– What are you doing, other than hanging out with her on major romantic holidays, to move on and get yourself over it?

– What is it about this female best friend that you find so amazing? Could it be the relationship she has with your best friend instead of the girl herself?

– What about the danger factor? Would you be as into her if she was just a random girl you met on the street and it wasn’t so taboo?

– If the woman of your dreams suddenly appeared out of nowhere, with no work or effort on your part, would you still want this girl?

– What if the Valentine’s Day sex never happened? Is it possible you’re looking for an easy escape route? (My guess is if your ex gets wind of your crush, she’ll definitely stop pursuing you, no discussion required.)

I’ll stop here. It’s a lot to think about. If I were you, I’d do what I can to avoid trigger situations with all three of these people. Cancel your plans for a Memorial Day sleepover until you’ve had some time to get your head back on the way it’s supposed to. Monk out for a while or go on some dates. You can date people you don’t know. You’re just afraid and don’t want to. Challenge yourself. There was a time you didn’t know these core friends/co-dependents. Emily Dickinson said, "My friends are my estate." They’re also one of the few things in life that are free, so don’t limit yourself to a one-room studio.

Dear Miss Information,

I’m male, newly married, and twenty-seven years old. Growing up, I always had far more female friends than male friends, especially in high school and college. Now I live in a small(ish) city and work full time while my wife finishes grad school and works part-time. The opportunities for meeting new people are limited. There are a few women at my work that I’d like to try to establish friendships with, but they always seem to turn me down or make up excuses. Why? Aren’t we past this? How can I convince them I’m not looking to get laid, just someone to go out to lunch with or the occasional happy hour drink. My wife is cool with me having these friendships. Why are these women so closed-off to me? I feel misunderstood and lonely. — Female Friendless

Dear Female Friendless,

They’re not friendly to you for the same reason cloying calendar shoots and News of the Weird stories are the only places you’ll ever find mice buddying up to felines. It ain’t natural, Female Friendless. It goes against what we’ve been told is appropriate behavior for single and married people, not to mention people who share an office and live in a small town, where rumors and bullshit easily take flight.

Don’t assume it’s you that’s the predator. If I were the female in this situation, I’d probably be more afraid of your wife. I know you. We tell funny jokes by the microwave and it’s cool, but I haven’t met the missus and I have no idea what she’s all about. Will she toast me with a cup of eggnog at the next company Christmas party or treat me like a husband-stealing Jezebel?

In order to build these friendships, you have to establish trust, Female Friendless. It might not be fair, or gender utopian, but in this situation it’s absolutely required.

The first step is making friends with both males and females at your office. Go out in groups and keep the gender mix as even as possible. You may not like all of the people you’re inviting, but it doesn’t matter. You’re not there to talk to them. They’re just buffers. Plus, you might find that, despite the faux hawk and super annoying phone voice, you actually enjoy talking to Todd from Accounting.

The next step is to get to know these women as part of a couple. Go on double dates or grab some after-work drinks and encourage everyone to bring along girlfriends, boyfriends, husbands, and wives. If the women you’re trying to befriend are single, have them bring along some friends. You could bring one as well. Nothing says, “Don’t worry, I’m not trying to fuck you,” like, “Have you met Stephen, my hot single friend?”

Now that everyone’s met everyone, and transparency and trust have been established, the friendships you’ve been missing out on will most likely follow. That’s assuming none of the parties involved have been deemed “too aggressive” or “too flirtatious” or “too more-attractive-than-me” by someone else’s partner. That’s a risk you take when mixing your work and not-at-work lives.

There’s also the possibility that these women just don’t feel like they click with you. Do they initiate conversations and call you by your nickname, or do they pretend to be talking on the phone when you walk by their cube? Be careful that you’re not convincing yourself that your marital status is the culprit when signs say otherwise. Finally, remember that work is just one of many places to meet people. If that’s not true for where you live, consider moving to a bigger city when your wife finishes grad school. You’re young. You don’t have kids. Now could be the perfect time.

Married/cohabitating readers, do you have opposite sex friendships at work? How did they develop?