Miss Information: I cheated. How can I get my boyfriend back?

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I made out with a guy in the back of a car — while my boyfriend was driving. How can I make it up to him?

Dear Miss Information,

I have a very basic problem. It's already been beautifully portrayed in the greatest of John Hughes' movies, Some Kind of Wonderful: I am a "Watts," or what others might call "the best friend." I perpetually find myself in friendships with young men that seem healthy and fun at the beginning, but commonly boil down to hurt feelings and lost friendships. It's an unhealthy cycle. It may be due to my natural instincts I love sci-fi, tell pretty sweet dirty jokes, and am still mothering enough to inadvertently create annoying co-dependent relationships. The friendships almost always begin because I try to flirt with a guy, but then it goes tragically wrong and I resolve to have a friendship with them, rather than nothing at all. The most recent "Keith Nelson" was having sex with two of my friends, but professed that I meant too much too him to risk our friendship. (I call bullshit, sir!) I'm determined to make a change. If you could help me find a way to stop talking about testicles when I get nervous around guys, that would help exponentially.

P.S. Everyone should watch Some Kind of Wonderful. It's basically a better-written Pretty in Pink Fuck Amanda Jones

Dear Fuck Amanda Jones

I'd love to say I concur, but I didn't get around to seeing S.K.O.W. until I was in my late twenties, whereas Pretty in Pink was a slumber-party staple. Molly and the gang are pretty much relatives at this point. I do admire Mary Stuart Masterson's fingerless gloves and soft butch haircut.

Best Friend Syndrome is to advice columnists what the common cold is to doctors. It manifests itself differently from person to person; there is no definitive cause or cure; and for some poor saps, it is constant and chronic.

Your letter does contain some diagnostic clues amidst all the fangirl talk. The word "mothering" jumps out at me like a big pair of granny panties waving at the top of a flagpole. There's nothing wrong with being kind and nurturing, but you've got to make people earn it, love. Too many shy or otherwise socially awkward people make the mistake of thinking they're flirting when they're actually being servile. I'd no sooner spend three hours running errands with a guy who hasn't shown any tangible interest than I'd come over with a bucket and a mop and detail his bathroom. And yet I've known a lot of friends who attempt to woo with these kinds of gestures because they're too afraid to take a risk and make a move early on. Yes, you may get shot down, but all you have to lose are extended angst and blue balls. The next time you find yourself listening while he yaps for hours on end about girl troubles because you've got "nothing better to do," stop. You do have something better to do. If not, then no wonder he doesn't want to date you. Don't want to be treated like a mother figure or a camp counselor? Don't act like one.

The next phrase that pays: "It goes tragically wrong." What's that about? The people I've seen who tend to frame their love lives in these terms either get emotionally invested way too early, assume they're being friendly when they're actually engaging in low-grade stalking, fall for the most inappropriate companion imaginable, or some combination thereof. Is that you, Fuck Amanda Jones?

Good flirting involves setting boundaries, thinking about potential consequences, and practicing self-control. This is not to say you must sit alongside your suitor on the davenport, with your knees closed, listening to the Victrola. There's plenty of room for spontaneity and dick jokes. Find a friend who does well at dating and model their behavior. Spend less time with those male "friends" who've fucked you over and use that time to practice on other prospects. It doesn't necessarily get easier, but you will learn more about dating the more you actually do it.

Dear Miss Information,

I got involved with an old grammar-school friend who's married with a young son. I didn't go looking for this. We reconnected after a long period of not being in touch. I knew she was married and figured nothing would come from hanging out together. One lunch meeting, we ended up making out kind of surprising, kind of not. That led to a clandestine dinner date, and then a weekend getaway. All the while she was telling her husband that she was hanging out with girlfriends. Believe it or not, I didn't have sex with her at all, even on the weekend getaway. Something just seemed wrong about it. (Go figure!)

When we got back from the weekend, she decided she wanted to leave her husband. I asked her point blank if she was leaving to be with me or because she really wasn't happy. She said the latter. After she told her husband, he got angry, then pleaded with her to work on the marriage. She said she wasn't sure, but that they could go to therapy together, which she was already doing alone. I decided this was not what I wanted, and told her I couldn't see her while she got her shit together. She asked if I would wait for her and I said I couldn't make any promises. Over the next four months she tried to call, text, and email — all of which I ignored. The more I thought about it, the more I realized what a mistake I had made. I found out through the grapevine that she and her husband were renewing their vows, which I figured was the end of it all. But she's still sending me messages here and there, every few weeks.

Should I just continue to ignore her correspondence? I think her husband has no idea that she's tried to contact me. I almost want to tell him that this has been happening. I don't want anything to do with her. No good will come from it. She really is a mess and I don't need the drama. — The Accidental Other Guy

Dear The Accidental Other Guy

Yes, ignore her correspondence, and don't you dare tell the husband. She'll fuck up again sooner or later and he'll find out on his own. These people are not close friends or family members, which might make it a little less open and shut. Cool it with the grapevine talk and keep heading down that quasi-high road you've chosen.

Dear Miss Information,

My boyfriend and I have been going out for almost a year now. I was stupidly drunk a week ago at a party we both attended together, and consequentially ended up cheating on him while we were driving back home. The catch being that he was sitting in the front and me and Mr. Mistake were in the back. Before this, we'd talked about how much cheating has hurt both of us in the past, and how we would never do that to each other. Needless to say, he's extremely hurt, because I broke his trust. And I am too, because he wants nothing to do with me. What can I do to have him forgive me?  Haplessly Unfaithful To Him

Dear Haplessly Unfaithful To Him,

Get a bus pass? Buy a bicycle? Sorry, I don't mean to joke. I'm just impressed by your stealth. Maybe you were in an Astro van? Then again, cheating is loosely defined. For some it's kissing, for others it's failing to asking for permission before engaging in an threesome. Perhaps you guys were just holding hands.

In any event, I think it's important to give him a super-wide berth right now. Let him know that you love him and that you know you made a horrible mistake, but do it in a way that's as the twelve-steppers say not going to cause any additional harm. Write an email if he doesn't want to see you, or mail him a letter. Don't put an expiration date on your apology, as in, "If you don't talk to me in the next few days, I'll know that you don't want ever this to work." That's manipulative.

Take action. This happened while you were schwasted? Lay off the sauce for a while, or adopt new habits, like pacing yourself and eating a big meal before you go out so you don't get so damn drunk. Unless Mr. Mistake is your conjoined twin, that relationship should be terminated or put on a very long-term hold. Take him off your Facebook. Delete his number from your cell phone. Same goes for any male companions that have caused rifts in your relationship before. You should be acting like you're in a committed relationship, even if you're no longer technically in one. 

We both know none of this is a guarantee that he'll take you back, but it won't hurt.

Readers, have you ever won someone back after cheating? How did you go about it?