The question

I'm in my mid-20s. My girlfriend – well, ex-girlfriend now – who I went out with for two years, broke up with me a year ago. But then, she turned around and wanted to be "friends." We go to movies, have drinks, dinner, sit on her patio and talk. The problem is, I still find her very attractive, still want to sleep with her and am probably a little bit in love with her. The other problem is that recently she started dating a close friend of mine. It's torture to me to see them together. What can I do? I feel like I'm in hell!

The answer

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Well, purgatory, certainly, at the very least.

I've been in that shadowy netherworld myself. When I was in my mid-20s, I dated a 19-year-old waitress/bartender. She was voluptuous and sexy. I don't know if we had a lot in common intellectually, but I really had the hots for her.

Our relationship only lasted a few months. But the postrelationship relationship lasted a full two years. She teased me, she tortured me to the brink of madness with the casual sadism of a teen.

She would change in front of me. "Oooh, it's time to go to work, I better change." Suddenly she'd be in bra and underwear in my apartment. Sometimes she'd be "too drunk to go home" and stay over in my queen-sized bed.

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And sometimes, she'd throw this dog a bone, thus ensuring I stayed on a very short leash, following her around town like a panting puppy, hoping for my reward.

Who knows why people do this? Good for their self-esteem, I suppose. But the problem with these kinds of arrangements is that the amount it boosts their self-esteem is commensurate with the extent it erodes yours.

As to your friend, he is in violation of what we called in bachelor days the Five Year/Foreign Country clause of the Friend Code: "Though shalt not date a close friend's ex until a period of five years hath elapsed, or you encounter her/him in a foreign country."

Draconian, perhaps, but the Friend Code was and is aimed at preserving friendships. And this is the type of situation that can cause them to implode.

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What I would do in your boots: First of all, never, ever, hang out with them as a couple. That is, to use a couple of new-age neologisms, "self-harming" behaviour. And you want to practise "self-care."

Personally, I would avoid your friend for now, too. I'm not saying turn your back on him. Just put him in "the penalty box" for a while. Partly for violating the Friend Code, partly because he's bound to remind you of your ex. At least for now. You need a complete media blackout on your ex, so you can begin to forget about her. They say "absence makes the heart grow fonder," but I don't agree. "Out of sight out of mind:" That's the cliché that will set you free. (In my case, my ex thankfully relocated to Los Angeles to become a writer/actress.)

Now, I could speculate that in your heart of hearts you hope to win your ex back. I would let that go. I've seen that these break-up-date-someone-else-get-back-together arrangements can work – for a while. But the second iteration never seems to work out in the long run.

It's telling, I think, that you called her your "girlfriend" at first, then corrected yourself. You have to let go.

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It's not just a question of self-esteem. Being hooked on an ex – the dopamine shot you get when you see her – it's like any other drug.

It can ruin your career, even your health … (My ex used to get off work at 2 a.m. – then want to begin her evening, partying with all the other restaurant workers. I'd go with her. I had to be at work at 8 a.m.!)

You want someone who will love you for you, who will know you and understand you down to the ground and love you anyway. The sooner you put this relationship with your ex in the rear view, the better for everyone.

Are you in a sticky situation? Send your dilemmas to damage@globeandmail.com. Please keep your submissions to 150 words and include a daytime contact number so we can follow up with any queries.