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The question

My girlfriend of over two years unceremoniously dropped me while we were on vacation with my family. I was crushed. I asked her to tell me why. It's true I said and did a dozen stupid, insensitive and selfish things. But I've done a hundred thoughtful, sensitive and kind things too. She won't hear of it. But she keeps texting, calling and inviting me over, but with clear, off-limits boundaries. What to do?

The answer

We take pains not to reveal the identities of the people who write in to this column, but I hope this questioner won't mind me mentioning he's a doctor.

I have to admit it colours my answer, a bit. Because while my information may be out of date (I've been out of the game 20 years now), last I heard an eligible bachelor doctor might not have much trouble in the dating jungle.

Ladies: Am I wrong? Am I somehow being sexist and retrograde?

But before I release you from my advice-clinic, Doctor, your test results show three distinct and separate ailments in the situation above that should be nipped in the bud before they metastasize into something more serious.

First, you complain about being "unceremoniously" handed your outpatient papers by your ex, and hint at dissatisfaction with her choice of venue.

But what's up with that, doc? Truthfully, I never understood people who focus on the manner, tenor, verbiage and venue employed by someone who's dumping them. What's the difference how they do it? They're saying they don't want to see you any more – quite possibly because you're so critical and want to argue about everything. Now you're going to be critical of how they dumped you, and argue about it?

Look: Breakup scenarios are always going to be messy. You and your ex are both emotional, upset and human. Mistakes are going to be made. Best not to dwell upon it. Let it go, like a patient that simply couldn't be saved.

The second condition I am able to diagnose is her trying to push you into "The Friend Zone" without a suitable period of mourning/recovery.

That's something else I never understood: people's mania for staying "friends" with exes. If there was any passion, heat, and seriousness to the romantic relationship, there's bound to be a commensurate amount of anger, bitterness, and regret in the aftermath – not a good spot from which to launch a friendship. "Laughter is not a bad beginning for a friendship," Oscar Wilde said – right, as usual. Most of my friendships began with laughter. Someone says something you find funny, you think: "Hey, that's my kind of gal/guy." Whereas friendships with exes begin in tears.

I know some people manage to stay friends with their exes. So fine, but if you want things to work out, wait at least half as long (in your case a year) as you went out before you essay platonic pal-hood.

Or maybe I'm being too math-pants – basically, wait until you are well and truly over her (and ideally fully ensconced with another woman), or it'll just be sheer torture. You know the type of thing I mean: You yearning, her yawning. You mooning, her telling you about her date last night. (Like the annus horribilis of erotic torment I spent with a girlfriend – a bartender/waitress with whom I had nothing in common except we both thought she was sexy. After we broke up, we became "friends," as in she'd sleep over and change in front of me.)

Final symptom of post-relationship illness: your contention that doing some "thoughtful, kind, and sensitive things" negates all the "stupid, insensitive, and selfish" actions during the relationship.

Wrong. That is a fundamental misdiagnosis that will lead to romantic malpractice in your future.

Look at it this way: Your ex didn't feel the one outweighed the other.

In short: Forgive your ex for how she broke it off. Give the wound time to heal before attempting to become friends. And finally: Physician, heal thyself and try to be nicer the next time a girl admits you to the clinic of her affections.

If you do these things, the prognosis for your future romantic health looks positive.

What am I supposed to do now?

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