Long time reader, first time writer. And I should probably begin by saying I'm pretty fucked—in the sense that everything has kinda blown up in my face. I should start at the beginning.

I was in a very vanilla relationship with a woman for nine years. A woman who I loved and who really loved me. The problem was that we were more of less friends who fucked sometimes, and there was never a real passion or urgency. We literally went the last year we had together without sex. I didn't know how to turn her on at all. And I greatly felt I was not her type. There was no spark. I found a spark with a girl met and really fell in love with. The catch is that I remained with my girlfriend-in-name. I tried to be a supportive father figure, I guess, to my girlfriend-in-name while also trying not to be a distant, fly-by-night asshole to my girlfriend-in-my-heart.

Then my girlfriend-in-name discovered a package from my girlfriend-in-my-heart. She exploded and cut bait, moving across the country within three days, returning to her family. I see now that I was a chickenshit coward and I tried to tell her I still loved her. And I did. I do. But I couldn't find a way to tell her I loved someone else too. She's gone now.

While I was focused on my girlfriend-in-name—while we were talking whether or not we should breakup—my girlfriend-in-my-heart became increasingly impatient. I'm sure she was waiting for me to make my choice. Then the choice was made for me and my girlfriend-in-my-heart took it personally. I was in a bad place, mentally and emotionally, and I sometimes iced her out and I didn't feel sexual or in a place where I could be a boyfriend to anyone. So I sent the girlfriend-in-my-heart a letter explaining I needed to break up with her because it was all driving me crazy. She took it badly and showed the letter to her therapist. Her therapist confirmed that, yeah, I was probably right and that I wasn't good boyfriend material at the moment.

Time passed and I got my wits back. But my girlfriend-in-my-heart grew colder and more distant. Unbeknownst to me she was dating guys on the side. And on her birthday she told me she was making it official with one. I know I was the one who broke up with her but it hit me like a sledgehammer. I feel terrible now because she really was somebody I truly loved and I didn't realize it until she was was gone. She says she's happy with the guy she's with now but I feel like a pathetic lost puppy. I'm still talking to her, now more than ever, desperate to prove to her that the slap-in-the-face wakeup call was all I needed to realize I should have put her first all along.

My question is: Should I cling to the sad, small morsel of hope I'm still holding on to? The hope that I can stay with her again? Or should I give up and try my luck with someone else?

Awaiting Your Response

You really screwed the pooch there, AYR, and I'm not confident this pooch can be unscrewed.

You have two ex-girlfriends. Ms. Name probably wanted out a long time ago and the existence of Ms. Heart gave her the push/grounds/victim status she needed to end things with you. Ms. Heart, your other ex-girlfriend, was no doubt wounded when you ran after Ms. Name despite your protestations of love for Ms. Heart and the obvious dysfunction/disconnect that characterized your relationship with Ms. Name.

Why did you pursue Ms. Name after she dumped you? Probably for the same reason you stayed with Ms. Name after it was clear your relationship was doomed: you wanted to be supportive and you wanted to be kind, i.e. you're invested in being perceived as a good and decent guy. I'm thinking it killed you to know that Ms. Name was at home complaining to anyone who would listen about what a fucking two-timing piece of shit you are. (Ms. Name most likely neglected to mention the fact that you two hadn't fucked in a year, that she wasn't really that into you or attracted to you, and that you might have grounds to cheat.) Only by winning her back could you redeem yourself in the eyes of Ms. Name and her family.

But let's suppose you had won her back. What then? In time you could reclaim your good-and-decent-guy status, I guess, but at the price of re-trapping yourself in a passionless, urgency-free, sexless relationship.

So what do you do now that you've realized Ms. Heart—sigh—is the woman you wanted to be with all along? (Something you only realized once Ms. Heart ran off with someone else.) Do you cling to hope—most likely of the false variety—or do you try your luck with someone else?

Yes, AYR, you do that—you do both of those things. Live in hope you might hear from Ms. Heart someday ("Would you like to grab a drink and catch up?") while at the same time getting out there and dating other people. You may never hear from Ms. Heart again, AYR, you may be with someone else and completely over Ms. Heart when she calls/DMs you, or you may be between girlfriends when she calls DMs/you.

In other words: don't rule out the possibility of getting back together—if she calls you (you shouldn't call her)—but don't wait for her either.

Good luck, dude.