I can't very well send this email, can I?

Wow. Okay, just… Wow.

Can I ask you to read the part I quoted there, pretending that some stranger wrote it instead of you? I ask this because as a stranger who happens to be a woman, that section is incredibly repellant and insulting.

Why? Because you flat out said that this has nothing to do with her as a person. “I want to replicate [the experience] ASAP.” No mention of great things about her that you like. You want A Girlfriend and you flipped through your mental Rolodex and said, “oh, hey, she’s a chick I know who is single and our contact didn’t stop because of some disaster. She’ll do!”

And for god’s sake, you “won”? You come across as incredibly entitled. Like if you put in the effort or do the right things, you deserve a relationship. Ew.

That theory reminds me of an even more annoying version of this method.

I didn’t include anything about her because I didn’t think it was relevant. I thought it would be too wordy if I starting waxing poetic about all of her fine qualities. Not only that, but I would come across as rather pathetically lovestruck.

If you want to know, here’s the most crucial one: She asked me out (in a manner not entirely light and breezy) after a semester together in which I routinely offered my pithy insights and unique perspective on issues that concerned both of us. She actually appreciated my gadflying. Then, on our dates, I was (among other things) too out-of-sorts to capitalize on that. Instead, I took the advice from friends who advised me to not speak in paragraphs, or be too serious, etc. I didn’t have much to say, and it was awkward.

If I actually did anything wrong (and perhaps there’s just no rapport anyway) that was it.

Since then, I’ve wanted a chance to actually be that guy who struck her fancy.

Also, regarding “winning” with the other woman, you’re damn right I “won”. I persevered, because I knew I was better than the no-good boyfriend she was with at first, not to mention her subsequent fuck-buddy or two. I saw myself as the prize, and fought through the pain, stress, sleeplessness, and frustration, and got what I wanted and what we both deserved.

She’s said as much. She wishes she had been sleeping with me all along, instead of those losers. I left her in better shape than I found her, to put it mildly. We would most likely still be together without our insoluble deal-breaker. I hate thinking about her and her new man together, but I like and respect him, which is why I introduced them, and they are very good for one another.

Do you stand by your judgment, or do I look better now?

I was completely sincere, and it worked. I’m assuming it will be less painful next time. I got her through some bad times, and that’s the inverse of annoying.

I can’t speak for the person you’re asking the question of, but I’m a little creeped out.

A year of pain, stress, and frustration to win a woman with whom you knew you had a deal-breaker? Honestly, it sounds to me like you thrive on relationship drama. Not that’s there’s necessarily anything wrong with that, but just be clear with yourself about what’s driving you.

If you MUST send an email, make it something like, “I’ve been thinking about you and wondering how you’re doing. I’d like to get together and catch up. Reply if that sounds good to you. Best, OLP”

That’s all. No more. And if she doesn’t reply, forget about her.

This is probably the most disturbing thing I’ve read in a dating thread.

I’m not sure what to tell you, except that you are likely to continue to have poor prospects with women until you stop treating them like interchangeable props in a play you are writing about yourself. Now and then you may have luck with the occasional extremely bored or emotionally disturbed woman, but if you want an actual relationship, you are going to do some hard thinking about how successful your plan really is.

Then let me clarify. I was nothing but good to her (M.), and as I thought I would be, I ended up being very good for her. I helped her through some very tough times, not because I expected some kind of reward, but because I can’t act any other way. If I thought she was interchangeable with anyone, I would not have persisted like that. If other opportunities presented themselves during those months (and I was indeed on the lookout), then I would have probably abandoned the pursuit, for my own health and sanity. I do not thrive on such drama, but I thought M. was worth it, and that I was worth it to her, and that with a lot of skill and some luck, she would see how much better I was for her than the jerks she was with.

I’ll say it again: I left her better than I found her, and vice-versa. If given the chance, I will treat B. the same way, with kindness and respect. I kept pursuing M. because I kept getting encouraging signs. Something similar happened with B., off and on, and I was wondering if, by mirroring her behavior when she first asked me out, I could capitalize, with a minimum of difficulty.

Wow. Gross.

Capitalizing? Winning? Proof you’re now a better dater?
If she was really into you, you’d know it, not be wondering?

Don’t send that letter is my vote. If she was a maybe before this letter, I’m thinking it will push her to “Not with a ten foot pole”.

I’m laughing at the idea that you are God’s gift to women, given that you have “gone years without a date,” just considered writing an embarrassingly inappropriate letter to a casual acquaintance who has repeatedly rejected you, count a short lived “sort of” relationship as your greatest romantic triumph, and have managed to creep out everyone in this thread.

You’re a grown up, you can do things however you want. But if you are for real, I suggest you go ask yourself if anyone- anyone you know- who has a healthy, satisfying love life does anything at all like what you do. I promise you, you are way off base with your current line of thought.

You have been perfectly clear throughout this thread. No one has any doubt about what you’re about. You can’t convince us this is a good idea simply because it isn’t a good idea, no matter how many times you explain it to us simpletons who don’t appear to understand you.
We who know you only as code in front of our eyes know you’ll never see this woman again by her own choice.

Don’t send the letter. You’ve sent her enough signals. If she were in the least interested in you, she would have responded already.

By the way, women are people too; not wars to be won, prey to be hunted. You need a major reality check.

Yep – OurLordPeace, I have to ask if you’ve been reading some kind of pick-up artist books or something. Because that’s what it sounds like.

He’s using some of the words, but for god’s sake you are doing it wrong. Pickup artists are about a small investment in a lot of women. Got it? Not single minded focus on a single woman for months on end.

Do what the books say, dude. Go to some bars, start chatting up every woman you see, and eventually someone will think you are cute and want to sleep with you. You’ll get some action and you’ll leave the poor girl you are targeting alone.

Seriously, you’ve contacted her enough times that if she wants to respond she will. Dial it down.

If you absolutely must continue pursuing this girl, wait at least a month. That’s right, a month. If she truly is too busy to reply to your emails, she doesn’t want to see you keep popping up in her in-box.

Then, send a quick note saying, “Hey, I hope your workload has eased up a little. I’d love to grab a coffee sometime; what’s your schedule look like?” Don’t push any harder than that, and definitely DO NOT send her the e-mail from your OP.

If she still doesn’t reply, face the facts. As much as I hate cliches, this one is completely appropriate: She’s just not that into you.

You’ve called, got her voicemail. Possibly she saw your # let it go to voicemail so as not to talk to you.

You left a voicemail and she hasn’t called back. Possibly she just doesn’t want to talk to you and is hoping you take a hint.

You e-mailed and e-vited her and haven’t got a response. Those electronic forms of communication are very easy and feel relatively safe to do, so it’s possible she doesn’t want to talk to you.

She pulled over to talk to you at some point from the safe cocoon of her car…, doesn’t send ANY message to me, plus or minus.

It was two years ago she asked you out? Looks like she may have changed her mind. Based on what I’ve seen of your basic attitude in this thread, maybe she caught wind of some of those issues you seem to have and decided it wasn’t worth the effort.

It’s not a contest. It’s life. She has the right to not be that into you, if that truly is the case.

Also possible: she really is extremely busy and tends to let things fall thru the cracks. Stop haranguing her and let time tell which scene is the real one.

YMMV and I hope San Fran wins the Superbowl

Sounds more to me like OLP cares only for the “win” of getting what he wants, doesn’t give a damn about the other human being involved (she’s just a game to be “won”).

So, to answer the question I posed in the title of this thread: No, I didn’t think so.

I asked for a second opinion, and I got it, and then some. Sending it would be a terrible idea, as I suspected. I really appreciate the confirmation.

This been very illuminating in an unexpected way, since this is the first time I’ve gotten any negative feedback at all regarding my relationship with M. I’ve talked to a lot of people about her, and they all shared the same set of feelings: happy that I got what I wanted and needed, happy that M. had a great experience, saddened that it had to end, and relieved that it ended because of no-one’s fault or misdeeds. The reaction here is surprising and thought-provoking.

M. herself recently sent me a PUA e-book, in order to help me move on more easily. I just finished reading it, and I have mixed feelings. Besides repeatedly referring to women as “girls,” it seems shallow in other ways. I’ve always thought that I need to get to know somebody pretty well before doing anything else, much less sleeping with them, since I don’t want to give any pleasure, in any way shape or form, to someone of poor ethics/taste/etc. With that said, it might be very helpful for situations in which I already know we have crucial things in common.