Ask her out on a date. Good luck dude!
That’s understandable, but seriously, that proposed message has “insecure” written all over it. “I like you, do you like me?” So weak.
I just don’t understand this seemingly universal male proclivity to write out these long-ass explanations about how you were so fucked up or whatever.
Keep it light and keep it simple: “Hey. Haven’t seen you in a while. How about drinks sometime?”
gigi it certainly does make me cringe.
I get the idea to keep it light and simple. If I were to actually send a message, I probably would trim it down and say what some of you have suggested. The only reason I would say what I originally intended was to show that I can be more open and forthcoming than how i had acted previously.
But I’m not going too. There’s way too much history to ever make a healthy relationship. But I still have a desire to send this against better judgment. Why?
Furthermore, what would your reaction be? On the surface, it’s just a harmless email. But, in reality, it’s filled with emotion and propositions.
Keep in mind, there is no bad blood that I am aware of. I’m sure that she liked me at one point in time. It really just amounts to a string of missed opportunities.
What’s the history that makes you think you guys can’t be in a relationship? Do you mean that if it hasn’t happened yet it will never happen? It sounds like you have never even tried. She talked to you a few times and then you stopped talking to her for some reason.
What you are saying happened, and this attitude of “it’s all so fraught and doomed” don’t match up. It is something that is obviously a big deal to you, but I can’t see where it is a big deal to her. You seem scared, which is understandable, but you don’t need to decide it’s all hopeless from the start.
Just ask her out, without the drama, and proceed from there, without the drama. As far as I can tell you seem to be making up reasons why that’s a bad idea even though it is what you want to do. Just do it.
This is the best way to handle it. Period.
Because your letter makes this:
… obvious. Most girls don’t like it when guys are “obsessed” with them. It’s creepy and/or off-putting.
Girls like a confident guy. Your message exudes a lack of confidence. Asking her out for coffee, and maybe mentioning that you’d like to catch up or smooth things out, sounds assertive and has a much lower ick factor. If she does like you, that should certainly do the trick. If she doesn’t, you’ve probably just saved yourself a heart-squashing (and we all know what that feels like).
I wish you the best of luck. It’s not easy out there. The best advice I can offer for finding love is just to echo what others have said: stop looking and focus on yourself. Figure out what you have to offer the world, and develop that. Girls will LOVE you! 
What’s wrong with the above? Why the need to send a ‘desperation’ plea. The beauty of asking her out is that you will know right away if she’s interested. If she is, great! If she’s not, no biggie… just move on.
I’ve never understood why “no” was such a crushing blow to guys. Everyone won’t be for you. The way to weed them out is to ask.
For you I recommend “Without Embarrassment - The Social Coward’s Totally Fearless Seduction System” by Michael Pilinski. The official site is at highstatusmale.com.
I recommend “01 Lesson: Beautiful Women Prefer Nerds!: A Real Man’s Guide on How to Find, Date, and Romance the Perfect Woman” by Ross Quigley for advice about relationships. It has better advice than the impression you’d get from the title.
Stop making it all about you. If you like her and you think there’s a chance, ask her if she wants to chat, or if she’d like to go out for a drink/coffee/whatever, then pay some attention to what she says.
Stop framing it in terms of what you are and what you want.
No it’s not. Look up the definiton of “simple.”
“Would you like to get together (or go out) for coffee (or drinks/a movie/whatever)?” is a simple message. Note that “I like you” is implicit – otherwise why would you want to see her?
“I know this may sound weird” + “I like you” + “Do you like me?” + “I feel like I’ve messed up” + “I don’t always mess up” + “I like you” + “Call me” + “I won’t stalk you” + “I’ve been pining” is not, repeat NOT, a simple message. Nor, I’d venture, a welcome one. ETA: Nor is it actually asking her out. It’s dumping a bunch of thoughts on her without even saying the one thing that needs to be said in order for anything to happen! Either ask her out or don’t, but don’t soak her in an emotional flood.
I was just struck by the OP’s parenthetical note “Via Facebook.” I’m not sure quite what that entails, but I’d certainly choose a communication method that is not accessible by anyone but the young lady in question.
Add me to the chorus of no votes. Imagine that you have a daughter and she got an email like that, you might be a little leery of the guy. I say keep it light, just ask if she wants to meet for a drink sometime and catch up on things. If she accepts, try to read her face to see if she has any romantic interest.
I will go against the grain and tell you to send it, with some caveats:
"Hey I know this is out of the blue but sometimes I think about you and I was wondering if you ever think of me too? I just always really liked you. Anyways, if you ever wanna talk again feel free to give me a ring or text or something. "
Editing mine. Keep it simple, and send it. Otherwise you’ll always wonder “What if?” At least if she thoroughly rejects you, you’ll know and can move on.
No point in sitting in your room pining.
^
That pretty much entails sending a letter though, no? Although, if sent unedited, how much of a difference would it really make?
I also vote for “send with edits.”
See, the thing is, I don’t want to just ask her out. At least, not right away. I literally have probably asked her out over a dozen times since I’ve known her but its never worked out. That’s basically why the light-hearted route probably wouldn’t work either. I’ve tried it and its failed. At this point, I just want to talk to her. I’d just like to show her i have the courage to put it out there rather than hide behind a veil of passive-aggressive desire.
I highly doubt I’m going too in any case. I doubt ill be sending my message or a light-hearted one. Like i said, logically, I get that it’s a bad idea. I can’t pinpoint why though?
In essence, it would just be like an email. I would just be telling her how I feel. It’s not threatening or mean. Some of you are saying it’s not “confident” or “assertive” but what makes you say that? This would be coming from deep in my heart and is the realist thing I could say while trying to maintain some level of light-heartedness.
Gary T, you can send a private message via Facebook. It’s very much like an email. I thought a message such as mine would be better suited for that than text or a phone call, and I don’t have her actual email.
The abovequoted illustrates why it’s hard to answer your question. What you said above makes it sound like, not only should you not send the message, you really shouldn’t even be in contact with her at all. But since you’re not following that route, it seems you probably know a lot more about the situation than we do (and that, of course, is completely unsurprising). And in light of that it’s hard for me to think I can have anything useful to say to you by way of advice. I have no idea what kind of relationship you guys have right now, if it’s one where you both have asked and failed several times, and yet it’s still considered open to escalate things to some level of romantic intensity of some sort…
Yeah, I’ve yet to see the first “should I send this?” thread where the answer is “yes”-- whether it’s to an old flame, potential new squeeze, co-worker/boss, President of the United States… or all of the above.
What does this mean, exactly? You’ve literally said to her (for example) “let’s go out this Saturday night” and it doesn’t happen? Does she refuse your offers? Do you flake out and cancel?
Yeah, I don’t get it. You’ve asked her out over a *dozen *times? And you want to do it again? You some sort of glutton for punishment, son?
I just want to make sure I understand this: You “just want to talk to her” after she’s (presumably) turned down your advances over a *dozen *times?
Gut advice is to put her out of your mind unless you want a girl to be very pissed off at you for repeatedly not taking a hint.
Secondary advice, if you don’t like the primary advice, is to call her and see if she wants to get drinks. *Writing *her a message will do nothing to show here that you’re not insecure. It’s the coward’s way out. And I say that as someone who took the coward’s way out more than once in my single days. You say every time she saw you she told you to call her? So nut up and do it.
I’m just not understanding what the hell is going on between you two-- you say she tells you to call her, you also say you’ve asked her out over a dozen times and failed every time. Maybe you should scratch my secondary advice and stick with the primary advice above. I wish someone had given me this advice a couple times in my 20s.