Setting myself up to get hurt

Caution: long personal post ahead.

I’m beginning to fall for my best friend. I’ve been in similar situations before, where I’ve been good friends with a girl, then that becomes something more. For me anyway. This sort of beginning hasn’t resulted in an actual relationship yet. On the other hand, it’s never resulted in anything I regret either.

We met at work two years ago, and flirted and sort of went out a couple of times. If I hadn’t been so afraid to try anything, we would probably have progressed further. She told me once, not so long ago that she never did know why it was I didn’t try anything back then. Live and learn.

But that was two years ago. After that summer, she went back to Princeton, and I stayed in Houston. We started corresponding by email and AIM. We even gave each other birthday and Christmas presents, and met again during the winter break.

Then I started going out with my now ex-girlfriend. And for a year, I was happy with just being friends, corresponding again by email and AIM. Then of course, my ex dumped me and Cath was there to help me through it. Some of you met her about then. She joined me for a doper get together early this year. So from then our friendship grew. We talked almost every day, usually for several hours. But of course, she was in New Jersey, and I was in Houston, and I didn’t know where I’d be come graduation. Now I do.

By fortuitous coincidence, we’ve both ended up in Austin. Living in the same apartment complex no less (she found it, but it was the best one for me too). I’ve found myself thinking more and more about her lately, as more than just a friend. But I don’t think she’s thinking of me in the same way.

I’m setting myself up to get hurt. I know the smartest thing to do would be to just toss all of these thoughts out the window and let things develop on their own if they will. But my mind keeps racing ahead of reality. Fortunately, I know myself well enough that I know that this isn’t going to ruin our friendship. I can take no for an answer, I just need to be reminded of it occasionally.

On the other hand, maybe this will all work out. We’ve spent countless hours telling each other the details of our lives, our hopes and fears, and all those other intimate details. I know that she was attracted to me at one time and I blew it. Do second chances come around?

Sigh. It’s odd. My first inclination is to go talk to her about all of this. She’s my best friend, who better to share with? But I don’t want to put any pressure or do anything stupid. I want things to develop as they will. Then again, she knows of the existence of this board, and she knows my user name. Maybe I’m just hoping she’ll find this herself.

I don’t quite know why I posted this, except that I needed to get it off my chest, and I can’t talk to her about it. I’m not looking for advice, but you can provide some anyway, if you have any. Or you can just slap me upside the head for being so stupid.

I had to consider for a moment whether to even try to respond to this; well, here we go…

Been there, done that, multiple times (I seem to have a lot of female friends) as you say you have.

I’m going to try to be simple so I don’t get lost, pal. You’ve got to, basically, make a pass at her. She may well never “get the idea” and you can watch whatever develop into her meeting another guy and it being the thing of her life while you play the friend. I’m not kidding about the been there done that part.

Now, by a pass, I don’t mean anything sexually suggestive. That’s a pass you use at the bars for a weekend’s merriment. My humble brain comes up with something along the lines of, at opportune moment, a mild touch and a statement along the lines of, “I really like you,” or some such. Perhaps with some luck our pass style mavens will drop in and give you some finer points than I could never provide.

The post to a mutually known board isn’t likely going to provide nucleation. I remember meeting her, seems like a great gal. But you’re going to have to pull the trigger, pal.

Good luck!

OK. <slap> Ya putz! Are you gonna make a move or not?

Seriously, I think you’ve got the makings of something great here. Most of the best relationships I’ve ever known (my own included) started as “just friends”. Then again, she might not be interested, and if not it might be awkward for a while–but if your friendship is that strong, you’ll get through it.

My point is that you have everything to gain by throwing your cards on the table, and not much to lose by holding back. Do it now. Now, I say!

Dr. J

Oh, I know that I’ve got to be the one to initiate, I’ve experienced the consequences of standing by. I didn’t (and still don’t) expect her to find this, and that’d be a pretty wimpy way of going about it anyway.

She’s not actually moved in here yet, and when she does, she’ll be working even longer hours than I do. But I still expect to spend quite a bit of time with her. That first unmistakable pass is the difficult part. I will do it (provided she doesn’t send me signals to the contrary), but the how and when eludes me for now. Maybe I’ll just remind her that she (jokingly) made me promise to give her a massage. :slight_smile: Heck, that’s why I bought the oil. More likely I’ll try something like you suggested, over dinner.

It’s going to hurt if she doesn’t want to give me a chance, but that possibility alone isn’t going to scare me off. I learned my guiding rule in one of those previous friendships: Do what I’d regret not doing, and don’t do what I would regret doing.

I like that.

I’ve been there too, TheNerd (I don’t wanna just call you “Nerd,” since it looks like an insult), and I agree with the prevailing sentiment–you gotta go for it. I myself have never had a relationship with a woman that didn’t begin with being friends–I don’t think I’d even want any other kind.

There’s a country song about this very subject–I don’t remember who does it, but I think it’s called What If I Said–that goes approximately:

“Do we dare to cross that line
between your heart and mine?
Would I lose a friend,
or find a love that never ends?”

You might get hurt…but then again, it might be the best move you ever made.

Good luck.

Okay, TheNerd, from a female point of view: Go for it…just make sure you’re willing to risk the friendship if she is put off by your approach. (She’ll probably be flattered, if nothing else.) I’ll tell you what would have worked on me: touch her hair. Brush it back from her face or just touch it lightly…then tell her you really like her. Then let her respond. Go from there. If she says “just friends” then take her at her word…for now. She may re-evaluate, now that you’ve put the idea in her head…