Ok, I'll keep this as short as possible.

I dated this girl in high school for a very short time. Probably about a month. I really liked her. She was beautiful and really sweet. Hottest girl I ever dated. I may have even been the first guy she kissed... but not sure. The problem with her was she never talked because she was really shy and introverted. So I pretty much stopped going out with her because she wouldn't ever talk to me - it drove me nuts.

Flash forward like 7 or 8 years. After my ex dumps me, I moved back to the town where I grew up and went to high school. I sign up for Facebook. Out of the blue, this girl is one of the first to write on my Wall. We send some messages back and forth. Turns out after high school she went to college, joined a sorority, and is now really outgoing and fun. I get her Gmail name and we chatted every now and then online while at work. I kept busting her balls because we made plans to grab a beer, but it never really happened. Then around Christmas time we did go out for that beer. She texted me after about a week of not talking to her and asked if I wanted to meet up. We ended up hanging about for about 3 hours or so... she still the same old girl but now way hotter and way more outgoing. Somehow during the conversation she tells me that she likes to date left-handed, creative people who are into art and music. DING DING DING. That's me. Plus, I already dated her once, so I know she liked me at one point...

Anyway, hanging out with her brought up memories, and made me kind of start to like her again. Of course, I find out she has a boyfriend she's been dating for a year and some change, so I didn't really push my luck, and stopped talking to her all the time. Every now and then we still chat online, but I haven't seen her or hung out with her since Christmas.

Present day - I sign onto Facebook and see that she's broken up with her boyfriend a few days ago. I see my opportunity to try my luck again here. I just don't know how to approach it though. If I start suddenly talking to her a lot more, she'll know that it's just because she broke up with her boyfriend. Also, I don't want to be her buddy and her shoulder to cry on, etc. because all that will do is slap me right into the Friend Zone. I'm also aware that her breakup is fresh and the wounds are still open, so I don't want to come across as an insensitive @$$. Anyone have ANY idea how to approach this girl in such a way that I don't come across as simply hitting on her because she's now single? I guess my goal is to come across as caring and kind (which I am, I do care about her) but also as a potential future boyfriend. In other words, I have to indicate my interest in her in some way, without being blatant about it, but also seem like someone she can trust and confide in without coming across as 'just a friend.'

Not to mention the whole rebound factor... don't want to rush because if I am successful I don't want to be the rebound guy... but I don't want to wait too long to try and get her interested, else someone might beat me to it.

POINTERS PLEASE! :D You guys are the best...

You say you haven't seen her since Christmas... but have chatted online every once in awhile... when was the last time you chatted with her? Wait a week and then chat with her again. You never know... she may call you before you try to contact her. She probably is in rebound mode... but that doesn't mean that you will be categorized as FRIEND. You do have a high percentage of this turning into what you want... just give it a little time.

Be honest with her and express everything that you just said directly to her. You know each other and she is comfortable with you. Let her know your interested and when she's ready you'd like to date her more seriously. How do you know you are not the reason why she broke things off with the boyfriend. Don't play too coy, you might give off the wrong impression. Honesty is truly the best policy... you'll see.

You DO want to be her buddy.
It doesn't matter if she thinks you're hanging with her now because she is available. It's true, isn't it?
You DO want to be a shoulder for her to cry on.
You DO want to be her friend first. In fact it's WAY more important than anything right now.
You don't have to "present" yourself as a suitor. Just start being with her.
Be an awesome, interesting, caring, available man wiith a life and interests of his own and time to share with her
When she's done crying over her ex, you're already THERE at her side being awesome.

If you want things to go better this time, don't treat her like you do all other dating goals. Be there for her on all levels. Don't worry about her being there for you yet. That's not the point. Be a rock FOR her. Be security FOR her.

Treat her selflessly the way you hope she'll treat you back when she's ready. Whether she does or not, you keep doing it... and having a full life at the same time. Very attractive "potential mate" picture you paint without having to be a pursuer.

Good luck.

JB said it all and said it well.

Be yourself, be cool. For now, just be there for her and be patient.

Good luck, and keep us posted.

http://smileys.smileycentral.com/cat/15/15_11_2.gif (http://www.smileycentral.com/?partner=ZSzeb001_ZSYYYYYYMXDE)Food for thought - don't expect too much and be surprised at the outcome, or expect too much and be ready for a fall.

Hey freakingconfused:

Take JB's advice! Let us know how it goes, seems like this is an exciting start to something great!

You say you haven't seen her since Christmas...but have chatted online every once in awhile...when was the last time you chatted with her??

Probably two or three weeks ago. Highly doubt she'll randomly call me up, but you're right, you never know. She did randomly text me and ask me out for a drink one day, but that was only after I tried to meet up with her for a beer a time or two. Might have just been because she felt bad we never met up, or maybe she thought I'd leave her alone after that. Or maybe she just wanted to see how I was after all these years. Who knows!


You do have a high percentage of this turning into what you want...just give it a little time. That's my biggest problem - got to be patient. Thanks for the advice!

Be honest with her and express everything that you just said directly to her. You know each other and she is comfortable with you. Let her know your interested and when she's ready you'd like to date her more seriously. Yes, we do know each other... but the "me" she knows is from like 8 years ago, when we dated for a month or so. We're both different people now, but are still the same in some respects, and we don't know each other that well anymore. To me though, coming right out and saying something like this seems kind of... cheesy? I don't feel like I should just plop that right out on the table, especially if she is fresh out of a breakup. Seems kind of selfish or something. I need to be more indirect about it, but somehow still get the message across. Plus, I don't know if she even remotely feels the same way about me... and that's probably the last thing on her mind right now.


How do you know you are not the reason why she broke things off with the boyfriend. Wish that were the reason! I can't rule it out, but really, I don't think so. There's no signs or behavior from her to think that would be the reason. The reason is her ex, from what I can tell, is a giant douche bag... but I really don't know the reason they broke up.

I do have to enjoy young love, not calling for this reason or that, looking them up on myspace or Facebook and don't even get me started on texting. You pick up the phone and call and talk to people you like, if you wait too long it will be new boyfriend being talked about and it will not be you.

Me, I call her. Go slow, but go!

Me, I call her. Go slow, but go!!

I agree (had to spread it again).

You seem to spend a lot of time second-guessing her motives. There are too many 'maybe she... ' You'll never know just thinking and not acting. So get on the horn and invite her for lunch or ice-cream, have a neutral conversation and watch her eyes and other movements. Face-to-face communication is the key to unlock those questions here, NOT what ifs.

If she shows no interest at the present time you'll at least be more informed than you are now and can go on with your life.

Again, good luck.

http://smileys.smileycentral.com/cat/15/15_11_2.gif (http://www.smileycentral.com/?partner=ZSzeb001_ZSYYYYYYMXDE)

Probably two or three weeks ago. Highly doubt she'll randomly call me up, but you're right, ya never know. She did randomly text me and ask me out for a drink one day, but that was only after I tried to meet up with her for a beer a time or two. Might have just been because she felt bad we never met up, or maybe she thought I'd leave her alone after that. Or maybe she just wanted to see how I was after all these years. Who knows!

That's my biggest problem - gotta be patient. Thanks for the advice!

You're very welcome! Hope things work out! You should definitely be a friend and support her... she'll appreciate it.

Wait a little bit longer before contacting her, a week or so will probably do. Then write on her wall saying something along the lines of "long time no see! How've you been doing?"