Thank God for anonymity...

Ronin74

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... because I never thought I'd ask a question like this. After who-knows-how-many (maybe lamost 10) years of sitting by the sidelines, I decided to take a shot at reconnecting with an old friend, and yes, with the intention of possibly dating her. The problems (or at least two of them) are:
  1. Is it possible to be so out-of-league with her that perhaps the shot isn't worth taking? She's been married (which was the last time we spoke) and divorced, and had a fairly successful career, whereas I sort of disappeared; turned her down when she first hinted an interest; and kind of let my life fall apart.
  2. If it is worth taking, how do I start off?
I know this is about as unrelated to MT or MA as it can get, but I feel like I'm at an impasse before even trying, so any advice would probably be appreciated.
 
Nothing ventured, nothing gained.

But I'd suggest starting by simply getting back in touch and seeing what's up, with no more pressure than that. She may be remarried, dating, or have become a nun. Why add extra freight till you know where things stand? Instead, keep it at reconnecting with an old friend and renewing that friendship.
 
What is there to lose?

Downside she says no, you suffer a bump to your ego, upside you wind up with a girl who you apparently think is out of your league.

Pretty much a no-brainer in my book.
 
Nothing ventured, nothing gained.

But I'd suggest starting by simply getting back in touch and seeing what's up, with no more pressure than that. She may be remarried, dating, or have become a nun. Why add extra freight till you know where things stand? Instead, keep it at reconnecting with an old friend and renewing that friendship.
Makes sense, however there's a few details I'm a little unsure about. Like I said, it's been sometime since we've kept in touch- and it was a long-distance communication- and in that time she's changed her # and email address.

Plus in the time we've been out of touch, her career's taken off somewhat, and met quite a few people, which leaves a slight chance she might've forgotten about me. So in a sense, it's almost like starting from scratch at half the strength. Am I making sense on that one?
 
What is there to lose?

Downside she says no, you suffer a bump to your ego, upside you wind up with a girl who you apparently think is out of your league.

Pretty much a no-brainer in my book.
True, just a bump to the ego, but how to start is a major question.
 
The first step is to find her. Sounds like all her contact info has changed. If you find her, ask her out, be honest about your life and and let the chips fall. For all you know she may be thinking about you right now.
 
You might try facebook . . . if you can't find her, then find friends of hers and connect through them.

Then, if she accepts your friends request, she remembers you, if not, there ya go.

(That's if she has a facebook page, but you'd be surprised how many professionals are using it now.)
 
You might try facebook . . . if you can't find her, then find friends of hers and connect through them.

Then, if she accepts your friends request, she remembers you, if not, there ya go.

(That's if she has a facebook page, but you'd be surprised how many professionals are using it now.)
LOL... I've been ignoring requests to join facebook, but I guess now I have a reason.
 
LOL... I've been ignoring requests to join facebook, but I guess now I have a reason.

I avoided it for a long time, too, but it's a lot more "grown up" than myspace. Plus, it "requires" you to use your real name, so people are easier to find.
 
I avoided it for a long time, too, but it's a lot more "grown up" than myspace. Plus, it "requires" you to use your real name, so people are easier to find.
Oh wow! I think I just found her. I'm crossing my fingers that she might remember me.

Quick Update:
There's two profiles using the same photo, and several without photos. :(
 
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I'm suddenly up to 20 friends, but she's not one of them.
 
Most important at such a stage, i think is to evaluate your own wishes and find out whether you can commit. Then the very important other point is to really balance out if the person in question fits well to you. Know her downsides and be able to love them too. For example, if she spaz all the time and freak out, you gotsta be able to take that **** for years and accept it somehow understanding.
If you are really are great friends and very suitable for one another, it would be a shame not trying. Are there kids on any sides? If so that might also make it a bigger responsiblity. Reason i say this is 'cause i can relate to what you said and i take it, you don't what to play musical chairs with partners forever. There comes a time where one wants to settle down. Find a partner that it is enjoyable living life with. Together one is stronger than alone.


j
 
Most important at such a stage, i think is to evaluate your own wishes and find out whether you can commit. Then the very important other point is to really balance out if the person in question fits well to you. Know her downsides and be able to love them too. For example, if she spaz all the time and freak out, you gotsta be able to take that **** for years and accept it somehow understanding.
If you are really are great friends and very suitable for one another, it would be a shame not trying. Are there kids on any sides? If so that might also make it a bigger responsiblity. Reason i say this is 'cause i can relate to what you said and i take it, you don't what to play musical chairs with partners forever. There comes a time where one wants to settle down. Find a partner that it is enjoyable living life with. Together one is stronger than alone.


j
True. Evaluating the initial pros and cons, as well as estimating strengths, weaknesses and resources is the deciding factor over whether I should go through with this endeavor. However, I still need to be establish some line of communication to get a clear and acurate picture of the scenario.
 
Know who is deciding that the girl is out of your league? You are! Why not reverse the thinking and make the you out of HER league? That'll attract her and make her pursue YOU.
 
Give me her contact info, I'll make sure that I mention you.
 
True. Evaluating the initial pros and cons, as well as estimating strengths, weaknesses and resources is the deciding factor over whether I should go through with this endeavor. However, I still need to be establish some line of communication to get a clear and acurate picture of the scenario.

Overanalyze much?

Email, write a bit about yourself, if she rights back and is friendly get her number. Call her, and see where it goes. At some point in life you have to take a risk, relationships are one of them, if you can't take the risk of even starting one, good luck maintaining one.
 
Keep in mind that anonymity goes both ways, so you're going to get a lot of advice from people who won't be bearing the cost of heeding it. ;)
 
Overanalyze much?

Nope, that's just my thought process stretched out.

Email, write a bit about yourself, if she rights back and is friendly get her number. Call her, and see where it goes. At some point in life you have to take a risk, relationships are one of them, if you can't take the risk of even starting one, good luck maintaining one.

That's still part pof the communication issue. I believe I mentioned that her contact info has changed, so reluctantly, I'm trying the facebook route.
 
That's still part pof the communication issue. I believe I mentioned that her contact info has changed, so reluctantly, I'm trying the facebook route.

Facebook has a wall to wall feature where messages can be private, its alot like an email.
 
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