Best Approach for Asking Long Time Friend Out...???

[Chew_Bear]

First post here.

 

I have ALWAYS liked and wanted to pursue this girl ever since high school. The other thing is...I think she has ALWAYS known it and I think she has always liked me too. In essence...you could say we could have been 'high school sweethearts'.

 

Well...I just had a BIG EPIPHANY about her.

 

The big reason for the big epiphany...

 

I feel I have grown 'old' now and not as confident and 'in my prime' as I have been a few years ago. I don't feel as confident in my looks, game and self esteem any more.

 

I feel 'kinda desperate' because she still looks so good, beautiful and pretty. She's such a strong woman and I feel she would be a great partner for me.

 

Basically...I feel like I am going to LOSE HER if I don't do something now. I don't want to wait any longer. Or worse yet...lose her to someone else and have the biggest REGRET OF MY LIFE.

 

So...What should I do...?

 

There are only 2 scenarios/plans that I can think of.

 

A) Call her and schedule a meeting/date and confess my feelings.

 

B) Call her and schedule a meeting/date but...DO NOT CONFESS FEELINGS. Instead, see where this first meeting/date leads to (i.e. 2nd, 3rd ,4th date etc).

 

I honestly feel I have waited too long and I am really AFRAID of losing this girl FOREVER. I feel I should go with option A as it would have more emphasis/impact and really get my feelings off my chest and across to her more directly.

 

On the other hand...I feel option A is too 'desperate' and 'clingy'. I don't want to come off desperate and clingy. Also...I don't want to jeopardize the friendship and make it 'awkward'.

 

But...I have to do something. And I feel I have to do it soon, as its now or never.

 

Help...?!?!?!

[d0nnivain]

Because HS was part of this equation I'm assuming you are relatively young so I don't understand where this bout of insecurity is coming from. Most people grow more confident over time, not less. What's up with that?

 

As for changing the nature of your relationship with an old friend if you hope to keep the friendship in tact you need to move cautiously. Normally I'm all for the direct approach so you get a straight answer & can move on if it's no. But here, that destroys the friendship & you don't want things to get weird.

 

Step 1 is spend more time with her. Don't talk about the change you want. Just be there. Kind of like your plan B.

 

If you sense there is interest, casually touch her to gauge her reaction. If you can manage to arrange a scenario where you can dance with her in your arms, do that. Does she behave like a woman who is interested or is she keeping you arm's length like you're at a 7th grade dance in Catholic school with a nun next to you?

 

If the dancing was positive, either try to kiss her (you can play that off as an honest mistake if you do it right) or subtly bring the conversation around to whether she ever thought about changing the nature of your relationship. Talk about how love is friendship that caught fire.

 

Only after you confirm that she is as fully committed to trying a romance do you plan an actual date labeled as such.

[Chew_Bear]

Young...?!?!? Haha LOL. Depends on what your definition of young is.

 

I am 33 about to hit 34 yrs old. If my calculations are correct...my High School years were more than 15 years ago. To me...that's kind of old.

 

Is 15 years too long to finally approach this woman...? Should I have done it sooner...?

 

My main concern is...

 

I think she is definitely the 'mommy/family' type and does not want to be single that much longer or have fun going out with friends that much. She has 5 other sisters and 2 of them already have kids.

 

Also...I kind of feel like her feelings and attraction for me is kind of 'waning' and is not as 'strong' as it used to be. I feel if I wait too long, she will lose attraction and interest in me all together. I have seen her with one other guy once and it kind of shot my confidence down a bit.

 

I am afraid that if I wait too long...She will end up marrying/having kids with someone else.

Edited May 25, 2017 by Chew_Bear

[d0nnivain]

OK. Since you are mid 30s cut to find a way to dance with her & ask her if she has ever thought about you two as a couple. If she says yes, say you'd like to try & ask her out. If she is not enthusiastic about the idea, go back to your regularly scheduled friendship. She should be mature enough not to balk too much at your aborted attempt to change the nature of your relationship.

[preraph]

Don't confess anything or talk about it. Just ask her out! Call her on the phone and say, "Pam, I want to go see (movie) this weekend. Would you like to go?"

[Chew_Bear]

Also forgot to mention...

 

This girl's dad died a few years ago and its mostly just her, her mom and a couple sisters that's left.

 

Out of all the sisters, this girl had the closest relationship to her father. They were inseparable and were really good friends. She's also pretty close to her mom as they almost always do everything together.

 

The mom is getting really old too and I think she really wants to take care of her mom.

 

Basically...I can tell that 'time' is ticking away for this girl and I think she really wants to get married and have kids...SOON.

 

At the very least...I just want to have a chance at dating her for a while before she makes a life changing decision that could change both our lives forever.

[Chew_Bear]

On a side note...

 

What would be a good first date with this girl...?

 

I feel like dinner and a movie would be too cliche and boring. I feel that I would have to step it up a notch if I really want to impress this girl and get her to really like me.

 

Any suggestions/advice...?

[preraph]

You're overthinking everything, already making excuses for her, overthinking the date.

 

You should stick to a cliche date so she knows it's a date! Otherwise, she may think it's you just hanging as a friend and go along and waste your time when you're already in the friend zone. Ask her on a date, even use the word "date" if you can. Do ask her to dinner or a movie, or dinner with coffee afterwards or a drink, and make sure she knows it's a date so she can either accept or refuse.

[jjgitties]

Hate to break it to you. But once you have been friend zoned by a woman, you never get out of it. But there is no harm in trying. You just got to try to do it smart so you don't lose a friend. You see what happens is. If you make a move and she does no recipricate , it's gonna get awkward. That's where the friendship might die.