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After 25 years, is it worth taking a shot at more?

Published on October 8, 2012 by fesser98sp

So I am a 34 yo, divorced Mom. I have known one of my best friends that I grew up with for 25 years, we met when I was 9. We graduated high school together, but lost touch after I went to college. I got married, kids, forward to 2009. We found each other again on facebook, by then I had moved back near our hometown, and he was living in another state. We talked online, got caught up, occasional phone calls, and when he was in town visiting family we would make plans to get together. He's spent time with me and  my boys and doesn't seem to mind them. (My kids have issues and most adults have a hard time dealing with them.) A couple years ago he decided to move back to this area to be closer to his parents, his Mom has a lot of health issues. I get to see him more often than I did. But I am not sure what to do.

We both have busy schedules kids, family, work, etc. And despite the fact that we basically picked our friendship up right where we left off, something is different. Not bad, just different. Maybe its because we are older now, I don't know. But lately, I keep wondering if maybe it would be a good idea to change our relationship. He's smart, funny, kind, thoughtful, understanding, I trust him, and can talk to him about almost anything. I just don't want to screw it up. But the last couple times we've gotten together, I haven't wanted to leave. I'm not sure if its just that I have been single for so long or what? I want to ask him what he thinks, but I don't want things to get awkward either. He's always seemed to be so content being single, and he has dated but he says never gotten serious about anyone. I just don't know how to figure out if he would be interested or to even bring it up? I don't even know if either of us can even find time to manage anything more complicated than friendship.

So I guess the big question is what should I do? Should I just let it go or should I just blurt it out? Is it worth the risk?


I know I'm new around here but here is my 2 cents anyways. A few months ago I met a man who is amazing. He is kind and funny smarter then I can ever hope to be and just a generally great guy. If I could build the perfect guy he'd be about 12% close to it.

When he told me he was starting to like me I had just gotten out of two annoying and weird online relationships and was not in the mood to deal with another so I said get over it. (As gently as possible) so we remained friends. Now we've been friends for about six months and are building a business together via the internet. I found out a few days ago he got engaged a month ago. Needless to say I wasn't happy and am now kicking myself.

If you think there may be something there go for it. If he turns you down yes it will be awkward for awhile if you allow it to be. Speak to him as an adult see what he says other wise not only will you never know but you'll be the one kicking yourself later.

You can't find out if you don't give it a try. Let him know that you have come to have feelings for him that are growing beyond those of just a long-time friend, ask him if has has any similar feelings, and if he would welcome a romantic relationship with you. I think the risk of losing him is very small (perhaps an awkward moment if he doesn't want to have a romantic relationship, but a good friend won't go running away).

Take a chance - he sounds like a good man.

All right, now I just have to figure out how to approach the subject??? Maybe I should just randomly ask him to marry me out of the blue and see what happens... I don't think just walking up and kissing him would work. Or just trying to straight up talk about it either. It just seems like things would end up really awkward that way, and someone's feelings will end up hurt. We've always had more of a fun loving playful kind of friendship. So what do you guys think? Would proposing be a good ice breaker to bring up the subject without it being too awkward?