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Discussion Starter #1 (Edited)
Okay so this is kinda a long story, but I'm gonna cut it down for you guys.

I've been friends with this guy for about 3 years now... at the time he was one of my good friend's boyfriend (on and off) for years. I became even better friends with him than I was with her. We'll call him B and my friend S. >.<

Anyway. So I had always kinda liked B, but since he was dating S I didn't let on that I did and was just great friends with both of them. Okay so skip to this year. S broke up with B while he was in Jamaica on vacation. All over text. She had talked to me about it before hand. And while I told her that was a really lame way to end a really long relationship, it was ultimately her decision. B had been complaining for about a year now about S, and how they just weren't right for each other anymore. But it still hurt him the way she did it.

Fast forward about 6 months.

I'm still friends with both of them. I hang out with them separately though most of the time, except at parties where obviously everyone's gonna be there. They're totally over it, have no problem hanging out with each other.

Remember how I said I always liked B? Well... I still do. And he definitely likes me as well. We get along really great, and we're pretty much texting 24 hours a day (ugh I know I'm one of those annoying people who's always texting) and he's very obvious about it. There's a problem though. I'm 18, and he's 25. (S is 23.) I've always hung out with older people, I really only have a few friends my own age, so it's not an awkward thing for ME. But he's my best friend's older brother's friend since high school. I don't think I've explained this very well, but her older brother is like an older brother to me, because I pretty much live at my friend's house. (Family issues.)

I don't think he'd ever ask me out under these circumstances. The fact that I'm really good friends with his ex, how weird it would be for our friends to deal with it, etc. However, I'm going away to college this upcoming year (after I graduate), and he's most likely going to be moving to the same city. S is going to be traveling for a year or so, so she's out of the picture. B and I might even have some of the same classes together, because he didn't finish school the first time.

I know I'm horrible at explaining things, and I've created a completely jumbled story for you guys to decipher, ha ha. I'm sorry for that. Right now I'm just playing it by ear. Not really changing anything about myself, or my friendships. I'm hopeful that he will be able to move, and that maybe it wouldn't be so weird.

I do have to be honest and say that one of the reasons S broke up with B was because she hated how much time he spent with me, and how we were always texting. For a while after they broke up she was really ****y towards me, even though I didn't do anything... She has since gotten over it. But still. B even brought it up once, because I was talking to him about how grumpy she'd been lately.

I've probably made B out to sound like a bum. But really, he's one of my best friends. I can tell him everything, and we really mesh well together. He's a very nice guy, works as a mechanic and shows old restored cars with his company, and is going back to school to do more with his life. I've never actually told him how I feel because I'm just not that kind of girl. But I'm very confident that he feels the same way.

Ack, not sure what I'm asking from you guys. Maybe advice? Or someone else in an awkward situation?

I hate posting these girly things, ha ha.
 

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Coming from a girl I know how that is. I have had a friend like an old boyfriend of mine and well shes my best-friend of course I didn't care because well a) me and him didn't last longer then a month and 2)I just didn't care but because these two were on/off a long time you may want to have a talk over with your friend about it to see if its okay with her? Because I wouldn't do something behind a good friends back, because it could get back to her if yall started dating.
Another because your 18 and hes 25 I see no problem your at the age that he can date without it being illegal. So yall wouldn't need to worry there. Anyways if you like him tell him thats the best way and if you want to date him then date him no harm in not dating him.

I am saying this because I know what I am talking about been/ there done that kinda thing :) Been with a lot of guys. and well I am with someone who I know that we mesh well together i can tell him anything we always liked eachother that kinda thing and guess what? Were together. :) and its great,anyways good luck I hope you two end up together.
 

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Discussion Starter #3
Thanks for responding. :] It's not like we'd keep it secret if we dated, and she's already moved on and slept with another guy... more than a few times, although they're not dating because he lives in NY and she's in FL. (I'm not judging, she really likes the guy and he really likes her.) And after she travels she's planning on going to school in New York or somewhere up north. Blah, it's such a complicated mess.
 

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Discussion Starter #4
On a much less angsty note, he got me a really pretty ring for Christmas.
:]
 
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