I had a "boyfriend" from 6th to the 8th grade (really we were just buddies). We've stayed friends throughout the years and I've come to rely on him as one of my best friends. He and I have always been there for each other: from practical stuff down to breakups and traumas. We get along really well and I enjoy having him in my life.

Over the last two-three years, he has strongly expressed deeper/romantic feelings for me. In 2009, I dated him for about two weeks but I just didn't feel *it*. I have tried expressing to him my regret for leading him on, and that I value him so much as a friend and important person in my life. I always thought we would be okay, but he stayed pretty adamant that I just needed to grow up a little and eventually I would see that we were meant to be.

In Fall 2010, I tried my best to explain to him that he was a very important person to me, and it would be wonderful for us to be a part of each other's lives, but he needed to understand that nothing romantic would ever happen.

I guess I finally got the message across to him, but now he's cold. He has a new girlfriend, which is great, but when I ask him how they are doing he writes "She's amazing, she really gets me and isn't afraid to love me. She accepts me for who I am, faults and all. She's a grown up which is what I should have been looking for all along."

I get it, he's bitter at me. My question is: is our friendship a lost cause? I keep trying to make plans for double dates, or game nights, or just email him-but all I'm getting in return are short, cold emails or he's flat out ignoring me. I hate the idea of losing him as a friend-but maybe leaving him alone for good is the best thing I can do for him? Any insight is great.

(I know I ask a ton of questions here about emotional stuff--thank you all for your advice, support, and insights. And patience!)

If you value the friendship I'd keep it casual. For whatever reason he feels the need to get back at you by telling you how amazing his NEW girlfriend is, how adult she is - slap, slap, slap at you.

I'd be casual and not pester him.

I wouldn't make plans or try to make plans involving him. He's already made it pretty clear that he's not interested.

I never think a rift in a friendship is a lost cause if BOTH of you value the friendship. The fact that he hasn't closed the door indicates to me he either wants to leave that door open because he's hoping you can have a relationship OR he wants to resume the friendship.

My concern in all of this is the new girlfriend - and I appreciate you're not the old girlfriend. I can't imagine how she feels and I would go W-A-A-Y out of my way to keep from hurting her.

He's using her to get at you - unfair to both of you.

You're absolutely right. If he wants to resume the friendship, I'm always here. I should stop pestering him, however.

I want him to be happy and loved, and if me being merely a peripheral part of his life is the way for that to happen, then it's worth it to me.

I have no romantic ambitions toward him, but there's no way for his girlfriend to know that. I hope that he has more intentions for her than using her as a tool to hurt my feelings, because as you said that would be very unfair to her. My fingers are crossed that with her or with someone else, he finds someone to truly care about and who truly cares about him.

Thanks, Judy! :)

The best we can wish for "ex's" or almost "ex's" or might have been "ex's" is that they find happiness. Sounds like he's got to get it out of his system and then, hopefully, he finds his destiny.