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In (probably) unrequited love with my best friend

Tagged as: Dating, Troubled relationships<< Previous question   Next question >>
Question - (25 April 2009) 1 Answers - (Newest, 27 April 2009)
A female United States age 41-50, anonymous writes:

I have a very good friend, let's call him John. I've known John for many years now, I met him through his sister (let's call her Kate) who I was my roommate in college. Over the past few years, he and I have gotten very close. He tells me nearly everything, and I feel very comfortable with him too. After a long night out, our favorite pass-time is curling up in each other's arms and falling asleep. We hug and cuddle a lot, and he's constantly calling me just to check in, and see when we can meet up next.

John is a very good looking man, and women tend to appreciate him. He's actually quite awkward with women, but we tend to find that trait rather adorable in him. I've seen him work his way through most of his sister Kate's friends (with only 1 exception not including myself). He starts every liaison with great intentions, and really excited about a new prospect, and promptly ends it when it's becoming clear that the girl wants more attention from him than he's willing to give. I personally believe that he's still in love with his ex from about 6 years ago, and every woman since has lost in the comparison.

About 2 years ago, I introduced him to my sister (8 years younger than John) and he developed an unrequited crush. My sister (who is a VERY beautiful actress) was actually a bit creeped out by him. And John now gets very awkward when he's forced to interact with her. (or even when I bring her up in conversation)

My feelings for him are very complicated, but for all intents and purposes, they have grown into love within the past year or so. My sister and I are both very alike and very different. (she's much hotter and while she is younger, she's used to male attention, I am NOT)

One other anecdote: A while back, his brother's girlfriend asked whether or not we were dating, I babbled, and basically declared that John's track record with women rendered him "undatable" to me. (i don't know WHAT i was thinking) John got very upset and we had our first fight a few days later on this topic. He was upset (ego bruised) and hurt by what I said, and he said that it seems that I think that he's constantly hitting on me, which I DON'T.

#1) I'm sick of having my male friends (and men in general really) invariably prefer my sister to me, I'm not really jealous of her per se, I'm just tired of unfavorable comparisons. While I love John, I don't really care to be a consolation prize.

#2) I also don't want to be just another one of Kate's friends that he dates. Our current friendship is too important to me. I know that if something was going to happen between the two of us, it would have happened by now.

SOOO...

my question is, a) am i being too pessimistic? should I just wait and see if he will eventually return my (somewhat well concealed) feelings? or more likely, b) i really AM only ever going to be a friend to him, in which case, how do I get over this and stay his friend, because I can't lose that.

View related questions: best friend, crush, his ex, jealous, roommate

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A male reader, Who United States +, writes (27 April 2009):

Who agony aunt“I also don't want to be just another one of Kate's friends that he dates….I'm not really jealous of her per se, I'm just tired of unfavorable comparisons. While I love John, I don't really care to be a consolation prize.”

I would say it would be best to get beyond these ideas. With John you either have a friendship, a relationship, or nothing. It’s between you and him; no other woman affects your situation.

“am i being too pessimistic? should I just wait and see if he will eventually return my (somewhat well concealed) feelings?”

On their death beds, most people regret the things they didn’t do rather than the things they tried that didn’t work out. They wonder about the relationships they didn’t have, not the friendships they lost.

Have you been through a few relationships, and had you heartbroken a few times? Had you had to tell a boy friend or two it was over? Do you now know what you want in a relationship and from a man? Is it John? If so, close your eyes and jump.

“I just wait and see if he will eventually return my (somewhat well concealed) feelings?”

I’m guessing at this point waiting will mean nothing will happen; you are going to have to make it happen. You are going to have to get him thinking about you the way you think about him. Maybe try saying “So you don’t like that I said you are "undatable" to me? I’ll give you the opportunity to prove I’m wrong. If you ask me out I will say yes.” Say this and let him think about it for a bit. Most men have to think for a while before deciding to peruse a woman.

“I personally believe that he's still in love with his ex from about 6 years ago, and every woman since has lost in the comparison.”

If you are correct, maybe the way for you to escape the comparison trap is to say “You know the things you had with [the ex] that you miss? I bet if you work at it a bit you could have those things with me.” Don’t say this until you have been out on a few romantic dates (not friendship dates.) And again say this when you can step back and let him think about it. You don’t want to debate him on whether it is true or not, or give him the opportunity to say “you don’t know what [the ex] and I had!” Don’t throw yourself at him, but get him thinking about what he can have with you if he makes the effort.

“b) i really AM only ever going to be a friend to him, in which case, how do I get over this and stay his friend, because I can't lose that.”

Staying his friend is the low risk option. If you take it the way you get over your current feelings (beyond friendship) is find another man who makes you feel those feelings with him, and make you forget that you ever had them with anyone else.

Good luck and I hope this helps.

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