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My best friend: to date or not to date?

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (26 July 2010) 4 Answers - (Newest, 27 July 2010)
A male United States age 30-35, *anAfterChrist writes:

So I posted this question but got no answers. So here it is again.

Hey y'all. Sorry I haven't been giving advice too much lately, I just haven't been online too much this summer.

Anyways, I'm having a little emotional dilemma.

My best friend is a woman. Our relationship is closer than any relationship I've ever had before, male or female. We've pretty much always maintained that we would never date; we were too close of friends and just didn't see each other that way. I maintained that attitude amongst our friends and families, and believed that I had no romantic feelings for her for a long time.

Well, some mutual friends have really started pushing me to date her. It's NOT one of those "Hey, she told me she liked you so here's the hint" type things. It's more of a "She's had a lot of bad guys, we all know you two would be perfect together. Date." type situation. And the more I was confronted with it, the more I asked myself how I felt about it. The more I thought about it... well, the more I realized I had honestly been suppressing some romantic feelings towards my friend.

I've been told by countless people that a man cannot be JUST friends with a woman. I never believed it. But now, I'm starting to believe the Dave Matthews quote: "A guy and a girl can be just friends, but at one point or another, they will fall for each other...Maybe temporarily, maybe at the wrong time, maybe too late, or maybe forever”.

I don't want to ruin anything. But I also don't want to be standing there at her wedding wondering "Why did I let this pass by?"

I have absolutely no idea where she stands in this. If I were to wager a guess, I would assume she is totally not interested in anything romantic. I'm about 80% certain that I at least want to talk to her about it. We've always been open with each other, and I'd like to keep it that way. I guess my question has two parts:

1) Do you think my decision is wise to try and date her, even though we have an incredibly deep emotional connection that could potentially be ruined?

2) If yes, and I go for it: If she isn't interested at all, how can I assure her that I will still always be there for her as a friend? And I will maintain pure friendship without my romantic bias getting in the way.

If no, and I don't go for it: How do I make certain that I have no ulterior motive while giving her advice in the future? For example, if she talks about a new potential boyfriend, how can I take out my bias and accurately assess him and the situation?

Thank you for the responses.

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A male reader, ManAfterChrist United States +, writes (27 July 2010):

ManAfterChrist is verified as being by the original poster of the question

ManAfterChrist agony auntThank you Katie. If anything comes out of it, I will update.

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A male reader, ManAfterChrist United States +, writes (26 July 2010):

ManAfterChrist is verified as being by the original poster of the question

ManAfterChrist agony auntHey Paul,

Thanks for the confidence. I guess the bias might always be there, but because I love her I will always act in her best interest. I actually already talked to her today, but it was very mild. I basically just said "I just want you to know, because it's never really been said before, that if the opportunity arose I would date you."

I wanted to tell her more, but it will come in time. We will be friends for a very, very long time. We do love each other, and we both make sure the other knows that in actions and words on a regular basis. So it does sound like you and I are in the same boat.

Wish me luck in the future, and best of luck to you!

P.S. You said you are in the same position, but it also sounds like you are a couple steps ahead of me. What progressions are we seeing?

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A female reader, Katie23 United Kingdom +, writes (26 July 2010):

I'm in a similar situation too, although I have really strong feelings for my close guy friend and am trying to decide whether it's a good idea to risk telling him. So I feel your pain lol!I think deep down you know whether your friendship is strong enough not to be damaged if you tell her and she doesn't feel the same, or if you guys started dating and it didn't work out. If you think you can tell her without it ruining the friendship then go for it, just tread carefully and don't come on too strong with your feelings all at once or you might scare her a bit. I know that if the situation was reversed and my guy friend liked me I would want him to be able to tell me even if I didn't feel the same way. At least then the air is cleared and you both know where you stand. Hope this helps, let us know what happens!

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A male reader, paul739 United Kingdom +, writes (26 July 2010):

I am in the same position. So for what it's worth. Yes I do think you should try to date her. I have had exactly the same thoughts about standing at her wedding to someone else! My conclusion to my own situation is that me and this girl have been best friends for 12 years and the penny dropped that we are best friends for a reason..because we love each other:) If your friendship is as strong as you believe, then this shouldn't destroy it if she is not interested, and who knows putting the thought into her head may give her something to think about. It may get to the stage where regardless of if you have told her your feelings or not those feelings will be there all the same so you will be biased against any other man who comes along and shows an interest in her. Go get her!

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