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I know that I'd like to try dating him one more time. Should I bring it up?

Tagged as: Big Questions, Dating, Friends, Teenage<< Previous question   Next question >>
Question - (27 June 2009) 5 Answers - (Newest, 27 June 2009)
A female United States age 30-35, anonymous writes:

Okay, so I think I realized i'm either a) in love with my best friend or b) in love with our friendship. We've been best friends for about 4 years now. We've dated once for a period of 3 months. Our relationship didn't really go anywhere because both of us were afraid of messing up our strong friendship. We're still the best of friends even after everything happened. We're going to camp soon and I've been thinking about bringing up the subject of "us." We hang out all the time and he's such an amazing guy. The two of us can talk about anything. We get along so well. He's been by my side for everything I've gone through. We went off for lunch to his house several times during the school year. His mom was always there, and we get along really well. She tells me how much she likes me every time I go to his house. I've been thinking about suggesting the idea we try dating one more time. We both have our license now and it makes things so much easier. Before, my parents were the problem. We hang out so much anyways, that my parents shouldn't mind now. He's said he likes us being best friends before. Meaning just friends. He also has a funny way of showing he likes me. Before he asked me out, he went around and denied he liked me to everyone. So I can't tell if he really does like me or not. I just know that I'd really like to try dating him one more time. Should I bring it up?

View related questions: best friend, period

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A female reader, anonymous, writes (27 June 2009):

Thanks I appreciate the responses! To clear things up, while we were both scared of messing up our friendship, my parents seemed like the problem to me. He's Jewish and they don't like that at all. But he never knew any of this, so it was more so of a personal problem for me. So basically I battled that problem on the inside and on the outside both of us were afraid of messing up our friendship. I agree with the person who said it seems like our friendship can't be destroyed. We've dated and things are right back where they were before. We're such good friends it's like we're dating anyways. It doesn't seem like a break up even happened. I think either way I'd still have a best friend. I'm not really worried about losing him. We've agreed that pretty much nothing could break off our friendship because neither of us want that.

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A female reader, anonymous, writes (27 June 2009):

I agree with inlove. The same thing happened to me... and guess what, it ended in both of us not being friends for two years... then I had not lost simply a bf, but I had lost my best friend...

Only if the two of you really feel that you love eachother, more than best friends, and until you know he feels the same way... keep him as your best friend only. Maybe one day you will end up being together, and maybe one day you won't- but you will still most likely have him as your friend. Which is better than not having him at all.

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A female reader, in_love004 United States +, writes (27 June 2009):

i have been in this exact situation and personally speaking i think you should just keep things the way they are. It may seem like both really want to date each other and i can tell how much you care about him which is all the more reason y u shouldnt date him, the more emotions are involved, the more complicated things get and if things go wrong not only will i have lost a boyfriend, but a friend as well, so i say stay friends. and if its mesnt to be, yhen it will be

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A reader, anonymous, writes (27 June 2009):

Well first you said that you were both scared of ruining your strong friendship and then you said "my parents were the problem earlier."

So which is it? Because there's a difference. If your parents truely were the reason you couldn't work your frienship out ot be anything more, then it may be a good idea to bring it up, if that's what your heart is telling you.

But if it was because you didn't want to ruin your friendship, then I think the contrare is true. You've already given it a fair shot and it didn't work, so maybe it's best you stay friends?

The way I see it.. Love is just love.. it's there or it's not. And you two have been such great friends for this long, if there was something romantic there, I think you would've felt it, pursued it and had success with it a lot earlier on.

~Sy.

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A male reader, anonymous, writes (27 June 2009):

Go for it. It sounds like you're really interested in him and things seem like they would work out. Give it a try. I understand your concern for losing a special friendship but if you feel like you want more its worth risking. But it seems like your friendship couldn't really be destroyed anyway. By that I mean your friendship seems strong.

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