Question:

How should I ask my best friend if he's thought of being romantic with me, too?

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How can I start a conversation with my best friend about possibly becoming romantic? I've known him for 20 years now (since we were 7) and everytime he breaks up with someone, my feelings for him return. We're flirty. He is kind of old-fashioned in that he always calls me the day after we hang out to tell me what a good time he had! Last time I saw him, he told me he was going to make me a key to his house. We exchange "I love you"'s all the time. We've never been intimate... never even kissed other than on cheek. My family wants us to be together and his sister wants me as a sister-in-law. The other day, I told him about how my mom said that she wanted me and "Joe" to make her some babies. We laughed. I thought that would start a conversation but it didn't. We have this awesome relationship where we know what the other person is thinking. Almost like ESP with each other. I can't describe it because I have never experienced it with anyone else. We even have had the same dream at the same night. We believe we are soulmates. However, I don't know if his definition of "soulmate" includes romantic relations. We've only talked about our souls knowing each other in several former lives. What do I do? I don't think telling him will ruin our friendship. We've been through too much together for that to come between us. So, I'm not afraid of that. I'm afraid of rejection. How can I bring this up to him?

Today I spoke with "Joe"'s sister. Of course, being the big mouth that she is, she told me that she talked to him about the above situation. He said, "S and I go out and we have a good time. If it's going to happen, it will happen naturally. Not because our families are forcing it on us." Let me clarify that his sister brought the issue up without me starting the conversation. I said, simply, that I wouldn't mind being with him. I didn't want to get too excited because I know how big her mouth is. So, again, how can I start a conversation? I'm not good at initiating but I need to before he starts dating someone else again.

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  1. Just tell him.  There is no perfect time.  If you plan it out too much it might end up making it a little awkward.  Go out for drinks with him, a little alcohol probably wouldn't hurt.  Don't misread that for that for getting trashed, you want him to take you seriously!  Good luck, from what you've explained I'm pretty sure he feels the same way!


  2. I say just go in for the kill. When you two are alone hanging out, let's say on the couch or saying goodbye or something, just kiss him. But not for like 2 seconds but until he pulls away. That way he nows your interested, it's the "natural" way he wanted and it'll help him imagine you two together/realize it's meant to be.

    Good luck with whatever you choose though!

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