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You Asked: Should I Speak Up?

Dear Sugar--

I have been sleeping with one of my best friends for almost a year now. It's not every day or every week, but anytime we are together especially when there's drinking involved. It's not like we are "buddies" because we don't call each other, and one time he even said, "it just happens." I think that if something "just happens" there is something there. It isn't casual like a booty call if you will. About a month ago, I went to his house and there were candles lit, we slow danced and ended up having sex. Two weeks later a similar situation happened where we were with all my friends and were telling each other how much we loved each other.

I am a person that talks myself out of relationships because I was hurt very badly before. My friends all tell me that he loves me but I guess I am just scared. Our families have been friends since I was 14, and my brother and him grew up as best friends so as you can see, there are many obstacles here. I don't know what to do, I do have feelings for him, but how am I sure that they are true? Do I say something to him? HELP ME PLEASE!!! -- Unsure Sally

To see DEARSUGAR's answer

Dear Unsure Sally --

Yes, I would agree, it does sound like there is something there, but if both of you are too timid to speak up about your feelings, your window of opportunity to take your relationship to the next level might slowly pass you by. You say there are many obstacles in your way, but I see them as positives, not negatives. But with that said, make sure your feelings for him are real -- make sure it's not just the chase and the game of it all that is attracting you to him or else your close connection could get a little sticky.

Being afraid of getting hurt by putting yourself out there is a totally valid fear, but if you don't give it a try you might never know the outcome. It isn't like there is nothing backing up your assumptions here. Since you say something happens whenever alcohol is involved, why don't you try hanging out with him when alcohol isn't involved. See how you like being around him sober. If you still have a great time together and if you're still attracted to him, than you know your feelings are legit.

Although wearing your feelings on your sleeve is no doubt daunting, sharing them with this man could be well worth it in the long run, so my advice to you Sally is to go for it! From what you're telling me, it sounds like you are both on the same page just too afraid to take the plunge. Good luck!


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