I like my friend’s brother.

Okay…it started a few years ago when I first met my friend’s younger brother. I didn’t think about him at all in that relationship kind of way because we were both seeing other people at the time. Some time went by, a few relationships here and a few breakups there and poof, we met up a few weeks ago.  It was really nice seeing him. He’s now divorced and moving on…I’m single and enjoying life…the difficult thing was, I realized I kind of liked him.  

So, I guess, my dilemma is…I’ve kept in touch with him more than his sister and was wondering if it would be awkward for family dynamics. Secondly, do I  tell him…”Hey, I kind of like you” and take it from there, OR, do I just acknowledge that I have these feelings and move on? I don’t want it to be awkward for anyone, but probably also afraid of a little bit of rejection.  

What are my options in this situation?

Many of my friends have hot brothers. Sometimes, this has totally worked to my advantage (you know who you are, hot stuff) and sometimes it’s resulted in awkward and embarrassing situations that made me want to get reconstructive surgery on my face and move to Australia (you know who you are, but we will never acknowledge knowing each other ever again so it doesn’t matter).

You’re coming from a hooray! standpoint. You’re better friends with the boy than the girl, he seems interested in spending time with you, and as long as the two of you don’t openly discuss the intricate details of your weekend getaway in the Poconos at the family dinner table, it’s okay for you to date the brother. It’s absolutely fine, and even sweet of you to be concerned.

And I wouldn’t tell him that you like him. I hate when people do that; it adds needless pressure. I’ve been in situations before where I totally was into a boy, and as soon as he how much he liked me, I thought, “Eeeeeeeeuw,” and never wanted to see him again. So instead of making a grand proclamation, maybe just try to spend some time with him. Have fun together. See what happens. It’s okay to invite him somewhere–“Hey, Bob, want to go to the races this weekend?”–as long as you don’t awkwardly invite him somewhere. (“Hey, Bob, I really want to get into your pants, want to go to the races this weekend and then make out in your car?”

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