Sasha Answers: Should I move on my best friend’s brother?
Sasha, basically I'm in love with my best friend's brother, D. The feelings started creeping up about 3 years ago when H (his sister and my best friend) got married. We were both in the wedding party and were spending more time together then we usually do. Although I am extremely close to their family and spend a lot of time with them. Anyhow I thought after the wedding something might happen as we were pretty much hanging off each other (other peoples words), but nothing did. Neither of us have been in any serious relationships in these past years and now being in our late twenties I'm finding it hard to just ignore this anymore. My thoughts are that he feels the same for me, but I really have no idea and am finding it hard to go about finding out. Our situation is difficult with the whole me being so close to his family, but I also feel extremely comfortable around him too. I've been trying to start up more conversations with him via text and messaging and have also tried to get some one on one time with him (we never hang out just together) but with no success on the alone time. And then this weekend I finally got up the nerve to tell H that I have feelings for her brother, her reaction was good, neutral which is what I was hoping for, but now comes the really hard part of bringing it up to D and I'm extremely stumped here. I don't know how to go about it without messing things up, especially if he doesn't have the same feelings for me. I keep getting different opinions from friends, but basically what it comes down to is I'm chicken sh** when it comes to this! Help!
B, if I were you I’d play this one out for a bit longer before you barf up any real feelings to him. I don’t want to be a buzz kill, but the signs haven’t been super awesome in your favor -- just yet. The fact that you’ve been trying to hang out with him solo and he hasn’t bit once is a slight red flag.
If I were you I’d wait a week or so and then send him one more direct hang-out text. If there’s radio silence or some wishy washy bullsh-t, then I think you may have your answer.
Now I know it’s probably not great for your best friend to be put in the middle of this, but who the f-ck are we kidding, she’s your best bud so I’d ask her to do some recon and be frank about whether she thinks he’s in or out. That way you can get the answer and still save some face.
Fingers crossed that it works out! Keep me posted!