My best friend and I both like the same boy and I am not sure what to do. And even worse… I think he likes my sister. Send help.

Hello worried soul,

Oh boy! This one’s a doozy.

This may sound harsh, but the way I see it, you and your friend’s feelings are irrelevant. If he’s not interested, unfortunately there’s nothing you can do to change that. It has to come from within him. You shouldn’t have to convince him to date you, he should want to already. And if it is not meant to be between you that’s ok! There are plenty of other, kind, smart, attractive, and willing, fish in the sea.

Now let’s address your sister. Assuming you are correct in your assumptions about this boy’s feelings, there are two possible scenarios. If she’s not interested, then no problem, this boy should get the message. But now let’s suppose your sister’s into it. The feelings are mutual and both are ready to start a relationship.

Now has come the point where you must ask yourself a few key questions. Am I ok with my sister dating this man? If not, ask yourself: Would I feel the same way if it was a different boy that I wasn’t interested in? If not, and for some reason, due to some unforeseen circumstances, this relationship could be truly problematic, then feel free to gently voice your concern. But if you feel they “just don’t seem like a great match” or they “don’t seem right for one another” I would challenge you to let it be. These feelings might be ones of jealousy or anger. Hopefully through acknowledgement, you will be able to overcome them.

Good luck, I know this is a lot to take in,

Earl Grey