Dear Millie,

There’s this guy that I’m into but I am not sure how to ask him out. I’m worried that he’ll reject me.

We’ve been friends for a while now and we know each other pretty well. Sometimes I think he’s interested in me too, but I might be imagining it. He’s not a very outgoing person, so if he was interested in me, I don’t think he would have the guts to tell me.

I can’t stop thinking about this problem. What should I do? Am I overthinking things?

Sincerely,

Crushing Caitlin

Dear Crushing Caitlin,

If you are thinking this much about your friend, you should definitely ask him out. If you don’t, you’re going to be constantly thinking about what could have been. 

From what you say, it sounds like if you ever want answers, you are going to have to make the first move. If he does like you then he’ll probably be relieved that you asked him.

If he rejects you, but is a true friend, you guys should still be able to hang out.

If things go really bad there’s always someone else around the corner.

I wish you luck.

Yours Truly,

Millie