"He says I'm out of his league"

Dear Megan,

I have no doubt in my mind he likes you – after all, he tells you all the time! – but answer me this: do you really want to be with someone who clearly doesn’t have a backbone?

Just look at the facts. If this guy doesn’t want to be with his girlfriend anymore, than why is he?

Something tells me it’s because he’s petrified of the alternative. Maybe he doesn’t want to be with her anymore and he’s dying to date you instead, but his relationship (no matter how bad it is) is comfortable and familiar to him. And leaving that, even if it is to possibly date you, is the scary unknown! While it’s human nature to cling to the familiar, when we let fear paralyze us into staying in a situation that really doesn’t benefit us anymore, we ultimately lose.

So what’s your fraidy-cat crush doing? He’s trying test the waters to ensure that if he really does break up with his girl, you’ll be there to pick up the pieces. He doesn’t want to let go of a sure-thing for something that may or may not happen. Thus the reason for his self deprecating behavior; by telling you you’re out of his league, he’s hoping you will respond by saying how ridiculous of a notion that is, and that he’s perfect for you and he’s the one you want!

Forgivable behavior? Yeah, we’ve probably all done it at least once in our lives. But appealing? Not so much. Like I said, I don’t doubt he’s crushing on you, but what concerns me is that if he’s unhappy in his relationship, he should be able to end things with our without the promise that you’ll be there for him. And while we all struggle with self-esteem, it seems to me that if you were his girl, you’d spend more time stroking his ego than anything else!

Good luck!

Marissa