Dear Yenta,

I have a friend who always goes for the “bad boy” that isn’t
interested. She becomes close friends with these guys and then tries
to draw inferences from the close friend relationships like “we do a lot
of date type stuff together.” I don’t want to hurt her feelings by
telling her they just aren’t that into her, but I feel kind of
dishonest just smiling and nodding every time she talks about these
“relationships.” I obviously think she is great and that the right
guy is out there for her, but listening to her stories tells me he is
not these wild dudes. I also think she is depressed, so I don’t
want to rock the boat and send her spiraling any deeper. What would
you do? Am I being a good friend or should I tell her what I really
think?

-Smile and Nod

Dear Smile and Nod,

What is being a good friend? Is it blindly supporting someone through hard times? Or is it helping someone see themselves more clearly when they have gone temporarily blind? Or, really, is it a balance of both?

Too much truth burns, we all learn that the hard way. But too little makes you a wet rag. All your fear of being honest with your friend sounds like you are enabling her depression. That, and you sound a little afraid of her.

There are ways of saying, “he isn’t worthy of you,” “you deserve someone who…. Listens, cares, shows up, etc.” You don’t need to bash her choices, but you can insinuate that there are more options, that it is ok to dream big and expect bigger results. One element of depression is a narrow and skewed vision of the world. Without commenting on her sour lovers, you can still easily coax your friend into believing she deserves more.

Also, teetering on the edge of a depressive downfall, your friend is responsible for how deep she lets herself sink. It is nice to be there, but try not to be too Brandon Walsh or Dan Humphrey. This means let her worry about her, and you about you, while still showing your love and positivity so she might find her own way out of this quagmire.