Dear Don Cusack – The Overweight Lover

Taken from formspring:

How do I tell a lady that she needs to lose weight?

This is a very hard question to answer.
You do know that telling a woman she is fat is on the level of slapping your mom right? I mean its no real way to say it and if its out of your character [...]

Dear Don Cusack – The BFF Dilemna

Taken from formspring:

Is it ever appropriate to tell someone that you might be talking to that you fucked their best friend. especially, if it was in the past, once & it did not mean anything. or to the grave?

- Anonymous

This is a tricky one and by the way its worded its making it seem as [...]

Dear Don Cusack – Young Shy Guy

Welcome to the inaugural advice column! Let’s just hope I don’t ruin your lives too bad…
‘Young Shy Guy‘ writes:
I’m not sure if this even counts…
I’m still in high school and there is this specific female that has caught my eye. The main issue is, I don’t know her at all. So any advice on [...]