Dear Ali,
So I can’t be sure, but I just saw my boyfriend Jeff holding an empty tin cup as he searched through garbage, and I think that’s when he got the shirt he wore to dinner last night, which smelled like fish. Is it just my imagination, or am I dating a homeless man?
-Homeless Or Being Onest

Dear HOBO,
He sounds pretty homeless. But is he just homeless in the way that all New York teenagers are homeless after a weekend out (reeking of vodka and vomit, experiencing a harsh re-entrance of sobriety, and not knowing where their Fendi baguette is), or is he actually does-not-have-a-house homeless, begs for money, uses public transportation homeless. Maybe you thought he was cute because he was in a band, but the band was really just him and his two-stringed guitar and blind dog? It’s an easy mistake if you’re on enough oxycontin. This is tough. I’d have to say the first thing to do is figure out if you contracted AIDS from him. If so, he’s probably homeless.

Dear Ali,
I totally saw you the other day and you just walked right past me. What the fuck, whore?
-Say Hi To Me

Dear Rachel Shirazi,
Friends don’t fuck other friends’ dads. Just because you’re Sephardic doesn’t make you special. It just makes you hairier.

Dear Ali,
So my teacher says my body is supposed to be going through lots of changes right now but im 17 and people still say i look like that kid from Home Alone 2. I just want girls to stop petting my head and saying “fourth graders go to school over there.” Please help.

Dear Childish,
Awwwwww!! How cute are you?? Do you have like one of those weird genetic diseases that fucks up your age??? That’s adorable!!!!

Ali Weinberg has been giving advice to teenage girls for a while now.

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