Ask Drew: He Showed Up Wearing a Hoodie!

Q: Dear Drew,

I went on a first date with a guy who seemed really promising. He has a good job, seems motivated, and was nice and funny when I met him. But I show up to the date (at a very fancy restaurant that he chose) and he was wearing a grey hoodie. Am I being too judgmental to write him off for his bad fashion sense? If he actually wanted to impress me, don't you think he would have worn something a little nicer?


A Little Effort Would Be Nice

A: For starters, I'm biased because as I'm writing this I'm wearing a grey hoodie with salsa stains on the front. Then again, I'm not trying to impress you.

I'd like to say you're being too judgmental, but I know how important fashion and all that stuff is for women. My own wardrobe consists of Hanes t-shirts and bargain brand jeans, so I'm probably not the person to ask. But my judgment lies here: although I dress like I have foodstamps in my wallet, I do recognize dumb decision making. And wearing a hoodie to a fancy restaurant on a first date should at least register as "stupid" with this guy. I wouldn't do it, but then again I wouldn't be at a nice restaurant. We'd be at a sports bar so she at least understood the product of guy she was getting.

Final thought: he's sending mixed signals. Get your act together, dude. Either be a baller or a bum. It's your call. Keep an eye on his behavior on your SECOND date. (Read: he gets a rose! One more chance!)


Drew is a single guy living in Los Angeles. When he's not bar-hopping with a friend's golden retriever to convince women he has a soft side, he's taking them on short-lived dates. His fickle dating habits and "perspective" almost guarantee he'll die alone. All opinions are his own. Got a question for Drew? Ask away...

Tagged in: advice, dating, relationships, ask drew,

Lifestyle / Relationships



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