Back in the day, when Gigi still lived in Philly, I fixed her up with a friend of mine. This friend, we will call him Dane, was smart and funny and paid particular attention to his appearance and I thought he was good looking (as did other friends of mine) and so he and Gigi seemed like a great fit.
Dane invited Gigi to a Bruce Springsteen concert for their first date.
And of course, Gigi called me immediately after (I told you guys, this is what happens. You are not just taking her out, you are taking out all of her friends as well). Her first comment to me was, “You really think he is cute?”
Umm, yeah, I thought that was pretty much a given.
Wow, now I'm curious.
“Well, I don’t know, he had a black-eye so that didn’t help.”
“He said he didn’t typically get into bar fights, but then he wouldn’t continue.”
Huh. But I mean besides the swollen black eye, you didn’t think he was cute. You weren’t impressed by his awesome hair?
“Uh, he was wearing a hat.”
What the Eff?
Here I have been trying to help you fellas out with dating advice, having no idea just how much help you needed. So now we are going back to the very basics. Personal appearance.
Now, if you were in a bar fight the night before a date, and it is a date you can’t get out of (like a Bruce Springsteen Concert), well then there is very little you can do (as I would never recommend lying). Of course, if you are at a bar the night before a first date you might want to do everything in your power to avoid getting into a fight. Just saying.
Now, let’s assume you didn’t get into a fight and let’s talk outfit starting with the hat.
Understand if you show up to a first date wearing a hat, we girls are going to think one of two things (neither of them good). You either a) are losing your hair, or b) didn’t shower today.
If you did shower and have a full, luscious head of hair (like Dane’s) then I don’t care if you are going to a concert (where under other circumstances a hat would be appropriate), keep your lids at home.
If you don’t have hair (or are losing it), I would still advise leaving the cover-up at home. Covering it up indicates to us you are embarrassed by it and thus not confident and since you aren’t fooling us by hiding it, why not try fooling us by pretending you don’t care.
On the other hand, if you are wearing the hat because you didn’t shower, well that is just gross and disrespectful and you deserve never to hear from us again.
Another huge no-no is white socks. Seriously guys, I understand you look better in white socks when you get to the stripping down portion of the relationship. But until then, keep the socks dark.
As for the rest of the outfit, well that is tricky. Depending on where you are going and the day of week it could vary. T-shirts are perfectly okay for a date to a rock concert or a ballgame or a weekend date doing something outdoors. However, if you are meeting for drinks downtown, even if it is a relaxed atmosphere, I think a shirt with buttons is a better option. Even if it is just a golf shirt. Good jeans are always okay in my opinion, but by good jeans, I don’t mean faded or dirty or carpenter jeans (yes, for all the gays that read this blog they still make carpenter jeans and worse, men still wear them).
I would recommend against anything displaying a “sense of humor” your date might not get. Like a t-shirt that reads “6.9 Even better without the period” or really, really short turquoise shorts. I am not saying you need to get rid of these items (well, maybe you should get rid of that t-shirt as it is just -- I don't even have words), I am just saying you may want to wait until a later date to break them out. You know, when she knows you better and gets that you don’t really think you look good in those shorts, they are just your way of telling the world that you don’t care what you look like.
Even though you obviously secretly do.