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Last week, my wife Cupcake and I were going through some old photos, in an actual photo album with the sticky clear film that gets all brown on the edges… oh wait, you youngsters may have no idea what I’m talking about. You see, back in the olden days, photographs were taken on cameras that used FILM. This film would then have to be taken to a photomat to be processed by some nerdy kid in a darkroom who got to get a glimpse into the lives of everyone in town who frequented his little shack in the middle of the mall parking lot.

But I digress…

As we were looking through old photos (now that I think of it, that nerdy kid at the photomat probably got a good laugh at these), we came across some pics of us when we were first dating. That’s when Cupcake reminded me of the outfit I wore on our first date…

She described the outfit as my “waiter” outfit. Plain black pants and a white, button-down shirt. I thought I was dapper as heck, but hey, looking back I guess I definitely needed help in the wardrobe department!

Well, this got us talking about what men should NOT wear on a first date. Fellas, don’t wear sweatpants, don’t wear sneakers and for the love of all that is good… DON’T wear you Waiter’s uniform!

We hit the streets of New York and asked the ladies and men of SoHo what they thought men should NOT wear on their first date with a new flame.

Here’s what they had to say…


Have you taken a trip down memory lane recently and found yourself shocked at the clothing you used to think was fashionable? Have you ever worn your best (but ended up being the WORST) outfit on a date? Let us know your horror stories in the comments section below!


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