Reminds me of George Costanza and the Timberlands
As for the upcoming online date, I say wear it. Online dating is normally just a smash and grab so best to fake it. Chances are it wont amount to anything meaningful. Also a good chance she cancels last minute.
Not everyone's looking for the smash and grab though, especially as you get older.
If OP really wants to get the answer to this question he should ask some females which would shed a lot more light on this then a bunch of middle aged men
I agree but the majority of people on dating apps are (women for sugar daddies, men for sex). This isn't the same idating game it was back in 2002. I think it's better he plays the field for a bit, takes on some ground balls and a little batting practice before heading to the majors. A good toupee will help his confidence and game. It could also lead to some hilarious stories.
And more importantly, it's generally a bad idea to ask women their advice on dating. They'll tell you to be a nice guy who leads with honesty and other nonsense. As they say, you want to ask a fisherman how to fish. Don't ask a fish.