Dress for second date?

I have a tendency to feel lots of details are needed in these so bear with me.

I'm 26 and just about 3 months ago my first serious relationship ended. I've had casual relationships and flings but I've gone at things very backwards and I'm often shy and nerdy so it's hard for me to ask women out etc.

I met this woman online and invited her to coffee on Friday. We hit it off, and we're going to dinner on Wednesday. Nice place. Not too fancy, but not cheap. Anyway, my last girlfriend made the critique to me that I dress like an old man. I like to wear sport coats and nice slacks, or good jeans, and a collared shirt. I've been skipping the jackets and wearing sweaters more lately because everybody around me dresses far too casually. lol

So, on my date on Friday, I wore my best pair of GAP jeans (uncomfortable, but they look good), and a nice shirt with a leather jacket.

Wednesday, I was thinking of dressing up slightly more. She has a professional job and was dressed as such on the date because she came from work. She very well could be doing the same on Wednesday.

So, a simple shirt with black dress pants, and black dress shoes? I have a nice charcoal sports jacket, but I don't know if that would seem 'too formal' or 'too old'. That said, my ex is a few years younger than me, and still likes to go out partying and dancing more than I do lol. The woman I just met is my age and is admittedly more reserved and quiet, so she might actually that in me. IDK.


Most Helpful Girl

  • I'm so feeling you. I was thinking a white dress shiryvabd black slacks with black dress shoes. Put the blazer or sports hot in the back seat so after you pick her up you will know if you need yo put it on or not. Good luck. Wish there were more guys who thought like you.


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