What should I wear?

I'd say wear something that reflects your personality. I hate it when girls dress one way for a first date and every other time you meet up with them they look and dress totally different. Dress like yourself and wear whatever you feel comfortable with.

I would dress a little nicer than normal, but not TOO nice. I would probably wear just a polo shirt and maybe some jeans/khakis.

Firstly, make an honest impression and a statement about your style and attitude. Wearing something that'll reflect your personality is a bonus and shouldn't be an exception. Aim for middle ground for date one. Neutral colors, classic styles and great accessories are always comfortable, especially if you don't know where you'll be going for your date. Decide what makes you feel pretty, sexy, confident or comfortable. If you think you'll feel better in jeans rather then a skirt then wear jeans! Its really that simple. Choose your colors. That little black dress, silver jewelry and an exotic shawl could be stylish and sophisticated. Pastels, gingham or soft lines suggest softness. Be yourself. If you're at ease with lower necklines and revealing clothes, go for it if it feels appropriate. Think comfort. Stiletto heels, new styles or a skimpy skirt may make you uncomfortable and distract you from your date. Try ballet flats or any other low-heel shoes that you'll feel comfy in! Flats, tho, are great under jeans AND a dress, so they are a good choice. A nice pair of jeans with a tank top and a buttoned sweater will look good. Or A nice simple dress with flats can work out as well! Try wearing a simple t-shirt and a sexy skirt to spice yourself up.

In whole, as long as you are comfortable. Your look should work out smoothly!