This may seem like a silly question, but I absolutely love dresses and wear them no matter the occasion. We're going to dinner and a movie, but I'm afraid that he will think I'm overdressed or something.
Just make sure it's not too too dressy of a dress. Wear a cute casual one with maybe some nice flat shoes. Heels always make a dress seem more formal (in my opinion). If you feel comfortable in dresses go for it, I don't think he'll mind.
id say its definitely okay...so your going on a second date, that means the first was good enough for a second to happen...him seeing you dressed up will make him think "oh she looks nice just to go out with me" it will give him confidence as well as yourself.
Dresses are hot, and most guys are going to prefer it over jeans or something. skirt might be too far depending on the guy, but most of the time is OK as long as its not too short will give the wrong impression.
Of course! Sweetie, if wearing a dress helps you feel more confident, than go with it.Besides, I'm with you.I live in dresses, skirts and heels. Select something pretty and tasteful,and you'll be fine.You don't have to go overboard,with the glitz and glam,just something cute and maybe pair it with a modest heel pump,something aong the line of a T-strap or Mary Jane.You'll be a knock-out.Good Luck!