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.
Most Helpful Girl
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.1