text: what to wear on a date? i'm a single mom over thirty,but i still dress a bit trendy.haven't been on a date in a while,so i'm wondering what's appropiate for dinner and a movie? is there such a thing as being overdressed? and i'm not really a "jeans" fan.... it is not out of the question to ask him what type of place you will be going for dinner so that you can dress appropriately and more along the lines of what he will be wearing.  (don't ask him what are you wearing?)  if it is nice casual:  you don't have to wear jeans, but down play the blouse if you are going to wear dress pants... be comfortable, yourself, and not too sexy. a little sexiness is usually more sexy than showing lots of skin.  you can be classy sexy as opposed to the trashy version.  if you can stand the jeans... i would say try it... add a nice blazer or blouse and some skinny heel sandals or pumps (trendy) and just make sure the face is flawless and the hair is hot and the jewelry is nice, nails nice... the shirt and the pants  - won't matter.  if you wear slacks... wear a jean jacket with a cute tank under it... makes it more casual, but still cute.  wow him with your interest in his conversation and how easy you are to talk to and have ongoing laughter and conversation.   if you go out again... and you can get more dressed up for that wow him with something sexier and that way he is getting to see a different side to you.  make sure if you like this person that you can hold a conversation and that you come across intelligent about something.... he will be impressed, no matter if you are a waitress or a lawyer... if you are smart - it shows.  some men find it a turn on.