Preparing for Date #1: Guidelines for Women

Recap: Everything is planned and he's going to pick you up later this (early) evening. What on earth do you wear?

If the restaurant is high-end (such as Scupper Jack's):
A. No jeans. Wear nice-looking pants. Be sure to iron them
B. Wear a short sleeve (summer) or long-sleeve (winter) shirt. Once again, iron it
C. No tank-tops and please, don't flaunt anything. Make sure any straps or undergarments cannot be seen
D. No perfume (at least, not on date #1)
E. Wear decent shoes. No high heels

If the restaurant is semi-casual (99, Chilies, Outback, Applebees, or somewhere similar)
A. Jeans are okay, but not if they're ripped
B. Wear a nice shirt, weather-permitting. No tank-tops, and hide the cleavage. It will distract him
C. Don't forget to iron them.
D. No perfume
E. Wear regular shoes. No sandals or slippers (I've seen people wear the last two, and it breaks my heart)

If the restaurant is in the North End
A. Save this for a special occasion, and wait until you have been dating at least three months
B. Dress pants are a must (or a casual dress)
C. Wear a nicer shirt than normal but keep the cleavage hidden.

Other guidelines:
1. Brush you teeth
2. Shower (this includes washing your hair and shaving)
3. Don't go too heavy on the makeup and stuff. My personal opinion: If people notice, you overdid it.
4. Hide the tattoos
5. Leave the cigarettes and matches/lighter at home.

Up next:
Picking her up: Guidelines for the ride