Tips, Advice and Ideas on What to Wear and How to Act on a First Date

Advice On Shoes: Comfortable vs. Sexy
Find out if you will be walking, and if so, how far. If the guy's at all exercise or nature oriented, double or triple the estimate he gives you and you'll probably come close to the truth. (And if he flat-out lies about how far the walk is, don't go out with him a second time. Use this estimate to choose the durability and support of your shoes, and if you aren't confident, pack along some cuter, (invariably less comfortable) shoes in a bag.



The Little Black Dating Dress
If you're having the classic dinner date in a place created to impress women on first dates, the choice is simple. There is no substitute for the little black dress (known in fashion circles as LBD). It is equivalent to the men's fashion outfit: the classic dark grey suit. If you don't have one of these must-haves, get out the catalogs, visit your favorite designer on-line and choose the version that suits you best. Add a purse, pumps and stole to match, and there you have it. For premium wearability, your LBD should be of medium length, and although the classic is sleeveless (meant to be worn with opera-length gloves), choose the sleeve length based on your comfort.

The little black dress saw Audrey Hepburn's character through most of "Breakfast at Tiffany's", and there's no reason why you shouldn't wear yours to parties, first dates and anytime you want to feel absolutely classic. Vary your jewelry and accessories, and you can wear it to work, for lunch in the park, shopping with the girls and dancing with the boys (or the other way 'round, if you prefer).

Who Should Pay on the First Date? Guy vs. Girl
Although you shouldn't expect to pay for things on a first date, bring along plenty of available funding. At least enough for cab fare home.

If you think he's the sincere type and you want to show that you like him (without saying anything scary like, "I like you"), you might add an element to your daytime-date outfit that you don't wear every day just to acknowledge that something nice is happening on this day. Wear a pair of pants one shade nicer than what you usually wear, or trade walking shoes for pumps. Don't make big changes in makeup, though. Men have definite feelings about and reactions to make-up, and if your face looks noticeably different, he will become frightened and disoriented.

Wedding and Special Occassion Party Dates
Part of the way we judge a potential relationship is by the events we attend together. In straight relationships, going to a wedding with a date is an automatic increase in that relationship's potential intimacy, if the man has invited the woman along If the woman invites the man and he's not ready for the commitment of witnessing someone else's commitment, he will either decline, bail at the last minute, or attend with great discomfort and break off the relationship soon after. In same or opposite-sex couples, asking someone to attend a wedding with you is a bold maneuver to be taken on only if you're sure your relationship is ready for it, or if you want the other person to break up with you. (A sit-com scenario. Someone asks a woman, "What do you say if you want to get rid of a guy?" Her answer: "I say, 'I love you and I want to have your babies'".

Dates to Baseball or Sporting Event Games
Jeans or chinos, a hat, layers, and bring a thick sweater if you live near the sea. Nothing too sexy, nothing that can't be washed if you have beer spilled on you or if you sit in gum.

The Sleaze Factor: Don't Dress Too Sexy
It's tempting to dress as sexy as the magazine models, but in the harsh light of day or the romantic candlelight of evening, it rarely works out that way. Sexy has a way of turning sleazy when you least expect it. The artistry of dressing to impress means utilizing restraint, so save the micro-minis and see-through tops for those rumpus-filled evenings at home and opt for looking pretty in public.