There are three extremely trying times to choose the right clothes for the occasion: job interviews, first dates and meeting the parents nights. First date dressing is tough because you usually don't know the other person well enough to predict what will be attractive to him. You want to look fabulous but not unattainable, chic but not cheap. Add to the problem that you may or may not be familiar with where you are going, and you have the perfect explanation for women who choose to stay home in a chenille robe with a bottle of Two-Buck Chuck and a box of microwave kettle corn.
Let's go over some first date dress basics. Maybe you'll get lucky and I'll have an idea you haven't already considered.
Any ideas on where you going on your first date?
If you can, have a conversation with your date to find out where you're going. But be simple with your questions to make sure you dont' sound to controlling. This will help immeasurably, even if you can just get a sense of the formality of the occasion. A good tip is it's always better to be a little overdressed. We've all at some time or another ended up at the baseball game in a frilly, walk-in-the-park sundress, which beats hell out of going to see Itzhak Perlman wearing skateboarding pants (which happened to me once).
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Good Date Movies For At Home Dates
If you are still on your first few dates with a guy or girl, stay away from the serious dramas, bloody action flicks, and overly sad romantic (mushy-gushy) movies. Try sticking with up-beat, light hearted movies that are in the romantic comedy genre. He'll enjoy the comedy and you can enjoy the little bit of romance.
See a selection of recommended romantic comedies that are great for first dates or newly dating occassions.
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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).
The Coffee or Lunch Day time Date
If your date has read the advice columns that say to take the pressure off by having a coffee date or a daytime date, you can expect to dress more casually. In this case, it doesn't much matter what you wear (as long as it's neat and put-together), because you already know they guy is either nervous or non-committal. In the first case, you can graciously put him at ease: in the second, you can keep him guessing.
Choice of the low-impact date does not indicate a man's potential as a long-term romance. Cheapskates and guys who aren't sure they want to "really" date will choose the daytime scenario because it's simple and cheap. They get exposure without investment. Nice guys and shy guys will choose this date because of its low-drama possibilities. They get to be with you without having to act like Cary Grant. Nice guys and shy guys will either up the ante or wait quietly in agony for you to express interest in seeing them again. Cheapskates will expect you to pay for your own coffee. Non-committal guys will say they'll call you, then won't.
I want to add an aside about the coffee comment above. I struggled with this question for years, and paid for a lot of coffee (and dated several cheapskates) until I figured out the flaw in the feminist tao. You see, feminists are expected to buy their own stuff, and sometimes the guy's stuff too, in order to show how liberated we really are. The mindset is, if you're going to be "freer" than non-feminists, you should expect to pay your own way. The fact is, if you adhere to this policy, you will be less free than other women because you will have less money. The other important fact to consider is that women still earn about 60% of what their male counterparts earn. Until we're paid equally, men should always buy the coffee.
There is a creepy idea (often unspoken, often assumed) that if a woman in not planning to become sexually involved with a man, she should pay half. If you ask me, that's selling sex pretty cheap. I say, forget all that crap and hang out with guys who don't have a problem buying your coffee and dinner or waiting until you're good and ready before making any moves on you. Besides all that, if you're dating because you're looking for a commitment, you want a guy who's going to be willing and able to pay on a mortgage, and later, for child support. His willingness to shell out $2.50 for a latte is a very slight indicator of his potential, but it's better than nothing.
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'".
If you get asked to a wedding on a first date, you're either with a social inept, a potential stalker, someone who's been in love with you from afar for ten years, someone who thinks it'll be a good way to get laid, or someone who has nothing left to lose. For these reasons, I would not accept such a first date, eliminating the need for discussing what to wear at such a debacle.
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.
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