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6 Keys to a Great First Date

March 13, 2011 | by Rosie Einhorn, L.C.S.W. and Sherry Zimmerman, J.D., M.Sc.

For men: A guide for getting a "yes" to a second date.

In the decades we’ve been involved in dispensing dating advice, we've seen a number of marriage-minded men who – though well-developed in intellect, character, scholarship and other interests – display a degree of under-developed social skills. Often when a woman has a first date with such a man, this leaves her disappointed and uninterested in a second date.

True, if they were to get to know each other, they might develop a connection. Unfortunately, these dates seldom get anywhere because the woman feels she can't admire or respect a man who "just doesn't seem to have his act together."

Here are six concrete suggestions for how to improve the situation.

(1) The Phone Call

The initial phone call to set up the date is where a man makes his first impression. A woman usually prefers that a man keeps the first call to 5 or 10 minutes, and waits until they're actually on the date to find out more about her. Your main goal here is to set up the time and place.

Give her an idea of what you'll be doing on the date. Museum or restaurant? Will you mostly be walking or sitting? If you're thinking of coffee or dessert, let her know so she can eat dinner first. If you'll be taking her to dinner, she'll want to dress appropriately. There's nothing worse than getting dressed up in a beautiful outfit and high heels and finding out your date has planned a hike and a picnic.

(2) Dress for Success

Before a date, a woman will try to look nice for a man – styling her hair, choosing a pretty outfit, and putting on make-up. But she will feel foolish and embarrassed to have made an effort for a man who has holes in his pants, torn shores, a filthy raincoat, or a shirt and vest that looked like they belong on her grandfather.

A woman doesn't need her date to wear designer labels or expensive fabrics. She just wants a man who takes pride in his appearance and knows how to clean, repair and choose his wardrobe. (She'll notice that scotch tape isn't doing a very good job of holding his torn pants hem in place.)

An instant turn-off for women is poor grooming.

Another instant turn-off for women is poor grooming. After a long day at work, a man may need to shower, reapply deodorant, and shave before meeting a date. Most women are not attracted to a few days' worth of stubble, and are definitely put off by that "manly" scent. They are attracted to a man with a good haircut, and whose clothes are clean and in good repair.

Of course, many men will ultimately benefit from their wives' fashion and grooming help after marriage. But they're not getting anywhere near the chuppah if she meets him and immediately thinks, "Oh, no, a Project."

One suggestion is for the man to ask a woman his age how to dress. Most men can find a sister, cousin, or friend's wife who seems to have fashion sense, and ask for her help in selecting a dating wardrobe that's current, well-matched and fits well. Invariably, when a man looks at himself in the mirror, wearing his new clothes, he will feel a lot better about himself. That feeling helps him be more confident on dates, and win the heart of a woman.

(3) Be Prepared

Be on time. Plan for an extra 20-30 minutes of contingency time – for traffic, bathroom break, emergency call from the office, etc. If you're running late, call your date as soon as you realize you won't be on time, not five minutes before you're scheduled to show up. And certainly not a half hour after your meeting time.

Plan where you're going on the date and how you're going to get there. Have a back-up plan in case something unexpected happens, like the restaurant having a fire the night before. If you'd like to let your date choose, rather than ask, "Where do you want to go?", ask her which of two places she'd prefer. She'll be impressed with the forethought you gave to the evening.

Also, make sure you have your wallet, credit cards and cash. It’s not cool to make her wait while you stop at an ATM for enough money to pay for your evening together. And if you're picking her up and plan to take a taxi to your destination, she'll be impressed if you've arranged to have the driver wait outside rather than asking her roommate or her parents to call you a taxi.

(4) Refreshments Served

No matter what your activity, offer your date some sort of refreshment. If you meet after work for drinks or coffee, and you feel like continuing to talk past the 2-hour mark, do it over dinner. You may not feel hungry after a long day at work, but she probably is, and keeping her out later without offering dinner is inconsiderate.

The neighborhood pizzeria may not be the right place for a first date.

Pick an appropriate establishment. You may love your neighborhood pizzeria, but if the place isn't clean and tastefully furnished, it's not a good place for a first or second date. It doesn't matter if she's the 50th girl you've dated – the woman you're with wants to feel that you think of her as someone special, and that you care enough to choose an attractive, comfortable place to spend time together. If you gave the venue of your date a lot of forethought and she compliments the ambiance, don't explain, "Yes, it’s nice. I take all my first dates here."

When the bill comes for your drinks/coffee/meal, reach for it immediately and pay it. If you leave it there, your date will feel uncomfortable as she starts to wonder if you expect her to go Dutch or to pick up the tab. If you wait too long and she offers to pay, immediately say, "No thanks, I've got this." If dinner is beyond your budget, then make it coffee. But pay without hesitation.

(5) The Right Location

Frankly, we think that dinner in a restaurant is not one of the best settings for a blind date. The reasons are practical as well as economical. A blind date should be treated as an opportunity to learn about the other person, to decide if there is enough between you to get to a second date. Trying not to talk with your mouth full, and praying that you don't spill something or get lettuce stuck between your teeth, is not the most conducive atmosphere for conversation. It is also unfair to expect a man to spend a large amount of money on dinner when a blind date may not lead to a second date.

Consider instead going to a place with some visual or auditory atmosphere, like a botanical garden, hotel lounge, art gallery, promenade or other pleasant place to walk, or even an informal, open-air concert. This presents an opportunity to talk, and something to look at and even refer to during those awkward silences. These activities fill about three hours, which is a good time frame for a first date.

(6) Conversation

The goal of this first date is not to overwhelm her with your business prowess, your analysis of the NBA playoffs, or regale her with your escapades in extreme adventuring. A good guideline for conversation is exchanging basic information about yourself and your date – your background, favorite music, where you lived in the past, places you've traveled, hobbies, favorite friends and relatives, studies or career, friends you have in common. This gives you a basis for more in-depth discussion. Anticipate these topics and think ahead of how you will answer.

You can practice having better conversational skills.

When two daters are just getting to know each other, their conversation doesn’t always flow smoothly. However, if you often feel awkward or uncomfortable when talking to your date, there are ways to help yourself develop better conversational skills. Many people have found that working with a coach helped them become more confident about themselves and more comfortable with dating. Others have asked a trusted friend or relative to help them practice being on a date, from start to finish. After two or three run-throughs, they found they were less anxious and better able to carry on a conversation with a dating partner.

Even if you don’t talk much, be a good listener. You can generate topics of conversation by focusing on something your date mentions and asking questions that will encourage her to describe her feelings. She'd like to get her masters in journalism? "Why did you decide to apply to journalism school? How does it feel to see something you've written in print?" Try adding your own insight. "I always thought journalists should be objective. Lately, though, it seems that much of what I read in the newspaper is one-sided. Why do you think this is so?"


If you’re a man who doesn't have his act together, or seems awkward and unsure of himself, these suggestions won't turn you into Don Juan. But they will help you appear more organized, confident and considerate of the woman you’re with. And that should be enough to achieve your primary goal: to interest her into saying “Yes!” to a second date.

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