First Date Dos and Don'ts

Be honest, be real — but, whatever happens, don’t be afraid. Our dating expert is here to help.

By Sherry Amatenstein, LMSW

Q. I’m 45, an entrepreneur, and divorced 18 months. I’m about to go on my first date in 15 years and I’m terrified. I have no clue how to do small talk and no idea how much I should talk about my marriage. Do I offer to pay? What if he tries to kiss me? What if he asks me out again? What if he doesn’t ask me out again? Please advise. — Connie

A. Feelings about this event typically fall somewhere between a visit to the dentist and jumping out of a plane — there is fear and dread mixed with the exhilaration of the unknown.

How not to behave? Listen to a man who in the past few months has been on a baker’s dozen of dates with women who fit this profile: "Some have been so scarred by love their trust is gone," Jim McClure categorizes briskly. "I get asked questions right off the bat like: ‘You’re not bipolar, are you?’ and ‘I hope your birthday isn’t July 15. Two of my exes were born then,’" explains the 48-year-old Illinois technology public relations executive. Another category is the frightened naif: "They exhibit defensive body language — crossed arms, wincing — if I ask any personal questions. My heart goes go out to them. But they don’t wind up winning my heart."

What works for him? "It’s great when someone can say, ‘I’m scared. This is the first time I’ve done this in a long while.’ This means she’s honest and unafraid to share information about herself."

But not too much information. It’s not a great idea to wax on and on about the last person you dated back in the Stone Age. Discretion is the better part of first dating etiquette when it comes to disclosing your undying hatred or enduring love for your former hubby.

So what’s left to talk about? Depressurize the evening by pretending you are dining with a potential new friend rather than a potential Prince Charming — or Prince of Darkness. Conversational fodder should then more easily come to mind and to tongue. Choose from this menu and invent your own: current events, movies, the gridlock you encountered on your way to the restaurant, how much you like his tie….

On that theme, draw him out. Erica Manfred, author of He’s History, You’re Not: Surviving Divorce After 40, comments, "If you’re too nervous to think of anything, ask him questions about himself. Men love to talk about themselves." Just don’t inquire too deeply about what went wrong in his marriage. Manfred, 55 when her husband announced he was leaving for a younger woman in 2000, offers another tip, "Older women tend to be too accommodating and eager to please. Pretend to be a gorgeous actress and ask yourself what she would do in this situation."

On the "to pay or not to pay?" front, the consensus is it’s polite to offer but don’t be insistent. Manfred warns, "If he doesn’t readily pick up the check on the first date it’s a sign he’s a cheapskate!"

No matter how old you are, a first date is like high school, particularly when it comes to the denouement. If he leans in for a goodnight kiss and you like him, a little tongue hockey, not to mention agreeing to a second date, is okey dokey. If not, a brisk handshake and, "It was very nice meeting you. I wish you well" should get the point across that this is all she wrote.

If he doesn’t ask you out again, and you weren’t interested anyway, ask yourself why your ego is so in need of stroking. If you would have jumped at the opportunity to see him again but he’s indifferent, take comfort in the fact that you no longer carry the "burden" of being a born-again dating virgin! You’re back in the game. Congrats and commiserations.

Do you have a tough question about dating or relationships?

E-mail Sherry at and your question might be featured in an upcoming column.

About Sherry Amatenstein

Sherry Amatenstein, LMSW, is the author of Love Lessons from Bad Breakups and Q&A Dating Book. She runs dating seminars around the country and does private coaching — not to help singles marry in 60 days, but to uncover their blocks. She has given relationship advice on the Early Show, Regis, Inside Edition, CBS News, VH1, BBC, and many other programs. Her philosophy is that the most important relationship you’ll ever have is with yourself.

Originally published on, November 2008.

First Published Mon, 2009-04-06 18:05

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