Reinventing Romance: Dating Etiquette

Who pays on a date? Over 40 dating expert Sherry Amatenstein answers this and other questions on grown up dating etiquette

By Sherry Amatenstein, MSW

Who Pays and Other Dating Questions

Q. I am divorced after a 17-year marriage. I’m not in a hurry to marry, but it would be nice to spend time with someone. I have several big questions: First, who pays? One man that I dated several times told me that it annoyed him that I never paid the restaurant check. What’s the "norm" these days? Second, is it acceptable for a woman to ask a man out? And third, when do you have sex? At this age do you just "do it"? Or is there a "three date" or "three month" rule? I love who I am. I feel and look good for my age, but this dating thing can be frightening at this life stage. — Bonnie

A. Here’s the bad news: There are no rules. Now for the good news: There are no rules. Explains Joshua Estrin, a Florida Life Coach and author of Shut Up and Listen to Yourself, "This can be a bit unnerving for the traditionalist but also empowering and exciting." Just ask Roz Salz. The 52-year-old Coordinator of Student Activities in New York says, "At this point in my life I trust experience and intuition."

Certainly the "who pays" conundrum does not lend itself to a one-size-fits-all, bubble-wrapped response. A typical norm is that a man pays for the first date. Yet it’s considered proper that whoever asked the other out reaches for the check. Etiquette experts suggest that regardless of who initiated the get-together, if a woman has no romantic interest in her companion she should pony up. Bottom line: there are no absolutes. Bonnie’s date expressed annoyance at her for ignoring the bill. (Did she at least say thank you?) Countless women report trying to pay the tab only to have the man regard them as female black widow spiders who having devoured dinner want to devour them. The best policy, after the first or second date when its clear there’s a rapport and degree of comfort, is to broach the topic a la: "I love that you want to treat me to everything, but it’s important to me to contribute as well."

Can you ask a man out? The worst case scenario: he says no. You’ve been through worse and what doesn’t kill you makes you more confident. Seem too emotionally risky? Invite him on a group outing. Or say a casual, "It would be fun to get together sometime…" According to Susan Winter, the New York author of Older Women/Younger Men — New Options for Love and Romance, this asking without really asking technique, "offers less pressure." You’re still jumping off the board yet ensuring the water below is deep.

When should you jump into bed? The right timetable for sex is the one dictated by your gut. You may feel like a gawky 16-year-old in this scenario, but trust the hard-won self-knowledge you’ve gained over these four and something decades. When it feels right, it is right. If you have doubts, keep your shirt on (and various other garments) until you truly can’t wait to tear off his.

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, MSW, is the author of Love Lessons from Bad Breakups and The 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, VHI, BBC, and many other programs. Her philosophy is that the most important relationship you’ll ever have is with yourself.

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