The Online Dating Game

If you’re looking for midlife romance, which is more essential, authenticity or a zippy online profile? Two dating experts share their secrets.

By Katherine Lanpher

Dating’s Different Now

Leslie Oren, 43 and single, wrote Fine, I’ll Go Online! The Hollywood Publicist’s Guide to Successful Internet Dating.

Allison Armstrong, 47 and married, founded PAX Programs, workshops to help women and men understand one another.

MORE: How is dating different now?

OREN: Our criteria have changed. In my 20s, my criteria was good kissing. As you get older, you look at lifestyle and intelligence. And does he have children or want them? So, you have to remember to have fun.

ARMSTRONG: Yes. After 40, women get intense. We have to nurture the playful energy that came more naturally when we were younger.

MORE: What’s behind that intensity?

ARMSTRONG: Because of hormonal changes, women become more serious. Also, women kick ass. They become more confident and expressive. Men are attracted to that, which also shows up in dating after 40. We are incredibly attractive to younger men.

OREN: That’s true. And, although we become more discriminating, maturity also gives us the freedom to be a little less discriminating. I’m not looking for someone who can support me financially, for example.

MORE: What do we even mean by dating these days?

OREN: If you’re out with a man and you have a plan to spend time together, that’s a date.

ARMSTRONG: When you can say you’re on a date and the other person doesn’t look at you funny, you’re on a date. But the trickiest thing for women is to date. Women tend to be the Velcro of the universe. We pull up at a stop sign alongside someone and start a relationship. I try to teach women to enjoy an evening or an afternoon with someone; if you’d like to see him again, tell him he can call anytime. Then let it go. Go back to your life, and love your life.

OREN: It’s easy to confuse dating with the hope for a relationship. That hopefulness is like a third person on the date with you.

MORE: You’re talking about dating to date versus dating to marry?

ARMSTRONG: There are many valid purposes for dating. The trick is to know what yours is. Women will say, "I can’t date more than one man at a time." And I say, "That’s because you’re not dating." A woman attaches and feels it would be disloyal to go out with another man; then she ends up in a kind of serial monogamy. And the problem with that is that she’s not sorting fast enough. Finding your mate is not a finding problem; it’s a sorting problem. We need to experience more people and find out what we like and where we feel at home.

OREN: I agree. To sort, you have to be in the place of "I don’t know where this will go."

MORE: How do you get there?

OREN: Practice not believing the "blue sky" talk.

ARMSTRONG: That’s right. Did he say, "Would you like to meet my mother next Saturday?" If he didn’t say that, he’s just talking possibilities. This is absolutely critical: A man likes to picture a woman in his life in different situations, just for fun, then he says these pictures out loud. Women misunderstand. When he doesn’t follow up with real plans, she gets angry. She says, "Why are you saying your mother would love me when your profile is still up on"

OREN: But, also, men want to be the prince. They enjoy that process of seeing a woman swept off her feet. I live and date in Hollywood, which is great practice for fielding exactly the wrong stuff. Agents will say whatever it takes to get the deal closed. But when I was young, I would be swept off my feet, not realizing that they’re not bad guys, they’re just in the moment. In the moment, they want to be that guy.

MORE: Is believing the words the most common dating mistake?

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