You’ve seen them. The ads in the Discovery Center catalog, that repository of yuppie activities. They proclaim “Party Mix: An Evening That Could Change Your Dating Life,” “Flirting–How to Do It Right,” “How to Take Charge of Your Single Life.” They promise to teach you how to “know the difference between romantic illusion and true love” and how to “learn from and deal with rejection.” And the name Gail Prince pops up in all of them.

“If you really want a relationship, you have to work at it, just like a career,” says Prince, a tiny woman whose spectacles tend to ride the tip of her nose. In a private consultation, the self-styled singles counselor and flirting expert is instructing me on the specifics of dating in the 90s.

Listening to her precise, slightly stern voice run through the differences between “datable” and “matable,” I’m reminded of a no-nonsense aunt. “You have to interview when you date,” she says. “Ask questions that will reveal your nonnegotiables.”

Creating a list of “nonnegotiables” is the first step in the Prince dating plan. Starting with categories such as education, intellect, sexuality, religion, and life-style, you think up characteristics you believe essential for a happy relationship. “When you’re conscious of your nonnegotiable characteristics, you’re out there dating with a whole different view. You’ve got on paper what you want, and that empowers you.”

The Prince plan comes packaged several different ways. Besides conducting the six-week class “How to Take Charge of Your Single Life” ($180) and “Party Mix,” an evening of “guided mixing through short dialogues” ($25) with clinical psychologist Basha Blumenthal, Prince has put out two videos “Flirting-How to Do It Right” and “Find Your Loving Partner”) and founded a singles board called the Friends of Leukemia Research Foundation. She conducts private consultations, which run $65 an hour. And she’s also known for her workshops at the annual singles event “Zazz Bash,” hosted by Sun-Times advice columnist Jeff Zaslow.

Prince got her start in the early 70s, when she was divorced and found there were no singles groups or programs. “I worked for the Mayer Kaplan Jewish Community Center to plan programs and they had none for singles. It wasn’t fashionable at the time.”

She ran a dating service through the community center for ten years before she was tapped to do singles columns for Inside Chicago magazine in the early 80s. After five years there Prince, who holds a master’s in education, decided to launch her own full-time consulting business. She currently sees between 75 and 85 people in classes and individual and group counseling sessions every week.

John, a 35-year-old architect, met Prince at the 1992 Zazz Bash and has been attending her sessions since last June. “Gail’s like an anchor,” he says. “How do I know what I’m looking for? She helps me identify those things. All the group members have homework so that we can contribute to the next session. Shell say, ‘Between now and next session, I want you to go out and get rejected.’ So many of us are afraid of that. She wants us to confront our feelings.”

Bonnie, a 41-year-old executive, says, “In our society it’s like you’re not quite right if you’re single.” But through Prince, she “actually began to think that being single is fun.”

In Prince’s worldview, “The two key words of life are consciousness and change. I went through a great part of my life unconscious, that’s why I had two divorces,” she says. “You can’t have change without consciousness based on what you haven’t gotten and what you want to get. I realized I can’t be in a marriage in the traditional sense, but I have a committed relationship of 14 years and my boyfriend and I are happy the way we are.”

David, a bearded 29-year-old high school teacher, joined Prince’s singles support group when he was 24. “I found Gail very early; I think I was in utero,” he says. “My job was very consuming and I realized I didn’t have a life. I learned communication and goal-setting skills. The group helped me process my feelings, see from another perspective, and separate illusions.” Prince’s influence is such that even though John managed to get married a couple of years ago, he continues to participate in one of her groups. “My wife doesn’t go, but she gets group sessions through me.”

Art accompanying story in printed newspaper (not available in this archive): photo/John Sundlof.