Two generations kiss and tell

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Barbara Ruben

The first thing Andi Kay does when she gets home from a date is call her mom to dish on the details. Where did they go? Was he cute? Did he kiss her good night?

But at 42, Andi is no starry-eyed teenager. She's a divorcee and mother of three. And her mom, Stephanie Kay, also found herself single after a divorce, finally remarrying in her 60s.

"Andi and I both re-emerged as singles at times in our lives when we least expected to do so, and between us, we have 15 years of [post-marriage] dating experience," Stephanie said.

Over the years, the two have delighted over dates that seemed promising, and despaired over men who lied about being divorced or monopolized the conversation. One hadn't unpacked his boxes three years after moving into his apartment, while another failed to ask a single question about Stephanie.

So they decided to collaborate on a book of advice on dating for women in middle age and beyond. They named it after what they do best: Kiss and Tell: Tales by a Mother and Daughter.

"Mothers and daughters share clothes, jewelry, special moments and secrets. But few in past generations have shared dating stories as single women," Stephanie said.

Looking for love

In the book, the mother and daughter duo share stories from their own dating careers as well as ones they've culled from others, both as cautionary tales and examples of dating successes.

"All these guys I went out with they seemed so good at first, but there was always something wrong," Andi recalled. "One person was always late. Another constantly complained about his ex-wife. Then there's the guy who wined and dined me and brought me all those gifts. Then I found out he owed the IRS $50,000."

Stephanie, 69, a professional counselor with a practice in N. Bethesda, Md., lost her first husband to cancer when she was in her 40s, becoming a single mother to three teenagers.

She remarried, but divorced after six years. After a decade of dating, Stephanie met the man who would become her third husband.

Andi is a personal trainer who lives in Gaithersburg, Md. When her 10-year marriage was foundering, she decided to have a third child in an attempt to save it.

But instead, it only made her and her husband grow farther apart. They ended up divorcing. Andi is still single, but is in a promising relationship.

"After her dates, Andi would leave me these cell phone messages," Stephanie said, "and I'd be hysterical laughing. I knew a message under a few minutes was not a good date, but a four- or five-minute message was a good date. We exchanged stories and felt we had a lot to offer people," Stephanie said.

Sharing intimate details with her mother has come naturally to Andi as well. "I think we're very similar in a lot of ways, being in the single world as grown-ups. She doesn't judge me and I don't judge her, and I think that makes it easy."

The Kays aim their self-published book at women "because that's where our expertise is," but say that men can benefit from reading it, too.

One key finding for both genders is that humor can help defuse a tense situation. "One blind date, we got to the restaurant, and it was one horrible thing after another," Stephanie recalled.

"He spilled his wine. The dinner arrived late, and it was cold. And all of a sudden, we just started laughing about it, and that made it into a pleasurable thing."

So, what else can help a first date go right? Here are some tips the Kays offer in their book:

  • Be a good listener.
  • Keep your cell phone off.
  • Don't make a snap decision that he's not for you.
  • Don't talk about your ex.
  • Don't drink too much.

The Kays also address the difficulties of jumping back into the dating pool in mid-life.

"It's very scary when you haven't dated in a very long time. When my first husband died, I'd been married for 19 years," Stephanie said.

"No matter what age, you feel like you're being judged — on what you say, on how you look. As successful a person as you may be, you still feel this fear. 'What do I talk about? Do I offer to pay?'"

The dating landscape has changed in many ways for those whose last date may have been during the Nixon administration, including the brave new world of online dating.

"Internet dating requires abundant hope tinged with a healthy layer of skepticism," the authors say. Here are their tips:

  • Post a picture that is attractive, but really looks like you. After all, you'd be disappointed to find out a date looks a good decade older than the picture he posted.
  • For online dating contacts, get a free e-mail account that doesn't reveal your full name.
  • Be on the alert for married men, such as ones who don't post photos and who are evasive about where they live and work.
  • When setting a date, meet in a public place and tell a friend where you will be.

Intimacy issues of aging

There are also special issues for older adults when the date moves into the bedroom. Older women (and men) may be worried about revealing their aging bodies to someone new.

Here again, a little humor and even self-deprecation can go a long way. In the book, there's the example of Janet, 67, and Manny, 71. She was very nervous — and a little tipsy. Just as he was about to undress her, she blurted out, "Do you do fat thighs?" He laughed and replied, "Do you do hairy backs?"

But the increasing incidence of sexually transmitted diseases, in particular HIV/AIDS, adds some new concerns that sometimes aren't taken seriously enough.

"It's kind of finding your way again and determining what you feel comfortable doing. Only this time, the woman is the one who needs to make sure she brings along a condom," Andi said.

Problems also can arise when people's biases about age differ.

"I wanted to try to fix a man up who was 74 with a friend who was 62. He said, 'Oh no, she's too old for me,'" Stephanie recalled.

"Men who are comfortable with themselves don't need arm candy to stoke their egos," she said. "Some men think they're so hot, they have to have a young woman."

But it can work both ways. In the book, the Kays recount the story of Harriet, whose friends were concerned when she married an 81-year-old man.

Sure, he was in great shape, hiking and working out regularly. But at 81, anything could happen, they said. Did she want to end up as a caregiver?

Four months after their marriage, Harriet's back gave out, requiring major surgery. As soon as she recovered from that, she developed leg pain and needed a hip replaced, and her husband became her caregiver.

Despite all their dating dilemmas, the Kays believe in happy endings.

Andi herself met a French divorcee one day at the grocery store. He started a conversation because he remembered their kids had used the same school bus stop at one point. They are now in a long-term relationship.

 And while Stephanie said she never expected to marry again, after 10 years of dating, a friend set her up with a man in Atlantic City over a fourth of July weekend. They clicked and, after a long-distance relationship for three years, they married.

"This is my third marriage, and it's so wonderful," Stephanie said. We're so deliriously happy. I can't believe I could be so lucky."

Kiss and Tell: Tales by a Mother and Daughter is available at for $19.99 and at online book retailers, such as