DARE TO ASK: She's older? Ask her out, you stud

By PHILLIP MILANO, The Times-Union


What do others think about dating older women? I am intimidated about asking a particular woman out because I'm 23 and she's 38. Any suggestions?

Dustin, Houston


It's a great idea. We're always hearing about how older men score young babes, so prove it works the other way, too.

Jeff, 45, Victoria, British Columbia, Canada

Most women I know, myself included, hate the show-off kind. If you've known this woman a while and know her likes and dislikes, ask her to join you in an activity you both enjoy. A film festival or art gallery tour. Close to the end of the tour, film or whatever, ask her to join you for coffee or dinner. Don't push. If she is not interested, she will let you know.

Reesa, 37, Ellensburg, Wash.

Sorry Dustin, but unless a 38-year-old woman was looking for some hot sex with a young stud like you, she would not want to date you. I suspect you're interested in her for sex as well. What could you two possibly have in common other than sexual attraction? [But] take a chance. Just don't be hurt when she "hits it and quits it." Women are just as good at doing that as men are.

Rhonda O., 43, Laurelton, N.Y.

Experts say

We urgently sought out advice from Ivana Trump, ex of The Donald.

What? She's known for holding younger men in high esteem, and has an upcoming two-hour Fox reality special to prove it, so quit guffawing. In Ivana Young Man, she'll counsel a well-to-do older woman pursued by eight 20-something studs. When's the last time you were offered money to do that?

Through her publicist (we couldn't believe she got back to us, either), Ivana e-mailed to say Dustin should -- no, must -- go there.

"If you like this woman, then ask her out. She can only say yes, no, or even maybe. ... If she's terrific, and open, and happy with her life, she'll probably say yes and you both get a great evening out. ... Younger men/older women or vice-versa are nothing new or controversial anymore. The most important fact of life is that we live it, fully, daily and with no regrets. You've got a long road ahead of you, so get rid of the fear and trepidation, and as Nike tells us, just do it!"

Doing it they are. AARP The Magazine found that of 1,407 men and 2,094 women aged 40 to 69 it surveyed, a third of the women who date are going out with younger men.

"Older women are dating younger men because there are fewer men at their age level at this time in their lives," said Xenia Montenegro of AARP, who helped prepare the report. "You have to expand your market."

It doesn't hurt that older women are taking better care of themselves, and that changing sexual mores mean Baby Boomer lasses can now hook up easier with Gen-X or Y lads -- see Sex and The City and Desperate Housewives for specifics.

But it's not all about sex for older women. "They wouldn't mind having it, but they have more of a need for companionship, for someone who respects them," Montenegro said.

Phillip Milano, author of I Can't Believe You Asked That! (Perigee), moderates cross-cultural dialogue at Y? The National Forum on People's Differences. Visit www.yforum.com to submit questions and answers, or mail to Phillip Milano, c/o The Florida Times-Union, P.O. Box 1949, Jacksonville, FL 32231. Include contact information.