Dating After 40: How to Overcome the "I'm Too Old to Date" Syndrome

"I can't go on a date. I'm 40!"

My friend, Theresa, is like many women - and men - who have spent almost a generation of their lives in a marriage only to find themselves slightly past their youth, terrified at the idea of trying to re-enter the world of non-marital social relationships. Once our chins and chests begin to sag a little and our hips or waist thicken, the concept of flirting, let alone trying to find a new romantic partner, seems like a world that has passed us by.

"Dating is for twenty-somethings," says Marguerite, a newly single woman of 56 who first dismissed the idea of meeting another man altogether. Now, after more than 15 months since her divorce that ended a 32-year marriage, she hates the fact that her entire social circle consists of couples whom she feels do not understand what it is like for her. She is lonely, she admits, but feels completely overwhelmed and incapable of taking the first steps to meet someone else.

"The last time I had a date, I was nineteen and the rules all seemed pretty concrete," writes Marguerite in an email. "Now it's a totally different world. When I do meet a man who seems interesting, I find myself lapsing into silly girlish behavior because I don't know anything different. Is there some class I can take?"

Enter Carolee Woodward, a life coach from Southern California who works with a group that helps people over the age of 35 find their footing in the dating world they may not have participated in for more than a decade. Carolee has been there herself; when her husband of more than 25 years died suddenly a few years ago, she discovered that once she was able to move beyond the cocoon of grief, she lacked the skills necessary to so much as ask a man to lunch or dinner.

"I was a sad case," she laughs, reminiscing. "My daughter literally had to lead me by the hand and begin introducing me to men she thought I might like because I couldn't so much as say hello. When you're young, others are attracted to you easily. Once you have a few gray hairs and the last time you listened to a romantic song, Barry White was not only alive but practically a kid himself, it's plain discouraging."