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

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."

For some people, she says the answer may be to join an organization where they are likely to meet others of their own age who may share some of the same interests. But the organization does not have to be a singles group where the express purpose is to meet someone as a potential marriage partner. Instead, mature adults may feel far more comfortable if they join a recreational or discussion group where they can get to know other participants before they make the move to ask someone out socially, says Carolee.

"One of the worst things you can do is wear your desperation on your forehead like a tattoo. Yet that is exactly what many people do when, ironically, the best way to connect with others is frequently not to appear obvious that you are looking for a social partner," the life coach advises.

Once you do identify someone you would like to get to know better, Carole recommends following one or more of the following steps to see where it leads:

1. Talk to the object of your interest as you would anyone else. Before you ever try to date the person, you want to get to know something about them and simple conversation is one of the best ways to do that.\

2. Don't immediately ask "red flag" questions such as "Are you married?" and "Would you like to get married again?" Some people hear those questions and immediately turn tail and run.

3. If initial conversations seem to go well, consider trying to get a small group of friends together that includes this person. This, Carolee says, is apt to work better than making an immediate jump from saying hello to "Let's date with an eye towards marriage."

4. If the other person indicates a particular passion for hobbies or events like bike rides or going to the movies, you can use this as a springboard by suggesting something like, "I haven't been bike riding in ages. Any chance you might like to go riding around the park this weekend?"

5. Don't fret about the fact that you look older than you did the last time you dated. If the other person is in your age range, they probably don't look 19 anymore either.

6. As you talk with the person, try to avoid falling into the usual traps of complaining about other romantic partners or ex-spouses. Once you do, you can already get the other person wondering, "Uh oh. If I keep seeing him (or her), what's going to get said about me?"

7. Listen as much as you talk. One of the big problems many nervous date partners engage in is paying far more attention to what they themselves say that they fail to hear what the other person is saying. The more you can keep initial conversations in balance, the more likely you and the other party may hit it off.

8. Don't press the other person into making commitments, especially very early in the exploration of a possible relationship. To some degree, as uncomfortable as it may feel, you need to see how things develop rather than trying to partner up immediately after you meet someone new.

9. If you're the type who often avoids small talk with anyone, be aware that you may be limiting your opportunities to meet and get to know someone new. Carolee says she hears clients complain they never meet anyone who, in social situations, do their best to keep everyone at bay without even realizing they do it.

10. Avoid assumptions like the other person isn't the right age for you, would not be interested in someone like you and, if they don't want to schedule a date immediately, won't be interested another time.