Finding The Courage To Date In Midlife

Can’t face the sting of rejection — or risk another round of heartbreak? Follow these eight steps to get over your fears and put yourself back on the market again in midlife.

By Jane Ganahl

y friend Cynthia — who’s pushing 50 and has never been married — recently told me that she’s been sitting on the shelf for so long now that she’s not sure what it will take to get her off of it again. “I never intended to stay dateless this long,” says the successful, attractive fine arts
I’m definitely more protective of my heart than I think I ever used to be.
photographer. “I think it started out as a reaction to having been hurt and needing to step back and try to assess what it was that I was doing wrong, where I was going wrong, or why things were failing so miserably for me on the relationship front. Maybe I was just plain burned out on dating.” (That was actually a few years ago.)

“It’s not like I’m opposed to dating, or finding a partner, or being in a relationship; I feel like I’m still open to these things in my heart of hearts,” says Cynthia, sighing. “But I’m definitely more protective of my heart than I think I ever used to be. And between my laser-sharp focus on my work and the fact that aging makes me more invisible to men, I feel like I’ve become something of a hermit! I’m ready to get out of my rut, but I think it would take an act of Congress to actually get back out there.”

My friend Tom (who’s in his mid-50s) is in a similar quandary. “After my divorce,” he explains, “I began to have a lot of female friends — as if to convince myself that I no longer needed intimacy. But now that I’m fully recovered from my divorce, I do want intimacy! I want to wake up on Sunday mornings in bed with someone wonderful… but I’m not sure how to get from here to there.” Like so many of my midlife single friends (myself included), Cynthia and Tom need a swift kick in the backside if they want to get back in the dating-and-mating game. The good news is that courage is a flexible muscle, and it’s totally capable of growing strong again…all it takes is a little exercise and willingness to take a few risks.

Understanding the risks — and rewards — of dating again
“To those people who are paralyzed by fear of being hurt again, I would say, come on — you’ve slain bigger dragons before!” laughs Bobbi Palmer, the self-styled “Dating and Relationship Coach for Women over 40.” “Compared to some of the challenges and tragedies faced by middle-aged singles — like the death of a parent or packing your kids off to college — risking rejection by doing a little online dating in an effort to find your soul mate can’t be that hard,” says Palmer.

Southern California-based Palmer notes that in several respects, dating is different for middle-aged people. First, the bad news: there are fewer dating candidates out there for midlife singles, because we are 10 times more selective than we were in our twenties. Now, here’s the good news: Singles over 50 spend less time fruitlessly searching for the right person, because we already know what we want — and aren’t willing to settle for less at this age. “Age provides us with both wisdom and fortitude,” explains Palmer. “Those two elements must be employed together if singles want to get themselves off the shelf and find love and romance!”

Eight steps for getting back in the dating game:
1. Know that it’s OK to be nervous, but start dating anyway. Fill out that online dating profile, say “hello” to the handsome stranger trying to pick out apples in the produce section, and tell your friends to set you up with someone. Accept that you’re scared, and understand that it’s normal to feel this way.

2. Decide your own pace for dating — and what you want to get out of it. Dating means different things to different people. Most people who’ve been taking a self-imposed hiatus might want to take things slowly at first, and when you do decide to stick a toe back into those waters, try to keep your expectations modest. An even better idea: Write them down! “I want someone to watch Mad Men with every week” is probably a more attainable short-term goal than “I want to meet my soul mate and get married within six months.”

3. Don’t let your children become an excuse for you not to date. Many people who fall into the 40-to-60 age range still have offspring at home. It’s possible that they will disapprove, but your kids need to understand that you also have emotional needs to fulfill. Kids living at home with you could provide all the excuses you need to shut the door on your own love life — but remember: You owe it to yourself to find someone special,
You owe it to yourself to find someone special.
and it could actually make you a happier (and better) parent.

4. Nix the negativity. Both men and women are guilty of talking too much about their most recent losses or frustrations — on dates and in the privacy of their own minds. If you start to hear that voice saying, “This is useless, I will never find anyone, I’m better off alone,” replace it with: “I usually get what I want, I deserve a great love, and I’ll take steps to get it.”

5. Consider changing what kind of qualities you’re looking for in a mate. If you’ve only dated people similar to yourself all your life, casting your net a little farther afield could improve the quality of your next catch. If you were married to a white-collar businessperson before, maybe that handsome carpenter or shy makeup artist would be a better fit for you today. Remember, you’re in the midst of reinventing yourself — and your dating life needs some shaking up too, right?

6. Look at any setbacks you encounter along the way as growth opportunities. If you really liked someone who didn’t ever call you again, rather than retreating back into your corner, ask yourself these questions: Was I authentic with this person? Did I practice kindness to my date as well as myself? And keep your perspective in a healthy place by reminding yourself that rejection is just a minor ruffle compared to what you’ve come through already in your life.

7. Remember that you’ll have to crack a lot of eggs to make the perfect omelet. A good rule of thumb to follow is that you need to date 10 people before you’ll find one that you might want to see as having the potential to become something more (and even that one person in 10 who seems wonderful may, in fact, have some carefully hidden baggage). Just know that you’re into this for the long haul, and don’t let yourself get discouraged during the process.

8. Keep your eyes on the prize. Stay focused on your goals, even if your spirit falters. “Whether your goal is to find everlasting love or to simply enjoy dating and find a companion, keep focused and try to shut out all the other noise,” advises Palmer. “Anything that is truly precious and meaningful in your life requires work and commitment, so remember: You can do the work, and you can get to your goal!”

Jane Ganahl is author of Naked on the Page: The Misadventures of My Unmarried Midlife, editor of the anthology Single Woman of a Certain Age, journalist of two decades, and codirector of San Francisco’s Litquake literary festival.
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