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Love & Sex

How to Enjoy (or at least not hate) Dating If You’re Over 50

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Let’s be honest: dating at any time in life is stressful and it doesn’t get easier with age.

Philadelphia psychologist Judith Sills, Ph.D., author of Getting Naked Again: Dating, Romance, Sex, and Love When You've Been Divorced, Widowed, Dumped, or Distracted, who remarried at 62, a dozen years after a divorce, will be the first to admit that. “While I understand that there’s a wish we could cruise through dating,” she says, “it’s normal and healthy to feel anxious, discomfort comes with the territory and you’ll be less angst-ridden if you accept that.”

Ken Page, LCSW, a Long Island, New York, psychotherapist, agrees. The author of Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy, Page married for the first time at 60 after what he describes as decades of chronic singledom. “I know what the pain of rejection feels like,” he says.

Sills and Page say there are simple steps you can take to decrease dating jitters and increase the likelihood of finding the intimacy you seek.

Befriend your longing for love instead of judging it. “We’re often told that we’re not supposed to search for love,” Page says, “and that it will find us when we’re not looking.” Forget that. “Instead, take a few minutes and write down why finding love at this time in your life really matters to you,” Page says. “It could be something like ‘I’m so much happier when I’m sharing my life with someone.’ Put this statement in your wallet or bag or on your fridge so you can remind yourself of why you’re going down this path when you hit a speed bump.”

Don’t focus on ruling people out. “While we want to make dating productive,” Sills says, “we don’t want to turn those early dates into an interrogation that’s all about uncovering whether someone meets your checklist.” Let yourself “experience” your date the way you experience your friends when they’re sitting across the table from you. “Even if someone isn’t going to be your true love,” she says, “he or she might still have a role in your life. They might become someone to bring to an event when you don’t want to go solo or someone who can recommend the best barbecue restaurant in town.”

Be yourself. Really. Forget all the dating advice that says to find your soulmate you need to make yourself more attractive and desirable, Page says. Sure, you want to bring our smartest and best self to the quest for love, but fixating on the ways you’re not “good enough” as you are is self-sabotaging. One, it makes you approach dating from a place of insecurity. Two, it leads you away from presenting your authentic self, which is essential to true intimacy.

Ignore the naysayers, including yourself, who say the romance clock has run out. “As a person who found true love late in life, I’m happy to say it happens,” says Sills. “People do find love and affection and all kinds of wonderful things at every stage of life. That isn’t to say it’s easy. I stayed in the dating world for 12 years and, yes, it made me crazy sometimes.”  Work at resisting doomsday negativity. “Do men only want younger women?” she says. “Not all. Are women only interested in rich men?  Not all. You’ll fear dating less if you acknowledge from the start that there are people you are going to find attractive who won’t respond to you.” But persistence pays off. “I am not young,” Sills says. “I am not thin. I am not rich. But I found my prince and I am happy.”

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