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Dating Confidence Boosters for Boomers

Dating Confidence Boosters for Boomers
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By Nina Malkin

If you’ve got a date for Valentine’s Day — whether with someone new or your forever flame — the secret to making it special is feeling like a winner. But pre-date jitters don’t automatically vanish when you hit the mid-century mark. “Putting yourself ‘out there’ can be scary, especially if you’ve been through a divorce, loss of a spouse or a series of heartache,” says Florida-based life coach Casandra Henriquez, MPH ( “Negative self-talk and complacency can set in—the kind of doubts that kill confidence. But confidence is crucial on a date, because it shows that you know who you are, that you’re open to exploring new experiences and aren’t afraid of the possibilities.”   Ahead, how to psyche yourself up, neutralize your nerves and amp your attitude in order to stand out the next time you step out.

List your assets. You’ve lived long enough to acquire the qualities of a fun date and great mate—you just might not have taken inventory lately. Itemize your physical attributes first (great legs, warm smile, cute dimples, strong chin), then move on to the reasons why you’re a real catch (upbeat, trustworthy, understanding, funny). Write these reminders down, scan them before your date and never forget how true they are.

Practice flirting. Compliment the barista in your local coffee spot. Share a funny observation with your dentist’s receptionist. Catch a stranger’s eye while waiting for an elevator. Just about any random encounter can be an opportunity to sharpen your flirting skills—and the object of your attention needn’t be “age appropriate.” Just keep it light: You don’t want to give the wrong impression.

Hang with your fans. A day or two before date night, surround yourself with people who make you feel great about yourself. There’s a reason they love you, and their good vibes are sure to pump you up. Still skittish? Call your bestie on the way to your date—the very sound of his/her voice will feel like a pep talk.

Dress accordingly. Sure, you want to make his/her jaw drop, but comfort is the key to confidence so whatever you wear ought to feel great on. Rule of thumb: If it’s too tight, it’s not right. Err on the side of simplicity—forgo any outfit that screams “expensive!” or “sexy!” or is too fancy for the setting. Keep your scent and accessories subtle, too. That doesn’t mean be bland. Wear your favorite color to heighten your mood; a conversation piece will play to your uniqueness, and the interesting story attached can liven up any lulls in the chitchat.

Select the spot. A perk to being fifty-plus? Having a place where everybody knows your name, or at the very least, one where the lighting, seating and menu give you a sense of security. So rather than book a table at the hippest new spot in town, opt for home court advantage.

Connect with your inner hottie. Who’s the bombshell/badass you’d pick to play you in the movie of your life? Adopt a bit of that superstar’s mojo! Or invent an exciting dating avatar for yourself, complete with a sexy or exotic name. Goofy? Yes, but totally empowering.

Delve the romantic memory vault. You’re no teenager, but chances are you vividly recall your early days of dating. Choose a sweet/funny/sexy/cool reminiscence to share with your date, and encourage him/her to do the same. Not only will you bond over learning that you both wore Jordache, you’ll recapture a bit of that tantalizing “first time” magic.

See your success. Fantasize about how great the date will go, imagining yourself and your partner having fun. Visualization provides positive pictures for the mind that helps turn thoughts and feelings into reality.

Forget the world. If you keep looking around the room, you may start worrying that everyone else is hipper, sexier, younger, et cetera. So don’t poison yourself. Keep your focus on your date and yourself—end just enjoy!

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An all-around wordsmith, Nina Malkin is a journalist, novelist, copywriter and memoirist. She’s also an avid collector of lovely things from eras past—read her musings at