Yes, You Can Flirt!

Expert advice for those of us who are returning to the dating world and are feeling a bit rusty.

By Sharon Edry

few months after my divorce over two years ago, I had an out-of-body experience. I was sitting in a neighborhood bar with some friends, chatting with a cute guy who was clearly interested in me. As I started to relax, feeling flattered by the attention, I also began to tilt my head, play with my hair and touch the man lightly on his arm.
I would stress out because I was worried that I was making a fool of myself.
Suddenly, I was watching myself from afar in horror. I thought, ‘What am I doing? Am I laughing too loudly? God, I haven’t acted like this in years!’ I was so embarrassed that I wanted to run away.

If you are recently divorced or have lost a spouse, facing the world of flirting can be an exciting but overwhelming experience that you haven’t dealt with since your days as a giggling teenager. “I didn’t even know where to start,” says Dina Sherman, 35, a divorced librarian from Brooklyn, New York. “I would stress out because I was worried that I was making a fool of myself or that I looked desperate.”

But uncomfortable or not, the playfully-romantic banter and lightly-sexual body language that create flirting — from eye contact and laughter to teasing — can be an important part of getting to know people in a fun, no-pressure way. “If you’ve ended a long-term relationship, then it’s hard to think about dealing with new people,” says Tina Tessina, Ph.D., a psychotherapist from Long Beach, California and author of The Unofficial Guide to Dating Again. “But pushing your comfort level a little bit — while taking it slowly — will help you redevelop your social skills.”

So, how can you fan the flirting flame after being out of the loop for so long? Here are some get-in-the-game tips:

1. Do what works for you.
Not everyone laughs loudly with strangers or wants to be touchy-feely when they’re flirting. If it feels more natural to just smile and ask some opening questions, try that instead. Losing her husband, Jeff, five years ago, forced Lisa Iannucci, founder of, to figure out her flirting style. “I’m not a giggler, except with my friends,” she says. “I just kind of step a little bit closer to show that I’m flirting.” Think about how you interact with your best buddies and what makes you feel comfortable,
The more you flirt, the less awkward you’ll feel.
says Tessina. If you’re tactile, she explains, you probably like to hug and touch people when you meet them, but if you’re more verbal, you may prefer to chat somebody up—not feel them up.

2. Build a social network first.
Instead of freaking yourself out by doing your first flirting at a bar full of strangers, start by finding an activity you like and join a group—such as a book club, a tennis league, or a charity organization. “It’s a safer way to start looking around and seeing if there’s someone you find interesting—and try out your flirting capacity with them,” says Tessina. “It’s easier when you have an idea of who these people are.” You’ll also have less to lose if the flirting fails, she adds, because you’ll still have lots of friends to hang out with.

3. Learn a lesson from Carrie.
Pretending you’re a TV or movie character — like Sex & the City’s Carrie Bradshaw — can help you develop a more flirtatious demeanor. “Watch some movies or television shows that feature flirting and copy what they’re doing,” says Tessina. “If you can pretend to be a character — not literally, but just sprinkling a few of her moves in here and there — it may get you past your reluctance and reticence.” So if you’re feeling slightly shy, slap on a sexy Samantha smile or try out Carrie’s sassy hair toss—you won’t have the background music, but you’ll break out of your old habits!

4. Practice may not mean perfect—but it helps anyway.
Dorothy Waldman’s initial attempts at flirting after divorce were, she recalls, “awkward and too businesslike.” The 56-year-old author and speaker from Houston felt painfully out of practice, but after a while, she learned from doing. “I started to develop some questions, some ways to break the ice,” she says. The fact is, the more you flirt, the less awkward you’ll feel, says Tessina. “You won’t actually see how it works for you until you start,” she explains. “You have to figure out how your assets work and what makes you feel good—and you can’t do that unless you practice.” Try just observing the first couple of times and watch what others do, she suggests, and then give it a go yourself.

Sharon Edry has written for Health, Self, Marie Claire, TV Guide, and The Los Angeles Times.
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