“Help! It’s My First Date In 20 Years”

Have no clue what to wear, or fear your flirting skills are a little rusty? Read this refresher course for a much-needed confidence boost.

By Lisa Cohn

or many people, going on a date fills them with a fluttery sense of excitement. But for Kelly Sklodowski, 42, a divorcée who’d recently ended a 20-year marriage that had left her feeling demoralized and undesirable, the prospect of meeting a new romantic interest for dinner triggered quite a different type of emotion: dread. “I was nervous, worried and scared,” admits the Mt. Laurel, NJ, native. “I worried about what to say, what to wear, and how much of my past I should talk about. Would we even be compatible enough to hold a conversation long enough to get us through the date?”

Kelly’s pre-date jitters are hardly hers alone. Today, one in four baby boomers — a whopping 16 million men and women — are now single, making them one of the fastest growing demographics in the country, says Judsen Culbreth,
Today, one in four baby boomers—a whopping 16 million men and women—are now single.
author of The Boomer’s Guide To Online Dating. And while some find the freedom of being back on the dating scene refreshing, it can also be scary heading into unknown territory. If you, like Kelly, are feeling like your dating skills are a little rusty and want a refresher course — and maybe a confidence boost to boot — heed our advice below. It was culled from dating experts and real men and women who took the plunge… and are loving it out there.

Remind yourself why you’re a catch
At first glance, the dating scene may seem a bit bleak for women in this age group. After all, aren’t men chasing younger girls to recapture their youth? That may be the stereotype, it’s hardly true across the board. These days, guys of all ages know that older women have a lot of unique things to offer. “The research shows there’s a new paradigm: Men are very interested in women who are successful,” says Culbreth. And that’s great news for women in their forties and fifties, many of whom are in their prime professionally. Stay-at-home moms who’ve raised wonderful children also win men’s admiration. “There’s something about the older generation that’s more nurturing,” adds Culbreth. “A lot of young guys are attracted to that.” Case in point: Judy Lederman, 46, who was married for 23 years, was pleasantly surprised how quickly she was swamped with suitors, many of whom were even in their twenties and thirties. “At first I wondered ‘Why would they be interested in me?’” recalls the New Rochelle, NY, native. “They all said, women in their forties don’t play games. They know what they want. It was a real ego boost! I felt like I was in Candyland.”

Give yourself a date-friendly makeover
Granted, women of all ages can spend inordinate amounts of time deciding what to wear on a big night out. But if you’ve spent decades out of the dating scene, it can be especially mind-boggling. You don’t want to look frumpy, but you also don’t want to don a baby tee and mini-skirt, either. “Don’t wear what your teenagers are wearing. That’s not who you are,” points out Tina Tessina, Ph.D., a psychotherapist and author of The Unofficial Guide to Dating Again. If your own fashion sense isn’t stupendous, turn to a friend who’s around your age for advice (it’s even better if your pal’s single, although a style-savvy married friend is fine too). That’s how Pat Smith, 43, from Denver, eased back into dating after 16 years of marriage. “I’m not this little young thing, but I wanted to look good,” she says. “At first, I thought maybe I should wear black because it would feel safe.” Her friends, however, coaxed her to try mixing things up color-wise. “So on my first date, I decided to wear a cute floral skirt with a black tank top — OK, I had to wear some black! — and a sweater draped over my shoulders,” she says. “It really helped to have a good group of girlfriends to help me through blind spots. They’ll honestly tell you if your butt looks big in something, or if you’re not wearing something that makes you look good or works with who you are, here and now.”

Tricks to keep the conversation rolling
During dates, nothing is quite as awkward as an uncomfortable silence. And it can be especially painful for people who feel their date-night conversation
After all, people love to talk about themselves.
skills are less than scintillating. While it’s tempting to fill the void by babbling, do your best to resist the urge. “When people are nervous, they’re likely to talk too much about themselves,” says Tessina. Instead, ask your date questions that are “non-me motivated,” she advises: “Stop thinking about yourself and think about the person you’re sitting with.” After all, people love to talk about themselves, they just need someone to lead the way—a fact that Kelly quickly found out during her first few dates. “I had fantastic phone conversations with this one guy, but in person he became nervous, which made me pretty tongue-tied,” she recalls. “So, when things got quiet, I asked questions to get the conversation going, making sure my questions revolved around things my date seemed excited about, whether that’s his job or recent vacation. And if things got quiet and he didn’t question me in return, I’d volunteer the same information back.” Using this trick, she was never at a loss for words.

Jump-start the fun with an activity date
If you’re meeting a romantic interest for the first time, it’s normal to stress over whether you (or your date) are having a fun enough, flirtatious enough time together. Luckily, there’s an easy way to make things more intriguing: by bypassing your usual dinner date and doing something a little more active, whether that’s meeting up for a game of tennis or taking a wine-tasting class. Pat, for instance, had great success inviting one date into her element: nature. “I met him at a popular trailhead to go for a hike,” she says. “I’m most comfortable in the outdoors and felt it was the best way to calm nerves and feel like there were fewer pretenses than sitting in a café. But there were plenty of other people around so I felt safe.” There’s another upside as well: Actions speak louder than words, so activity dates are great ways to get a handle on someone’s personality—which is what Judy found out by inviting one guy to go grocery shopping. “I like going to Costco on dates. You get to know a lot about the person without asking, like if they’re thrifty or impulse buyers,” she says. “In one instance, I found out my date eats healthy, like me. In the laundry detergent section, he even let slip that his ex-wife still does his laundry!” All in all, that’s info she’d have never gleaned otherwise.

Understand your intimacy limits
Having been off the market romantically for years or even decades, you may be wondering what’s changed on the intimacy front and whether your own sense of pacing is on par for the times. Do guys expect a kiss on the first date? And are people really having sex by the third? While it’s easy to get caught up in what’s “normal,” there’s no need to feel pressured. “Let your intimacy limits be what they are,” says Tessina. “If someone tries to hold your hand and you think it’s too soon, don’t get offended. Just say, ‘I’m not quite ready’ if you feel that way.” Or, if you don’t feel comfortable speaking up, there are plenty of nonverbal ways to establish boundaries. When Mary McCrary, 47, of Marshall, TX, first began dating again after 19 years of marriage, she quickly found some subtle tactics to stay inside her comfort zone. “When it became obvious one date was aiming to kiss me goodnight, I was uncomfortable as a fifteen-year-old and was thinking, ‘God, I hope he doesn’t put his tongue in my mouth!’ So I said ‘no’ by sticking out my hand for him to shake. He got the message.”

And maybe that’s a sign of the most important guideline for anyone re-entering the dating world—it’s all about doing what feels right for you, and not getting hung up on what you’re “supposed” to be doing. So get out there and enjoy yourself on your terms!

Writer Lisa Cohn is the coauthor of One Family, Two Family, New Family: Stories and Advice for Stepfamilies.
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