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Boomers’ Top Dating Questions—Answered


Not sure what to wear, whether to fudge your age, or even if you’re ready to get out there? Advice for these and other common queries are ahead.

By Nina Malkin

ating? At your age? Don’t make it sound like a disease you’re too old to get! Men and women in their 50s date plenty, whether just for fun or to meet a significant other. Granted, though, it can seem like a daunting prospect if you’ve been out of the game for awhile and are feeling a little rusty. So we’ve tackled the most common issues baby boomers are likely to confront in today’s singles scene. Read on for some very welcome advice.


How can I tell if I’m ready to date after a divorce or the death of a spouse?

When the idea of getting to know a new person feels like a good one—something you’d enjoy as opposed to something friends, family or society at large is pressuring you to do. “If thoughts of dating start with ‘I want’ rather than ‘I should,’ consider this a
Age means very little nowadays—relationships with disparities of a decade or more thrive.
signal that you’re ready to test the waters,” says Leah Klungness, Ph.D., a Long Island, New York-based psychologist and co-author of The Complete Single Mother. Maybe you’ve begun to notice more attractive people out there or have actually caught yourself (gasp!) flirting—two strong signs. And if you’ve started “just looking” at dating websites, you’re definitely getting there!


Should I fudge my age to seem more attractive to prospects?

Bad idea. “Honesty is the best policy if you care about your long-term credibility,” says Cathy Hamilton, director of BoomerGirl.com. If the person you’re dating turns out to be a good fit, you’d be living a lie, or would have to fess up eventually. Besides, since when does your age have anything to do with your attractiveness? “Real connection comes from mutual interests and passions, which often stem from shared recollections and similar world views,” says Klungness.

What are the best places to meet people I’d click with? I’m so over the bar scene.

Hamilton’s list is literally A to Z, from an art gallery to the zoo, and everything in between. “Go to real-estate open houses, lectures at the local university, the pool in your apartment complex, group golf or tennis lessons,” she says. “Start up a conversation over the olive bar at a health-food market.” The point is to try new things that interest you but also be open to opportunities in your everyday activities. “Take a bit of extra time to look your best when you go out,” says Klungness. “This will give you the added boost of confidence you may need to approach someone of interest.”

What’s appropriate when it comes to asking someone out? How long do you have to know someone before you ask him/her for a date?

Try not to impose rules or limits and just go with your gut. If you encounter someone interesting and the conversation’s flowing at a one-time-only event like a party or a gallery opening, go for it if it feels natural. If you’re likely to see this person again — at a class, say — wait it out a bit if that feels right. With online dating, you have the luxury of
Haven’t a thing to wear? Then it’s high time you found something by going shopping.
being able to email, then segue into a phone conversation and ultimately a face-to-face. No rush, but don’t wait forever either. Also remember that a date doesn’t have to be a formal, four-hour affair—getting together casually during the day is a great first date, so what could be easier than saying, “Want to grab coffee next week?”

I feel foolish approaching someone younger—how do I let him/her know I’m interested?

“The best approach, regardless of the age difference, is to smile, be yourself, and look for common ground,” says Klungness. Age discrepancies mean very little nowadays—relationships with disparities of a decade or more have been known to thrive. Of course, if the idea of asking out a much younger (or older) person makes you uneasy, don’t force yourself. “If you’re really hesitant to approach a younger person, you might be the one with the issues,” points out Hamilton. “Consider staying in your age bracket until you resolve them.”

After my long-term relationship, I’m just looking for fun, nothing serious. How upfront should I be about this on my date?

Let your behavior make your intentions clear. “As long as your actions and words are consistent with fun—no angling for a home-cooked meal, no pleading for help with household repairs—there’s no reason to make a big point of proclaiming time together as ‘no strings attached,’” says Klungness. Relationships are fluid, and you may change your mind about what you want as things progress. However, if your date makes it clear that he or she is looking to settle down and at the moment you’re not, let him or her know so as not to lead anyone on.

How do I tell my grown kids I’m starting to date?

True, they’re not toddlers, but this is a valid question. “Some adult children can only think of you as a parent, so they are unable to understand that you have feelings and needs apart from your nurturing role,” says Klungness. “Others try to discourage parents from dating to protect their inheritances or to keep some other family situation status quo.” But hey, it’s your life. Anticipate what your children’s reactions might be and how you’ll address them before you make any announcement, but don’t be afraid to put yourself first.

What should I wear on a date that’s attractive but doesn’t seem like I’m trying to look like my son or my daughter?

To avoid a ridiculous resemblance to your offspring, for starters, don’t borrow clothes from them. Just wear something you know you look great in — colors that flatter your face, cuts that show off your figure — without sacrificing comfort. It can also help to have an idea of what you’ll be doing and where you’ll be going so you won’t under- or overdress. Haven’t a thing to wear? Then it’s high time you found something by going shopping. “Take a friend your age whose opinion you trust and whose style you admire,” says Hamilton.

Who should pay for the date? Does anyone “go Dutch” anymore? Does anyone even know that expression anymore?

“Generally speaking, the person who does the inviting pays for the date, but don’t assume,” says Hamilton. Women should certainly not take it for granted that the man is in charge of the check—and if you’re a woman of some means it should be your pleasure to take someone out occasionally. If you’re not sure, though, at the end of the meal, pull out your purse/wallet and give your date a chance to insist that it’s his or her treat.

As a guy, what should I say if my date and I start to get intimate, and I have performance issues?

A sense of humor will take you far in this case—laugh it off and your date probably will, too. And since some women might worry it’s due to them, assure her that’s not the case. If the two of you are really clicking, you’ll be able to surmount this in time. With the miracles of modern medicine, where there’s a will, there’s a way!

Should I comment that it feels a little strange to be dating at my age?

It’s not necessarily bad to show your vulnerability, but surely there are other things to talk about. “Each of you will be having flashbacks to your sweaty palms at the 8th grade dance, and it may seem odd to eat dinner with someone whose underwear you did not purchase or who is driving a car you did not help choose,” says Klungness. “But these private thoughts are best kept to yourself.” She cautions against making TAPS — Talk About Previous Spouses (or Significant Others) — your theme song when trying to make a new start. So if you want to break the ice with a “This is a bit weird for me,” fine, but then move on.


Nina Malkin is the author of An Unlikely Cat Lady: Feral Adventures in the Backyard Jungle.
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