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Dating at 20, 30, 40, 50 and 60

Dating at 20, 30, 40, 50 and 60

By Julie Taylor

There are certain things about dating that, no matter your age, remain the same, from the butterflies you feel when you meet someone cute to that painfully sweet moment when you exchange your first “I love you.” And yet, let’s be honest: there are also major differences between hooking up with someone when you are fresh out of college, looking for a mate during midlife, or finding a companion when you’re sixtysomething. Goals shift. Priorities change. To help you navigate each decade, we consulted leading dating and relationship experts to pinpoint the common desires and pitfalls of each age group — and got their advice on how to maximize your dating luck along the way.

Dating In Your 20s...

The post-college dating scene can often seem deceptively easy: after all, singles are rarely looking for a long-term commitment, as Katie, 25, from Oklahoma City can attest. “I’m not sure what I want out of life or a relationship,” she says. “When I date someone new, I’m not thinking about whether or not he’d be good husband material — I just wonder if he’d be fun to hang out with!” Even so, there’s a lot this age group can do now to make the most of their freewheeling days and pave the way for regret-free romance later in life. Some suggestions from the 20s set:
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Expand your dating horizons
Sure, twentysomethings date plenty of people but often get stuck dating the same type, says Andrea Lavinthal, coauthor of The Hook-Up Handbook: A Single Girl’s Guide to Living It Up. “You should definitely date as many different types as you can to get a good sense of what’s out there and to weed out the kind of people you don’t like,” she says. “At this point, dating is more about you than it is about the other person. You’re figuring out what makes you happy in a partner.”

Leave room for a love life
Dating often takes a back seat to career development for singles in their twenties. “They avoid relationships because they don’t want anything to derail their dreams,” explains Hannah Parmelee, M.S., of the Center for the Family at Pepperdine University. But blanket statements, like “I’m not dating anyone for the next six months/until I get promoted” can be dangerous, warns Lavinthal. “This closes off your possibilities, which is a bad thing — especially if the right person comes along in that time period,” she explains. So instead, make a conscious decision to give your love life a little TLC by posting your profile on an online dating site or accepting at least one date invitation per month.

Think twice before moving in together
Because finances are often tight at this age, it can be tempting to move in with someone you’ve gotten serious with romantically. But Parmelee says that cohabitation often backfires. “People end up getting stuck,” she says. “They slide into marriage not because they choose to, but because it’s just too hard to move out.” Tempted to move in together to save money? Move in with a friend instead and keep your dating options open.

Dating In Your 30s...

This is a time when many single people focus on finding The One, getting married, and having children, says Parmelee. But because this urge hits different people at different times (or doesn’t strike at all), therein lies the problem. “You either fall into that ‘Why I haven’t I found someone yet?’ mode, or you just don’t want to feel pressured,” says Lavinthal. “And when two people with opposing attitudes hook up, it can create issues.”

Set some mental deadlines
If you’re really set on getting married or moving in together and your partner just isn’t into it, Lavinthal recommends creating a timeline. “This isn’t something you need to share with your partner — but if you’d like to get engaged in two years, make a mental note of that,” she suggests. As you approach that two-year mark, evaluate where you are and where the relationship’s going. Talk about the issue. If your mate has no intention of getting married anytime soon but you’re still really into it, why waste any more time? “At some stage, enough is enough,” Lavinthal says. Likewise, if your partner wants to get hitched and you’re not ready, don’t give in to the peer pressure. “You have to do it when it’s right for you, not when it’s right for someone else,” she says.

Don’t get too set in your ways
Another challenge thirtysomethings frequently face is being too set in their ways, making it more difficult to embrace their partner’s habits. Jamie, 34, of Kansas City found this to be the case when she started dating Paul, 38. “He loved staying home and watching TV, while I prefer to go out,” she recalls. “At first, I went along with it, but before long, I was going crazy.” For this reason, compromising skills are key, says Lavinthal. “Agree to watch Family Guy with him if he’ll go to the gym with you. Just remember: You’re never going to change someone completely. If he’s a baseball junkie and you absolutely hate sports, remind yourself that he’s been this way for 30 years and the odds of him “growing out of it” are slim.

Dating In Your 40s...

Since approximately half of all first marriages fail, the fortysomething singles scene is flooded with divorced folks who are back on the market — with somewhat rusty dating skills. Or people who could be feeling ready for the “real thing” — if only they could find The One.

Brush up on your dating skills
If you’re dating after a split, ease into it, says Beatty Cohan, coauthor of For Better, For Worse, Forever: Discover the Path to Lasting Love. Make small talk with the person next to you in the grocery store line or go out on a “practice” date with a friend, asking your proxy to be brutally honest about how you come across to dates. You may also be way overdue for a makeover. “This doesn’t mean you have to get a facelift,” Cohan says, but it just might be time to trade in that 10-year-old pair of stonewashed, high-waisted jeans for a pair that actually fits.

Don’t date too soon after divorce
People frequently date too soon after a divorce, warns Parmelee. “They need to allow themselves time to heal and recognize how they contributed to the demise of their relationship before trying again.” That way, history is less likely to repeat itself, and they won’t fall into the same destructive patterns. To gauge if you’re ready, ask yourself these questions, suggests Judsen Culbreth, author of The Boomers’ Guide to Online Dating: Do you have an accepting attitude of the opposite sex — that is, do you not think all men are jerks or that all women are gold diggers? Are you engaged in activities and interests besides your work and kids? Do you believe you have control and can shape what happens in your love life? If you answered yes to these questions, then you may indeed have the right attitude.

If you have kids, proceed with caution
Don’t have time to date? Lean on friends, family, or qualified childcare givers for babysitting services, or schedule dates when your ex has the kids. But skip the introductions: “Never bring dates around your children until it’s serious,” Cohan advises. “Otherwise, you will simply confuse the child and bring up loyalty issues.” Even if you’re not introducing your dates to your children, however, you can tell kids, “You spend time with your friends, and I need to spend time with my friends, too,” Cohan recommends. Just remember you don’t need your kids’ permission to date. They might not exactly like the fact that you’re going out, but if you develop a full life without them, you’ll be a better parent.

Dating In Your 50s...

Many single fiftysomethings often feel like their dating days are over, having completely outgrown the singles events and club scenes that younger generations thrive in. Finding places where you’re comfortable meeting (and getting to know) people is crucial — and, according to our experts, well within reach if you take some small steps.

Don’t use work to escape intimacy
Because the fifties are often prime earning years, many singles this age use their work as an excuse to avoid intimacy. “I always tell my clients that when they’re on their death bed, they won’t say they wish they had spent an extra hour a day at the office,” Cohan says. “They’re going to wish they spent more time with their loved ones.” To jumpstart your dating life, look at it as another “work project.” Set goals — say, to spend a half hour per day on a dating site, or go out one night a week with a single friend — and meet them. Wouldn’t set foot in a nightclub? Try local volunteer organizations, a walking, running, or exercise club, or something else that feels more your speed.

Bridge the age gap
Many fiftysomethings may find themselves dating someone much younger. This doesn’t mean the relationship is doomed, provided you’ve picked the right person. “I’ve seen some May/December romances work well, as long as the younger partner is mature and sensitive,” says Culbreth. “You don’t want to be the parental figure or the paycheck. If that’s the dynamic that’s forming, get out while you can.” Culbreth adds that even though there is a “trophy wife” stereotype surrounding men and middle age, statistically men marry women within a three-year range of their own age. “Boomers want to be with someone who remembers the Beatles and when Kennedy was shot,” she says.

Don’t wait for The One to pursue your dreams
Holding off on buying a summer home, getting a pet, or taking that trip around the world until you find someone special to share it with? Stop waiting and start doing things for yourself, and love may magically arrive. That’s what happened for Catherine, 53, of St. Louis. “I used to wait for this knight in shining armor to save me,” she says. “But then I purchased a great house. I developed close bonds with my extended family. By the time I met my new boyfriend 18 months ago, I didn’t need anyone for the first time in my life — and that’s why our bond is so strong.”

Dating In Your 60s...

The golden years are indeed sweet: You’ve worked hard, and now it’s time to enjoy the fruit of your labors…only, with whom? “People this age tend to spend a lot of time complaining about being alone,” Cohan says. “But doing something about it is the only way you’ll ever change your situation. The mailman is not going to bring the perfect partner to your door. You’re going to have to take action to find that person!”

Get out there and meet people
Convinced you’re too old to mingle and meet new people? On the contrary, there are plenty of opportunities milling with single sixtysomethings just like you. Try churches, charities, volunteer groups, online dating sites, or classes at your local college in everything from pottery to ballroom dancing. If you’re on the shy side, convince a pal to sign up with you for mutual moral support.

Accept the changes that come with age
By this point, widowhood also becomes more common — and it hits hard. Most experts advise that recent widows and widowers abstain from dating for about a year — and to not be afraid to seek professional help with a therapist. “We all need a coach occasionally,” says Cohan. “This is one of these times when it’s important to have a professional on your side.” Bereaved spouses should try to avoid the common habit of putting their late spouse up on a pedestal. “When you choose to regard your late husband or wife as a saint, you can easily convince yourself that no one else will ever live up,” Cohan warns. “Try to remember the person as he or she truly was — warts and all,” and don’t be afraid to open yourself up to love again.

Julie Taylor dated in her 20s, married in her 30s and is anxiously awaiting her 40s and beyond.