Dating Again? Nine Rules for Older Singles

Don't be afraid of dating when you're older. But do be careful. We have some dos and don'ts for senior daters.

older couple talking
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If you’re single this Valentine’s Day, you may long for a candlelit dinner with that special someone. The Golden Bachelor television series may have your head filled with visions of helicopter rides over Southern California and rappelling down a waterfall in Costa Rica. It can seem unfair if your reality is an array of dating apps that make you want to unplug and have dinner for one at your local trattoria.  

But dating for seniors doesn’t have to be grim or joyless. Indeed, 30% of Americans age 50 and older are single, according to the Pew Research Center, and many of them report enjoying the same feelings of infatuation and giddiness with a new partner as in their twenties and thirties. Indeed, because older adults know themselves better and are truly dating for companionship — rather than meeting someone with whom to start a family — they can be better positioned to successfully find the right mate. 

“It doesn’t matter how old you are if you meet someone and there are sparks and you fall for someone, it’s really fun,” says Harlee Beth Levy, 62, a divorced lawyer in Clarksburg, Md. “The sex is just as good. I'm more confident to just be myself.”

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That’s good news for the growing number of single or divorced older adults, who can expect to live solo longer. Over the last 30 years, the group with the largest increase in divorce rates was people 65 and older, whose divorce rate tripled, according to an analysis by Susan Brown, professor at Bowling Green State University in Ohio. 

Levy and experts on dating later in life recommend these dos and don’ts for dating at age 50 and beyond. 

1. Do understand yourself and your needs 

Levy notices that the older people she meets are very direct about who they are and what they’re looking for. On a phone call before an upcoming date, one man told her, “I do marathons. I go biking.” She could tell he was screening for someone with an equivalent level of energy. 

If you’ve just lost a spouse, through divorce or death, take time to get to know yourself before jumping into the dating pool, recommends Kerstin Rao, a dating mindset coach in Westport, Connecticut. “Take a realistic look at where you are in life, and what you wish you had done. This is your chance to reinvent within reason and to dream a little bit bigger than you gave yourself permission to, and a little more authentically than society taught you to dream,” Rao says. This assessment will help you understand why prior relationships may not have worked, and you can make a choice to move forward with less baggage.

2. Do be safe 

Dating has gotten riskier, so keeping yourself safe is the top priority. Read up on the dating red flags, from someone putting “roofies” (date-rape drugs) in your drink to “love bombing” new romantic partners by bombarding them with attention in order to manipulate them, or requesting money. 

“Scamming people, violent people and narcissistic people are highly motivated to fill their needs, and will deplete you and put you in danger,” Rao says. Many online daters use a video call to screen out scammers and incompatible partners before meeting up in real life — which should be in a public place.

Use protection before any sexual intimacy, even if pregnancy prevention is no longer an issue. Sexually transmitted infections among adults age 65 and older doubled in the past decade, according to the Centers for Disease Control. 

3. Do take it slow 

After a first dinner date with a man Janet Reeves, 51, met online, he suggested sitting in her car to continue their conversation. The divorced project manager from Fairfax, Virginia, got into the driver’s seat, turned to pull her door shut, and turned back to see her date had exposed himself. Reeves ended the date abruptly and spread the word among women in her area’s tight over-50 dating circles. Don’t be that guy. Take the time to get to know a potential new partner before initiating or agreeing to sexual intimacy.

Indeed, May Lee, 57, a broadcast journalist in Long Beach, California, believes one reason she and her fiance fell in love was the enforced slowdown of the pandemic’s early days. They got to know one another over long phone and video calls before meeting in person — socially distanced. “It was such a wholesome and honest way to get to know somebody,” recalls Lee, who has never been married. 

4. Do live a full life 

Levy, the Clarksburg lawyer, ended a 2½-year relationship this summer in part because her boyfriend didn’t have many friends or hobbies, and relied too heavily on her. Now she’s looking for someone who won’t resent her demanding career or the time she spends with her girlfriends and her 19- and 26-year-old children.

On the flip side, Rob Bywater, 55, an editorial director in Belfast, Maine, finds that he’s happiest when dating is balanced with real-life interactions such as volunteering, attending concerts and engaging in hobbies. “Dating is a barometer of my emotional state and my social life,” says Bywater, who divorced five years ago after a 15-year marriage. “If I'm spending a lot of time on the apps, that's a sign that I need to connect with friends and get out in the world.”

 5. Don’t stick to your 'type' 

As we get older, we know ourselves better and may realize that our youthful attractions stemmed from stereotypes, social pressure, or other superficial traits. Be open-minded about the type of individual you might date, what Rao calls “dating for character.” After her divorce, Levy realized that she’d always gone for tall, good-looking, masculine, dominant men — and therefore ended up with controlling partners and unequal relationships. She opened herself to dating less “alpha” men. 

She’s also discovered that it’s fine to date someone with baggage; after all, she has some too. A recent date shared some challenges he’d experienced with his grown child, which encouraged her to be comfortable that he wouldn’t judge her own parenting struggles, as past dates had done.

6. Don’t reinforce negative narratives 

When talking about your dating life, it can be easy to dwell on the failures: unsolicited sexual pictures, dates who ghost you or leave you with the check, and the like. This just feeds a cycle of negativity. “Keep that sense of humor, that sense of grace and space, or you will lose heart and get discouraged,” Rao says. “You slog through some pain and some self-doubt. All it takes is the one who is the right one.” 

7. Don’t follow outdated conventions 

Older daters tend to have financial and relationship commitments and may be set in their ways after living alone for years or decades. Don’t assume you’ll live together and share everything with your partner. Create the lifestyle and structure for financing, shared living, and health care that works for you as a couple. 

If you both have assets and financial commitments to grown children and grandchildren, it might make sense to keep your finances separate. Or perhaps you have one account for joint expenses and individual accounts for your separate responsibilities. Lee and her fiancé have been together for more than two years but are taking their time before deciding to live together or merge their finances. 

8. Don’t overlook the importance of life stage 

As much as you’re dating for the individual, the stage of life can be important too. Before committing to someone, consider how your health, lifestyles and needs will mesh, and discuss them frankly. A retiree who wants to travel the world may grow impatient with a partner who’s tied to a three-week annual vacation allotment or one who plans to attend all her grandchildren’s soccer games.

9. Don’t juggle too many partners 

When Levy first signed up for Match.com, she was overwhelmed with interest and ended up confusing different dates’ hometowns and professions in conversation. She had to take notes and make a spreadsheet to keep them straight. “It can be a little addictive and you could be checking it every day,” she warns, saying it’s better not to connect with too many people simultaneously.


Note: This item first appeared in Kiplinger’s Retirement Report, our popular monthly periodical that covers key concerns of affluent older Americans who are retired or preparing for retirement. Subscribe for retirement advice that’s right on the money.

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Contributing Writer, -

Katherine Reynolds Lewis is an award-winning journalist, speaker and author of The Good News About Bad Behavior: Why Kids Are Less Disciplined Than Ever – And What to Do About It. Her work has appeared in The Atlantic, Fortune, Medium, Mother Jones, The New York Times, Parents, Slate, USA Today, The Washington Post and Working Mother, among others. She's been an EWA Education Reporting Fellow, Fund for Investigative Journalism fellow and Logan Nonfiction Fellow at the Carey Institute for Global Good. Residencies include the Virginia Center for the Creative Arts and Ragdale. A Harvard physics graduate, Katherine previously worked as a national correspondent for Newhouse and Bloomberg News, covering everything from financial and media policy to the White House.