Here’s the happy truth about dating over 50: Your long-married peers will probably be envious. Because at this age, you and your Gen X/Y cohort will have weathered children, financial reversals, second or third marriages, sexual drought, 3.5 different career paths—in short, lots of challenges. So, while being hunkered down in cohabitational bliss with your true love is great, real talk: How many people do you know that have that, really? Here’s to dating after 50 as a do-over, a love mulligan that has the potential to enrich your life experience. How to get that happening? We talked to a sociologist, dating app tech guru, single ladies and gentlemen and, yes, a matchmaker about best practices for dating over 50.

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1. Think About What You Want

Everyone—dating professionals to happily social singles—agrees: You’re more likely to have a pleasant dating experience if you spend some time envisioning what you want out of a date. One single Brooklyn man in his mid-50s with a teen son said he selected only women with children to ask out, reasoning that they’d already had children and wouldn’t be as anxious to start a family as women who had not had children. And Pepper Schwartz, professor of sociology at University of Washington and author of Dating After 50 for Dummies, suggests you pick five major qualities of a potential date as “must haves.” In her book, Schwartz lists 25 attributes (including intelligence, calm, thoughtful and great dancer) and suggests readers pick five to look for. Interestingly, she also includes a list of deal-breaking characteristics (things like if they’re a smoker, not interested in fitness or working) and suggests picking five of those to screen for.

2. Rehearse Your Meet-Up Banter

Stand-up comics have what they call a “tight five.” That’s five minutes of well-paced jokes and anecdotes that can reliably please an audience. Comics don’t so much prepare this to make the crowd happy; they do it so that they can get the first five minutes of a stage appearance down without freezing like a deer in the headlights or speaking into a silent void. The “tight five” helps the comic feel comfortable. Prepare your own ten-minute date version of this, a light and upbeat conversation that touches on your key interests and attributes (your work, kids, puppy, MacArthur Grant, the usual) while leaving room for your date to react and lead the conversation in another direction, if they like. Remember, everyone feels nervous meeting a new person, so the more engaging and pleasant you are, the better chance there is for everyone to lighten up. Even if your date can tell you’ve workshopped your dialogue, they will appreciate you made the effort. Dating coach Jennifer Wexler, founder of Find Real Love After 40, says that “when it comes to marketing themselves, women should be authentic upbeat and playful. They should share stories that highlight their unique personalities and interests. If a woman loves sports, she should share a short memorable story about an experience she had a particular game. She needs to include how she felt. It's important for a man to know what it will feel like to be with this woman.” Maybe don’t “work blue,” as the comics say: “You want to avoid being overly sexual,” Wexler says.

3. Make Friends With Technology

Dating apps are how people meet each other today: According to a 2019 Pew Research study, 30 percent of U.S. adults have used a dating app. However, of that number, only 16 percent of over-50s claim to have used a dating app. That shows huge potential for companies to serve the grown-ass adult market with new tech. “You should not be using swiping apps after 45,” says Adam Cohen Aslatei, founder and CEO of S’More, an app launched at the beginning of 2020 that within eight months has grown to 70,000 users in New York City, Boston, Washington, D.C. and Los Angeles. “Because by then, you’re more sophisticated. At the end of the day, you have to connect with the soul of the person, not so much with the lust.” S’More (named for people who are after “something more” than the usual dating experience) has a unique way of operating. In order to keep users from making snap judgements based on a selfie, you can review a series of icons representing a person’s interests that they have uploaded. Then, after texting each other a few times, you can video chat with them. And here’s the “anti-superficial dating app” special sauce: You talk to each other for two minutes with blurred screens. Only then do you get a look at each other’s profile photos. “Our product is like Love Is Blind,” Aslatei says, “getting to know a person before you see them.” Wexler says she finds that busy women appreciate the ease of online dating. “As an example, several years ago my friend, Carol, was busy with both a full-time job teaching and raising her daughter, so she didn't have time to go out and meet men. The online dating sites provided her with a great opportunity to communicate with many different men. At around midnight, after she finished grading papers and she put her daughter to bed, she would get on to Match.com and peruse the available profiles. It didn't take long before she met the man that later became her husband.”

4. But Think Outside the App, Too

While signing on to one or two dating apps might not seem like a lot of work, users report spending as many hours on the sites, responding to and making inquiries, as they would at a part-time job. That’s in addition to all the time and effort to craft an initial profile, as well as considering using a pro photographer not just for the initial profile shot but for updated shots as long your profile stays active. So that should keep you busy, but in addition to that, you’ll want to keep your eyes open to love connections in your daily life. (The Brooklynite we interviewed settled into a long-term relationship with a single mom from his son’s middle school after he noticed that she lived in his building.)

5. Consider a Matchmaker

“People are very intentional about dating right now, and working with a professional matchmaker can ensure that you’re meeting the quality of men and women that you’re looking for, says Callie Harris, senior matchmaker at Three-Day Rule. Not only will your matchmaker will do all the hard work of searching and vetting dates, but in practice, they keep the positivity flowing with perspectives to consider in order to make dating and meeting people more fun and less stressful. For example, Harris explained to us “dating can actually be really fun when there’s no pressure of finding a partner to raise children with—focus on the positives in your life (maybe you have more disposable income now or a flexible schedule).” Then again, you’ll need to make sure you’re on the same page with your matchmaker. We spoke with an Arizona widow in her early 50s with two young boys who visited a Jewish matchmaker who set her up with a man without children, which turned out to be a dealbreaker for her, since he didn’t understand how much time and attention children need. She ended up feeling disconnected not only from her date but also from her matchmaker, who she thought should have foreseen this mis-match, so she ended up not trying another match (and having the matchmaker waive her fee).

6. Be Upfront About Sex

Schwartz recommends you have “the talk” before you are in bed, in case you or your partner changes their mind about getting intimate. “Literally say: ‘Before we have sex, I want to talk about some issues that are important to me and also to tell you some things about myself that you need to know,’” she writes in Dating After 50 for Dummies. Among the topics you’ll want to cover are your expectations (or not) of monogamy, any physical limitations you may have and, of course, safe sex. Schwartz admits that you may feel awkward bringing up these topics but that broaching the topic actually frees your partner to disclose anything similar about themselves. Net effect, a free-wheeling convo actually helps diffuse any awkward tension around sex. Above all, try not to obsess over performance anxiety, she writes: “Very few people expect their 50-plus partner to be a sexual athlete.”

7. Consider Finances

Do you like mysterious English television shows with posh Brit landscapes? Check out Gold Digger on Acorn TV. In it, a handsome fortyish singleton Ben Barnes chats up diffident 60-year-old divorcee Julia Ormond in a museum and they start a torrid affair. But poor Julia Ormond can’t catch a break with her children and ex-husband convinced that the sexy chap is using their beloved mum and ex in order to luxuriate in her hotel suites and country manse. Which is…an expected-enough assumption that an television series is written around it. Apart from the judgement of others, consider your financial reality. What does your own financial situation allow? Do you have disposable income to spend on dates? Can you pick up the check for someone else, if they are not able to? Do you feel comfortable doing that? In matters of the wallet or matters of the heart, according to Wexler, “Women over 50 need to learn to ‘go slow and say no.’ It takes time to really get to know a man and they shouldn't rush into a relationship and they need to learn to say ‘no’ to any man or relationship that isn't right for them.”

8. Have a Feel-Good Date Look Ready

The whip-smart and lovely Kim France pretty much perfected the art of the seemingly effortless and cool outfit during her editorship of Lucky magazine. The 50-something writes on her blog, Girls of a Certain Age, that she tends toward “clothes that are just slightly sexy on a date,” usually a quality top from makers like Isabel Marant or a cami like this one from Nili Lotan and skinny pants from leather to denim. We’re also bullish on any of these can’t-miss wardrobe essentials for women 50+. Fashion for the advent of Zoom dating? We recommend you wear a shirt in a color that makes you feel pretty, with a cosmetic people wore prior to face masks called lipstick and no pants, because who cares? On second thought, S’More dating app CEO says that video home tours are a trend for new dates to learn more about one another, so maybe sticking to a skinny pair of sweats on the bottom is a workable compromise.

9. Build Your Resiliency Muscle

While going on dates can involve disappointment or rejection, Schwartz counsels to remember her theory of pineapple, which goes something like this—even though pineapple is regarded by many as delicious, not everyone likes it. (Schwartz herself picks pineapple chunks out of fruit salads she’s served.) “You have to be resilient,” she says. “Nobody likes everything, some people don’t like pineapple and some people don’t like me, it’s just taste.” More encouragement comes from Harris, who in her matchmaking days has seen—and made—lots of matches, so she speaks from experience. “Most everyone in your [age 50+] dating pool is on an even playing field,” Harris says. “If you think you’re the only one recently divorced and navigating unfamiliar dating territory, I promise you, you’re not alone!” And remember, you’ve got options. “Dating is about collecting information and at the end of the date if you decide that he's not right for you, then move on,” Wexler says. “No need to make him wrong. Don’t judge him—you wouldn’t want him to judge you.”

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