Dating Over 50: Advice from Matchmakers, Life Coaches and Gen Xers (Like Me) Who Have Done It

• A Guy with Mommy Issues: When I spoke to life coach Elizabeth Hudson, creator of the Sexual Alchemy podcast, she pointed out that a major red flag, and toxic combination, is when a man is "not fully in his masculine power of leadership and purpose," especially when the relationship is between an older woman and younger guy. Overall, Hudson recommends weeding out men who are looking for an authority figure or mentor instead of a lover. She cites the example of one client who dated a guy "who was looking to be 'Mommyed' to the point where she tried getting him numerous jobs (most of which he lost), and taking him on trips only to have him complain about everything." She says the dynamic tends to be untenable for a long-term commitment, but can be satisfying as more of a fun fling.
• A Fellow Who Competes with Your Family Members: Red flags to look for include when a date competes with a woman's teen or even grown children. For example, Hudson recalls one client sharing that her boyfriend asked, "Why did you get your daughter the açai bowl she wanted but won't take me to the restaurant I want to go to?"
• When Your Date Gives Off Opportunist Vibes: My friend Sarah regaled me with screen grabs of a man who she identified as a "Bitcoin scammer." Sarah says when she's chatting with men on the apps, she's noted a tendency for them to lead the conversation into topics of real estate investment and cryptocurrency. "No thank you," Sarah says, then cuts off communication, not wishing to turn into another chapter of smart women/scam stories.

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 when they were dating in their 30s. 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.

Takeaway: Create a private list of five must-have qualities and five deal-breaking characteristics and use it to screen for partners.

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. (Frankly, I like to do this before I go to parties and profesh networking opportunities as well, since it helps me skip past initial awkward silences. I think of the practice as coming up with the best Hinge prompts, but IRL.) 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, author 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.

Takeaway: Create an outline of topics you're interested in, touching on aspects of your life and work, so that you can be ready to converse with a date in a relaxed manner.

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. And 23 percent of people in their 50s have used online dating platforms. While millennials are experimenting with dating off apps and reports suggest Gen Z is killing dating apps, that still leaves a lot of grown-ass adults engaging with new tech. 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.” Another plus of using apps—it allows you a wide sample of partners to choose from, in order to better learn what you do and don't like. "I learned that some guys just want to text endlessly, or aren't willing to make an equal effort to make a plan," says single mom in her 50s Sarah. "I learned what my expectations are, and practiced setting boundaries."

Takeaway: Dating apps are worth trying, since they are convenient, widely used and can help narrow down potential behavioral likes and dislikes.

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.) Also, you heard it here first: We're in the midst of a speed dating comeback.

Takeaway: At the same time that you're crafting a great dating app profile, be open to blind dates, IRL meet-ups and speed dating, because you never know when romance can happen.

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).

Takeaway: Matchmakers put the time and focus into finding you a like-minded partner, but require clear direction (ie, your list of five must-haves and five deal-breakers from Rule 1. above) in order to come up with a suitable match.

Schwartz recommends you have “the talk” before you are in bed, or even start thinking about how to sext them, 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.”

Takeway: Broach monogamy, safe sex and other important topics before you start having sex.

7. Consider Finances

Do you like mysterious English television shows with posh Brit landscapes? Check out Gold Digger on Amazon. 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.”

Takeaway: Be honest with yourself about how much money you feel comfortable spending on your dates (and vice versa), and be willing to break off relationships that have economic inequalities that make you uneasy.

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,” and I'm always finding attractive outfit ideas from her. I'm also bullish on any of these wardrobe casics for women over 50. Fashion for the advent of video chatting? Wear a shirt in a color that makes you feel pretty, with a flattering lipstick and you're all set.

Takeaway: Have an outfit cleaned and ready to go that you feel comfortable and attractive in—it's one less thing to consider in dating.

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!” (In my experience, this applies to dating after 40, also.) 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.”

Takeaway: It's a numbers game, so don't take matches that don't move forward as failures and instead congratulate yourself for making the effort and learning more about your likes and dislikes.