October marks the beginning of cuffing season — the time of year when people actively look to find a romantic partner as the weather cools down. (It’s short for “handcuffing,” because you’re attaching yourself to that person for the winter.)
With fall rolling in and a chill in the air, you may be thinking about what you can do to increase your odds of meeting someone special. While you could conceivably cross paths with Your Person anywhere (On a plane! In a laundromat! On your doorstep delivering pizza!), you’ll be more likely to find love in some places than others — especially depending on the phase of life you’re in.
To that end, we asked experts to share their recommendations for folks at any age who are looking for love this cuffing season — or any season, for that matter. Here’s what they suggest and why:
In Your 20s
Myisha Battle, sexologist, dating coach and author of “This is Supposed to Be Fun”: “The best place to meet a romantic partner in your 20s is through school or friend connections. This is a naturally very social time for most people when parties and hangouts with diverse social circles can happen pretty organically and free time is more abundant.”
Blaine Anderson, a dating coach for men: “In your 20s, you’re often less confident approaching total strangers, so I’d lean in to activities and environments related to your existing social circles, where you can meet people who are only a degree or two removed from you — like an alumni football tailgate at the college you graduated from.
Or activities that singles naturally gravitate towards. Run clubs have gotten a ton of buzz recently for being hot spots for young singles — I’d check those out in particular!”
In Your 30s
Battle: “In your late 20s into your 30s, things are a little different because people tend to couple up and time may be more precious. People will be more likely to find partners through work, social groups like running clubs or political organizing, and [will be] making a concerted effort to stay open to meeting people if and when they have the chance to go out.”
Anderson: “In your 30s, you often have deeper friendships to lean on, plus you’re often more confident approaching strangers, so lean into introductions to your friends’ single friends. For example, your best buddy’s wife may have a handful of single girlfriends who would love to meet you, as long as you’re willing to ask!
[Try] picking up new hobbies and attending group events around them. For example, maybe you’ve been thinking about learning French — rather than doing it alone at home, find a French class at a nearby college. There might be singles you want to meet in class.”
In Your 40s
Battle: “In your 40s, the best place to meet a romantic partner is anywhere you enjoy spending time. Your priorities for partnership change in midlife and it may be difficult to make time for dating in a more traditional sense, especially if you have kids. Just be sure that you are making attempts when you can to be social, spend time in spaces that bring you joy and stay open to talking to people. This goes for all age ranges, but is particularly good for people 40 and up.”
Anderson: “In your 40s, you often have more resources, more flexibility with work and more specific interests. I’d recommend leaning into travel related to your interests and hobbies accordingly. So for example, if you’re really into pickleball, you could start training for a mixed doubles pickleball tournament in a destination you’ve wanted to visit.”
In Your 50s
Damona Hoffman, dating coach and author of “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”: “The challenge with dating in your 50s and up is that your social circle and routines are generally pretty set by then. This presents an opportunity, however, to find new activities and venues to connect with someone special.
“Active 50-somethings can make great connections in hiking groups, pickleball clubs and other intramural leagues. 50 is the new 40 and if you’ve still got gas in the tank, use it to meet another active single who wants to do thrilling things with you throughout the next season of your life.”
Jasmine Diaz, dating expert, matchmaker and founder of the Diaz Dating Group: “Trying to find a partner at a bar in your 50s is like playing Russian Roulette at the casino. Few people will share your vibe or hobbies, so social clubs are a great alternative. Whether it’s a hiking group, book club, travel group or an upscale club like Zero Bond, social clubs offer easy access to like-minded people.”
In Your 60s
Diaz: “If you’re looking for alternative ways to stay intellectually sharp, taking a class or attending a workshop is perfect for singles in their 60s. Language courses, cooking classes and art classes provide a low-pressure setting that fosters natural conversation. Forgo the traditional dating scene for something that aligns with your hobbies.”
Hoffman: “Many of my clients in their 60s are retired and using their newly discovered free time for two things: volunteerism and tourism — both great venues for meeting a potential match. Volunteering for a cause you care about connects you to people who share some of your values, and doing singles cruises or tours takes the guesswork out of vacation planning and presents an excellent opportunity for finding romance. There’s a reason that ‘The Love Boat’ lasted for nine seasons!”
In Your 70s+
Diaz: “Activity centers are a goldmine for finding your tribe. At 70+, it’s all about having fun and staying active. These centers provide weekly karaoke, trips, game nights, and classes that are curated for people in your age group. You will meet great people from various backgrounds and perhaps find a spark.”
Hoffman: “Dating apps and sites are hands-down the best way to meet someone in your 70s. It’s more efficient than asking for setups, joining new groups or approaching people on the street for older daters. Even though the technology can have a steep learning curve, once you’re online, you open yourself up to love. And not just in your local community, which might have more partnered people than singles in your age group, but anywhere in the world.”
The Big Takeaway
There was one recommendation we heard from several of our dating experts. While certain spaces are more favorable to folks in specific age groups, they emphasized that the best place to meet a romantic partner has less to do with age and more to do with your personal interests.
“No matter how old you are, you want to meet a partner who you have things in common with,” Anderson said. “This means you want to spend time mingling in locations related to your interests. For example, if you’re into health and fitness, and you’re seeking a partner who’s also physically fit and takes care of their health, group fitness classes like Barry’s are a much better option than bars.”
Single people of any age can benefit from joining a group that meets regularly or visiting places they enjoy on a consistent basis, Battle said.
“What people often have baked into their lives in their 20s — regular classes, activity schedules, seasonal parties, and friend groups close by — are harder to come by later in life,” she added. “It’s worth thinking about how you can build things like this back into your life and expand your community connections, as these tend to create opportunities to meet like-minded people.”
No matter how old you are, finding a compatible partner is about spending time in spaces that light you up and feel authentic to you, Diaz said.
“When you focus on trying to find someone rather than enjoying who you are, you will miss opportunities to create real genuine connections,” she added.