“Dating in your 50s is like picking through a curated secondhand store: there are desirable items in there somewhere, but you have to sort through a bunch of junk first.” This quote from one of my past clients still sticks with me to this day. Although my viewpoint isn’t as jaded, there’s plenty of truth in her metaphor, even if it is quite cynical.
Dating over 50 is delicate, complex, tedious, and extremely nuanced. By now, you’re probably on the precipice of retirement, dealing with your newfound empty nest, and finalizing the vision for what the rest of your life will look like. And perhaps, in the midst of these major life changes, you’ve found yourself single and looking, adding a new layer of complexity to the equation.
Here’s an uncomfortable truth that few people acknowledge: dating really is harder in your 50s. Whether you’ve been married for 20 years and are just now back on the market or you’re looking for a serious relationship for the first time, the dating scene has completely transformed since the days of your youth. I’m sure you’re familiar with dating apps, but have you ever been on one? If you haven’t kept up with technology trends, you might be due for a rude awakening trying to navigate the world of online dating.
Now, that’s not me trying to scare you; I’m just being honest. Dating apps have dominated the dating scene for the past 10 years, and they aren’t going away anytime soon. As their popularity skyrocketed, their model changed, too; online dating is now a breeding ground for hookup culture and casual flings instead of a way to find long-term partnership.
So, if dating apps aren’t a truly viable option, how are 50-something supposed to look for love? If you’re one of the smart ones who’s managed to keep a circle of friends, dating is going to be infinitely easier for you. That said, most 50-somethings let their friendships fall by the wayside long ago in the thrall of their career or raising a family. I know I’ve essentially painted a gloomy image of dating in your 50s, but I promise that it can be wonderfully fulfilling and fairly easy. With a little patience, understanding, and the right strategies, you can navigate the dating scene and find the love you deserve.
Why Is Dating So Hard In Your 50s?
Navigating Dating Trends
As I already mentioned, the dating landscape has changed entirely since your 20s and 30s. It can feel like moving to a country where you don’t speak the native language. The dating faux pas and non-negotiables that you’re used to aren’t in vogue anymore; the times have changed, and there’s a new dating rulebook to follow! Most of these new dating trends are helpful and positive, but others do more harm than good. Things like the 3-day rule no longer apply, but trends like ghosting and breadcrumbing are on the rise. Really, the dating scene just traded in its old problems for a brand new set.
Sherry, one of my recent clients, woke up to divorce papers laid out for her to sign on her kitchen counter. After 17 years of marriage, she found herself newly single (and deeply confused). She took the time to process her divorce, and once she was ready, re-entered the dating scene for the first time in two decades. Her first approach was dating apps, which came to an abrupt end after she was catfished by a date. Then, she tried meeting people out in the real world, but found herself struggling to understand modern dating.
After a year of trial, error, and more error, Sherry enlisted my help. Before starting her match search, I coached her through the do’s, don’ts, and what to expect in the modern dating scene. It wasn’t until she realized that things really had changed in the dating world since she was younger that we began to make progress. She discovered texting etiquette, dating safety, and intentionality. Now, this wasn’t an overnight change, but as Sherry became more educated on modern dating rules, she began to feel more confident in her own love life.
Once Sherry felt that she was fully equipped with dating knowledge and emotionally ready, we started her match search. Unsurprisingly, Sherry’s understanding of the dating scene gave her an edge that other women her age lacked. She fell hard for her third match, and they’re still together to this day. Here’s what I want you to take away from this: yes, dating is terrifying, confusing, and even unfair for 50-somethings. However, you’ll never win the game if you refuse to play. To find your own, unique edge in the dating scene, brush up on what’s going on in the dating world so that you can thrive.
Balancing Partnership And Independence
For most of us, our 50s are the first time we’re able to look up and catch a breath since childhood. Seriously, your 30s and 40s are so insanely stressful that you barely have time to process what’s happening. Now, coming into your golden years, you probably have true financial stability, are nearing retirement, and your kids are likely out of the house. You’ve already built the life you wanted, and now, you’re just coasting through on a high note. I’ve often thought of the 50s like the last two weeks before your high school graduation; this strange, yet comfortable liminal space on the edge of transformation. However, all of this newfound freedom brings a unique issue: most single-and-looking 50-somethings are too comfortable to make room for love.
I had a client, Abby, who was, by most standards, the total package: she was a successful, semi-retired business woman, feminine, but assertive, and ferociously intelligent. Oh, and did I mention that she was drop dead gorgeous? She joined my Matchmaking services intent on finding her soulmate, but was immovably unwilling to make compromises. Abby had a true laundry list of deal breakers and non-negotiables that made my job nearly impossible. For example, she refused to date someone who didn’t have black hair. Now, I can appreciate dark features, but making that an absolute must is quite frankly absurd.
Before we started her match search, my team coached her on reasonable standards versus impossible expectations. If you’ve read any of my other blogs, you’ll know this is something I talk about a lot because it is such a huge issue! After many months of what I’d consider low-level deprogramming, we finally made headway on recentering Abby’s expectations. One day, it just kind of clicked that her rigidness was the very thing holding her back. She revisited her laundry list, crossed off her most inane non-negotiables, and made space for love to find its way into her life.
With a new, healthier perspective, Abby asked us to start her match search. Shockingly, she developed a true connection with her first match, which isn’t common with Matchmaking. She married that match in Cabo a few years back. Here’s the moral of Abby’s story: anything good is hard work and requires sacrifice and compromise. Now, I know this might not be the exact situation you’re in, but most of my 50-something clients truly struggle to be flexible in dating. Many refuse to date other singles who don’t mesh perfectly with their schedules, lifestyles, or physical locations.
I’m not saying that you should settle for someone who doesn’t genuinely make you happy; that said, your best possible match probably isn’t in a convenient 10-mile radius from you. They won’t have the exact same routines, schedules, or lifestyle preferences. I know that change is scary, but it truly is the best driver of growth, learning, and self-actualization. Integrating a new partner into your life can allow you to see the world from a fresh perspective, making life feel more vibrant and fulfilling. All you need to do is shift your mindset from rigid, unbending fear, to open, vulnerable flexibility.
Less Opportunity For New Connections
A few years back, I realized that I’d slowly watched my circle of friends dwindle. I still had plenty of professional connections, but over the years, the girls I’d grab lunch and swap stories with seemed to fade into the background. This experience is something that most of us go through later in life, but hits 50-somethings especially hard. As people marry, have kids, and settle into their careers, weekends suddenly go from long nights out on the town to changing diapers and writing reports. It’s not that your friends wanted to fade into obscurity, it’s that life happens whether we like it or not. But now that you’re back in the dating scene wondering where to even begin looking for a partner, you might find yourself longing for the connections you once had.
George, a past client of mine, found himself in the same boat. He had been married for 12 years, raised 2 children, and ran his own small business. About a year after his marriage dissolved, George wanted to find a new romance, but seemed to hit a roadblock at every turn. Like Sherry, he tried dating apps first, but didn’t have luck finding women on the same page. He went to a few singles events in his city, but found himself feeling more isolated than ever. Once he’d exhausted all the dating options he knew of, he realized how much easier the entire affair would have been if he’d just kept in contact with his old fraternity brothers or coworkers.
See, having friends isn’t just about having a good laugh or travel partner; it’s about having a network of people you trust that you can call upon for help. That’s honestly the true essence of friendship: having someone to count on when your chips are down. George was alone in the dating scene, had tried every method he knew of, and had no one to turn to for help. If he had kept in contact with his past friends, they might have known another eligible single to introduce him to.
George eventually found me, enlisted my help, and found a wonderful lady to travel the world with. That said, George’s story could have been much shorter had he simply kept in contact with an old buddy. Dating as a 50-something is less of an uphill battle with the right people on your side! If you don’t have a good social circle to call on, now is the time to get out and make some new friends. I know how terrifying that can be, but really, it’s a win-win; not only will you have a little more joy and love in your life, but you’ll also have connections that can introduce you to other singles.
Managing Family Responsibilities
Does anything shape the human experience quite like having children? Sure, by the time you reach 50, your kids might already be out of the house or almost ready to leave the nest, but that doesn’t mean they don’t still play a major role in your dating expectations. Despite them being adults now with their own lives, it’s natural for our children to concern themselves with who we date. Maybe they want to look out for us, or maybe they aren’t ready to see their mom or dad enter a new relationship. Introducing a new partner to your children is a slippery slope that requires patience, understanding, and reassurance from everyone involved.
Stephanie, a past client of mine, was deeply conflicted about reentering the dating scene. Her marriage ended while her children were still young, and she spent nearly a decade as a single mother, fearing a new partner would disrupt her already delicate family dynamics. Once her children left home and started their own lives, Stephanie revisited her desire for a second chance at love. Still, though, she was afraid that her children wouldn’t accept that she was dating again, let alone a new stepparent.
Still conflicted but remaining hopeful, Stephanie joined my Matchmaking service to start her search for love. But before we started her match search, we really wanted to coach her through how to let go of guilt for desiring love. See, it wasn’t that Stephanie really thought her children would cut contact if she remarried; the heart of her internal struggle was that in the back of her mind, she felt guilty for wanting to move on. Some part of her believed that she couldn’t be the best mother if she was actively dating.
I think tons of singles, especially 50-somethings, wrestle with this negative mindset. I’m here to tell you that deciding to date again does not make you a bad parent! We’re quite literally wired to pursue love, and it’s something that no one should be ashamed of. That said, where things get a little tricky is introducing your new love to your established family. After a few months of coaching, we decided that Stephanie had reframed her mindset on dating as a single parent and was ready to start her match search. She ended up marrying a wonderful man who loves her children as much as he loves her.
So, how did Stephanie manage to pull off seamlessly intertwining two families? I won’t say it’s simple, but it’s easier than you’ve been led to believe. Blending families requires hard conversations, enforceable, but fair boundaries, and making each person in the equation feel valued every day. It’s definitely not easy, but it’s entirely possible to find your balance in this new dynamic. Dating in your 50s not only requires you to find a partner who understands your lifestyle, but one who also supports your well-established bonds. It might take some time, but the right person for you is out there waiting.
How Matchmaking Can Help
If dating in your 50s feels like playing a losing game, professional matchmaking services could be your best solution. A Matchmaker will only connect you with the highest caliber, most compatible singles who share your values, goals, and lifestyle. Matchmakers provide tailored, personalized support through date and relationship coaching so that you’re fully equipped to put your best foot forward in the dating scene.
Most importantly, Matchmakers can help you navigate new dating trends, connect you with singles outside of your social circle, and guide you on how to seamlessly blend families. We have Matchmakers who specialize in every preference, including Muslim, Christian, LBGTQ, and Jewish singles. Dating in your 50s certainly isn’t easy, but it’s far from impossible with the right tools, strategies, and expert support. If you’re committed to finding love but are tired of the complexities of modern dating, talk to us about our membership options today.
