So, you’ve finally crossed over to the other side of the hill. You’ve either just retired or are only a few years away, so you probably have a sense of newfound freedom. If you played your career cards right, you have more disposable income now than maybe at any other point in your life. Being a 60-something on the cusp of true independence and financial perfection seems like an exciting time from the outside looking in. That is, of course, unless you’re single and looking.
Something most of my 60-something clients have in common is the fear that their best dating days are behind them. Most seem to think that dating over 60 is more like going to war than going out for a nice evening on the town. Trust me, I get it: the dating pool is getting smaller, which can make looking for love feel like finding a needle in a haystack. By 60, you might have mobility issues or other chronic conditions that affect your self-image and energy levels, making it harder to plan lengthy or active dates. If you do have health concerns, then online dating can seem like a safe haven, but you’ll soon find that dating apps are rife with scammers and bots trying to take advantage of you.
To top it all off, while you’re navigating the already complex web of dating in your 60s, you might be holding onto pain from your past relationships, which makes an already convoluted process even more challenging. So, we’re really left with one question: how are 60-something singles supposed to find a loving partner? I’m not going to pretend that dating in your 60s is easy. The dating landscape I described for you above is very real and very difficult to navigate. That said, all you need is a bit of understanding, self-compassion, and a few strategies to thrive in dating over 60. In my guide, I’ll detail the biggest obstacles you’ll face dating in your 60s and reveal some of my expert tips for finding love.
Challenges of Dating over 60
I wish I had a direct answer for you about why dating in your 60s is so incredibly challenging. Online dating and apps are arguably the worst perpetrators because few are designed for 60-something singles looking for real, lasting relationships. That said, more subtle issues are at play too like a shrinking dating pool and health concerns that might make some singles self-conscious. I know you might feel completely overwhelmed trying to learn how to thrive in dating over 60, but I promise that it gets better! I’ll cover how to master the dating scene, but first, we need to discuss the main challenges.
Smaller Dating Pool
One of the most disappointing realities of dating in your 60s is how small the dating pool is. The truth is that by this stage of life, many people are married, in long-term relationships, or have sworn off dating altogether. It can feel like the odds are stacked against you because there are so few singles in your age range that you connect with and want to date. If you’ve been married or in a committed, long-term relationship before, then you might feel even more discouraged.
This hopelessness drives so many 60-somethings to settle for a partner that they aren’t truly compatible with. Tons of my 60-something clients have told me that they’ll take anyone who agrees to go on a date with them because they’re that afraid of being alone. Recently, I had a 60-something client who was deeply frustrated with her dating pool. She was based in a very small, rural town in the northern US, and she knew just about everyone in her community. It took months of convincing her to expand our match search area to nearby cities. As soon as we did, she started seeing better matches.
Here’s the silver lining to take from that story: yes, the dating pool is smaller, but that doesn’t mean you should accept the first single guy or gal who takes interest in you. There are tons of eligible, desirable, and compatible 60-something singles out there, you just might need a bit more patience, strategy, and determination to find them! Your best match might not be in your hometown, and it’s completely normal to look beyond your immediate area for your true love.
Navigating Online Dating
I would argue that the biggest obstacle singles dating over 60 face is learning how to navigate dating apps. If you’ve been out of the dating scene the past decade, you might not understand how to navigate dating app interface, which makes digital dating feel like a minefield. Unfortunately, dating apps aren’t the unconventional, but fairly trustworthy platforms they used to be. Bots, scammers, and spam accounts are dominating dating apps right now, so keeping your personal information safe and determining which accounts are even real is harder than ever before.
I have a sad, cautionary tale to share about what happens when you take things at face value on dating apps. One of my current 60-something clients had a nasty run in with a date scammer before she found my services. When she was still on dating apps, she came across a profile of a man who claimed to be a famous singer from Ireland. She didn’t understand the dangers with online dating, and assumed that this profile was real. She chatted with this account for months before he finally asked her for a large sum of money to “come to America to live with her forever”. She wired him $10,000, and he disappeared without a trace. She was never able to get ahold of him again.
This incident destroyed her self-esteem. She said that she was too ashamed to tell her family what happened for months and that she swore off dating entirely for some time after being scammed. Eventually, she opened her heart back up to real love, and she joined LUMA. My team has since paired her with a wonderful, 100% real gentleman who’s neither a famous Irish singer nor a date scammer! My point is that trying to learn the intricacies of dating apps as a 60-something can truly feel like stepping into a warzone, and if you aren’t well-versed in dating and technology trends, you’re posed to lose more than you win.
Health and Wellness
In this season of your life, you’re lucky if you still have a perfect bill of health. Most of us start to experience chronic pain or other, more serious conditions by the time we reach our 40s and 50s, and these issues persist for the rest of our lives. Having health considerations that require a strict diet, a daily medication, or handicap aids might not have been part of the equation in your younger years, and makes re-entering the dating scene feel like even more of a challenge.
Trust me, I deeply understand how heavy health concerns can weight on your confidence. When I was in my late 30s, I was diagnosed with a condition that I’ll need to manage for the rest of my life. Luckily, I have my condition under control now and am in good health, but I know how hard it is just to maintain normalcy with chronic health conditions, let alone try to date! I’ve had clients tell me they’re afraid to put themselves out there because they worry about how their matches will see them. One of my clients even shared that she felt embarrassed about needing to bring a walking cane to a date because she was afraid it would make her seem less attractive.
But here’s the thing: true love looks well beyond the surface and sees who you really are. Anyone worth your time will appreciate the whole, perfectly imperfect person that you are. My best advice is to prioritize your health, but don’t let chronic conditions or physical aids hold you back from pursuing a real, lasting love. Embrace yourself as you are, and the right people will be naturally attracted to you.
Holding Onto Pain from the Past
Dating in your 60s usually causes scars from your past relationships to reopen. Maybe it’s the heartbreak of divorce, the grief of losing a partner, or the painful memory of the one that got away. These experiences shape how we approach relationships, and most singles in their 60s have trouble opening up to love again, afraid that history might repeat itself.
One of my clients went through a horribly nasty divorce that left her feeling unworthy of love. For years, she stopped dating altogether and was convinced that no one could truly care for her. She did finally muster up the courage to join my Matchmaking firm, but her first priority wasn’t to find love. Her sole prerogative was to heal from her past. After months of relationship coaching, we both felt that she was ready to re-enter the dating scene. Her confidence, self-assurance, and self-esteem had skyrocketed, and she trusted herself to make the right dating decisions. Today, she’s in a relationship with someone who makes her feel cherished, valued, and whole.
Just in case that didn’t resonate with you, I’ll use another, more ancient metaphor: holding onto pain and anger is must like holding a hot stone. The longer you hold it, the more it burns you. Eventually, you’ll have to set the hot stone down or it will destroy you hand. Why not take the steps today to rebuild and heal? The key is to acknowledge that your past experiences don’t define your future. With time, self-compassion, and the right support, you can let go of your heavy emotional burdens and step into the next chapter of your life with an open heart.
How to Start Dating in Your 60s
Dating in your 60s might feel disconcerting and exhausting, but it doesn’t have to be such an arduous journey. All you have to do is tweak your approach to finding love and maintain a positive, reassuring mindset. I know how easy it is to get caught up in a negative mindset about dating, especially if you haven’t had much luck with romance thus far. But in order to master dating over 60, you have to build you confidence, heal from your past, and go into dating believing that your best possible partner is out there, just waiting to meet you.
Heal From Your Past First
Most of us carry emotional scars from our past relationships, especially by the time we reach 60. Maybe you’re reeling from a nasty divorce, untimely loss of a partner, or regrets about choices made along the way. I know these experiences end up being heavy burdens, but they don’t have to hold you back from finding a new love. One of my first clients deeply wanted a new relationship, but was conflicted because he felt that moving on would somehow diminish the love he felt for his first wife. If no one else has given this to you, let me set you free right now: you have permission to make a fresh start and find a new partner. But first, try therapy or journaling to let go of your old wounds to create space for something new and beautiful to grow. Only a healed heart is ready to love again.
Reflect on What You Really Want
Dating over 60 isn’t about playing games. In this season of life, no one is applying outdated dating rules like waiting three days after a first date to call your love interest. Most 60-something singles know what they want, and you should, too! What do you envision for the next ten years of your life? Do you want an adventurous partner to travel the world with, or someone to cuddle up with on the couch? Take the time to really sit with these questions. Having clarity about what relationship dynamics and qualities you want will save you tons of time in the long run. When you’re sure about what you want, you’re more likely to attract it! Plus, knowing the qualities you’re looking for in a potential partner will help you know when a first date is worthy of a second.
Make Room for Imperfections
In that same breath I just told you to be clear about your expectations and preferences, I also want to encourage you to be flexible. Life leaves its mark on all of us, and by your 60s, those marks are part of your story. It might be a wrinkle here, an odd quirk there, or something more substantial like pain from the past. The beauty of dating over 60 is that perfection simply isn’t the standard anymore. Understanding that no one is perfect and that every single person has flaws will transform your dating life. Yes, you should have standards and non-negotiables, but reflect on which are necessary for your happiness and which might be holding you back from being loved by a perfectly imperfect partner.
Let Go of Social Expectations
If you let go of what society says you “should” be doing at this stage of your life, you’ll find true freedom. The truth is that dating in your 60s can be anything you make it! If you never ventured into hookup culture and you’re curious, don’t let society’s expectations hold you back from a new experience. If you want a serious relationship but don’t want to remarry, take pride in your decision. This is your unique journey, and only you can decide what’s best for you. Letting go of the pressure to conform to anyone else’s expectations will give you the power to create a relationship that aligns with your values, goals, and lifestyle. Remember: love doesn’t come with a rulebook, you have to make your own.
Adopt a Growth Mindset
By your 60s, you’ve lived through decades of life experiences, and hopefully gained some wisdom along the way. That said, just because you’ve reached your Golden Years doesn’t mean that there’s nothing left to learn, especially when it comes to love! Taking on a growth mindset is going to help you navigate dating in your 60s with more positivity and understanding. Instead of seeing rejection or a setback as a loss, chalk them up as opportunities to learn and grow. Maybe a first date didn’t go as you’d hoped or you’re feeling a little rusty after being out of the dating scene for a while. Don’t harbor on the negative; find a lesson from these challenges and use what you learn for your next date!
Be Open to New Experiences
I’m not one who believes in blanket generalizations or stereotypes, but having worked with hundreds of 60-something clients, I know that singles in their Golden Years are fairly hesitant to try new experiences. I had a client about 2 years back who wanted to find love again, but he flat out refused any first date suggestion other than this one restaurant he was a regular at. When I probed, he told me that he felt the most comfortable going somewhere he was familiar with. Eventually, I convinced him to break out of his comfort zone and at least let me plan him a date for a different restaurant! He hadn’t truly connected with any of his matches before, not knowing that his comfortability was making him come across as stale and boring. Once he agreed to meet a new match at a different restaurant, everything changed for him. He’s engaged to that match now!
Focus on Fitness
Generally, it’s just a good idea to stay active, fit, and healthy as you age. You’ll feel better, be stronger, and you might even meet new, amazing people, too! Sports like pickleball and tennis are designed to be played in a group, so get your game and on go make some new friends. If you’re more of a nature person, there are hiking or mountain biking groups just about everywhere in the US, so you should have plenty of options to choose from. When you take care of yourself, you naturally attract others who prioritize their health, too, you just have to go out and find your crowd. Plus, staying active and fit is a great way to boost your confidence in the dating scene!
Use Dating Apps With Caution
Dating apps can seem like a gift or cure-all, but I promise that they often do more harm than good. Sure, online dating can be exciting, but the emotions that often follow are frustration, confusion, and despondence. If you’re unsure about dating apps, it’s best to use them with caution. It’s estimated that around 30% of all dating app profiles are fake accounts, bots, or date scammers, so it’s crucial to stay vigilant and keep your information safe! That said, there are a select few dating apps specifically designed for dating over 60 that are easier to navigate and somewhat filtered for spam accounts. My best advice is to only have one dating app at a time, never spend more than a few hours a week on the app, and seek alternatives to dating apps when possible.
Try Singles Travel Groups
Imagine exploring a new city with a group of people who share you wanderlust and inspiration, and who just happen to be single, too. Yes, you could have a picture-perfect romance straight out of your favorite romance novel! Singles travel groups are one of my favorite ideas for dating in your 60s. There’s something magical and deeply fulfilling about experiencing new cultures, landscapes, and cities that makes every moment feel like romance. These groups will be filled with singles from all over the world, so you’ll have the opportunity to meet people you otherwise would have probably never connected with. Of course, if you do meet your Mr. or Ms. Right on a trip, you’ll have to keep the flame alive with regular visits and possibly relocation, which is all part of the fun!
Why Singles over 60 Choose Matchmakers
I’d say close to half of my clients are between 50-70, and it really just makes sense why singles in their Golden Years choose Matchmaking services. 60-somethings usually know what they bring to the table and what they want from a partner, and they simply aren’t willing to settle for less than ideal. They are done with the frustration and confusion of dating apps and want a more meaningful, human-centric way to find lasting love. They’re willing to invest in their love life to find their best possible partner who’s equally committed to a loving, lasting relationship.
Matchmakers don’t use apps or algorithms to find matches for their clients, they combine their intuition with their large networks of eligible singles to create lasting connections. At LUMA, we have Matchmakers specifically trained to help 60-somethings find lasting love and committed partnerships. If you’re ready to find your best possible match, learn about our membership options today.
Dating Over 50: Expert Advice From A Matchmaker
