Something one of my clients said to me about learning how to start dating in your 50s really stuck with me. “Now that I finally have the time to devote to a relationship, I feel like no one has the time to give me.” I worked with that client many years ago, and her words still hold true today. Dating in your 50s is delicate, complex, and incredibly difficult to navigate. In this season of your life, you’re probably trying to tie up the loose ends. You’re right on the verge of retirement, your children are either newly fledged or about to leave the nest, and you’re settling into what the rest of your life will look like. On top of all of these major, transformative life changes, you’re ready for a relationship, which only makes your 50s even more overwhelming.
Here’s the part that few people say out loud: dating isn’t a 50-something’s game. Maybe you’ve been married for two decades and are newly single, or you never settled down because you were waiting for retirement. Regardless, the dating landscape has changed significantly since your 20s and 30s. I’m sure that you’re somewhat familiar with dating apps, but they’ve completely taken over the dating scene in the past 10 years. You might have used them in the past, but not only have they become harder to use, they’re now a breeding ground for hookup culture and casual flings! Online dating isn’t a viable way to find a long-term relationship anymore.
It’s safe to say that dating apps are nearly out of the question. So how are 50-something supposed to look for love? I would suggest using your circle of friends to help connect you with other singles, but most 50-somethings have small social circles. I know I’ve painted a negative picture about silver fox dating, but the reality doesn’t have to be that bad! Really, you just need to understand what you’re up against and learn how to approach dating over 50 with confidence and the right mindset. In my guide, I’ll unpack the biggest hurdles you’ll face dating in your 50s and share some of my best-kept tips for finding love in this season of your life.
Challenges of Dating in Your 50s
The truth is that there’s no one set answer for why dating over 50 is so difficult. Dating apps and online dating certainly add to the challenge, but more nuanced issues are at play, too, like stubbornness, independence, and lack of social spheres. I know it can feel like you’ve been thrown into a brand new world having to re-enter the dating scene at 50, and to some degree, that’s true! That said, you’re in good hands. I’ll touch on the challenges you’ll face dating in your 50s, but we’ll get into how to overcome them next.
Adjusting to New Dating Trends
Dating in your 50s can feel like stepping into an entirely new world, especially if you’ve been out of the dating scene for a while. The do’s and don’ts that shaped the dating landscape of decades past have all been transformed, and there’s an entirely new set of rules to follow! While most of these shifts in what’s acceptable with dating are positive, I’d argue that some have done more harm than good. If you’re not technically inclined and haven’t kept up with the latest gadgets, I’m sorry to say that modern dating is going to be tricky for you.
In the past two decades, dating apps and online dating have taken over the dating scene. Anyone unfamiliar with algorithms, swiping, liking, and creating online profiles is bound to face some initial roadblocks in our modern dating scene. Even most younger singles loathe dating app culture, but unfortunately, they feel like they have to use these platforms to have a chance at love. For most 50-something singles, online dating feels more like an obstacle than an opportunity! Dating apps are frustrating, full of date scammers, and often lead to superficial connections, which can make silver foxes feel even more isolated in the dating scene.
Most of my 50-something clients joined LUMA disheartened from being ghosted, falling into ambiguous situationships, or not being able to navigate the digital dating landscape. Trust me, I know the learning curve for online dating is steep. Figuring out how to make a stand-out profile, understanding private messaging etiquette, and determining the best pictures to use is understandably overwhelming. To top it off, dating apps are incredibly superficial, so anyone looking for a serious, loving relationship is going to feel like an outlier on these platforms. That said, there are ways to embrace dating over 50 without using any apps or algorithms, which I’ll dive into below. There are even dating apps designed for older singles that focus more on genuine connections over hookup culture and casual flings.
Balancing Independence With Partnership
Your 50s might just be the most independent decade of your life. You’re well-established professionally, financially, and hopefully, have worked on self-expansion, too! You’ve already built your career, lifestyle, hobbies, routines, and friendships, and you love the life you’ve created! For what might be the first time in your adult life, you’re comfortable, but that can also lead to rigidness. 50-something singles can be so comfortable in their routines that it’s difficult for them to make room for love.
One of my more recent clients was a 54-year-old gentleman. By most standards, he was the total package: handsome, kind, physically fit, and wealthy. He joined my Matchmaking services with the intent to find his “perfect compliment”, as he called it. Our biggest issue was that he wanted exactly what he wanted and was completely inflexible about his non-negotiables. He lived in a metropolitan area, but wanted to find a younger, conservative lady who didn’t want children. That’s already like finding a needle in a haystack, but here’s the kicker: he wanted her to live in a 10-mile radius from his condo because he didn’t want to drive far to meet her.
This is what I mean by rigidness. The truth is like anything else that’s good and worthwhile, love requires sacrifice. I explained to him that likely, he would have to choose one or the other: someone who matched all of his other non-negotiables, or someone in his neighborhood. Luckily, he chose the former, and is now happily married to a beautiful lady who was in another borough of his city. The moral of my story is that true love demands compromise. This might not be the situation you’re in, but sharing a life with a partner requires you to make room for them! You’ll have to change your schedule a bit, get involved in some of their hobbies, and include them in family gatherings. Integrating a new partner into your life doesn’t have to be a bad thing, either; it can be a force of transformation and personal growth if you shift your mindset!
Fewer Opportunities to Meet Other Singles
Have you also found that the older you get, the more your friends seem to disappear? This is something that happens to most of us, and I’m starting to notice it in my own life, too. I know it might seem malicious or intentional, but it’s more natural than we might think. Your friends who were once active in organizing community events or hosting dinner parties are probably just more focused on putting their kids through college and retiring. It’s not that they wanted to abandon ship, it’s they’re at the final chapter of their careers and parenthood, and they’re giving every ounce of energy to finishing strong.
Still yet, so many singles in their 50s feel forgotten by their old friends and like opportunities to make new ones are few and far between. Meeting other singles in-person might have felt natural to you 20 years ago, but now, it seems like an uphill battle. If you aren’t extroverted or haven’t prioritized expanding your network, the usual avenues for meeting people probably aren’t an option for you. With less friends, work events, and community gatherings on the offer, meeting other singles might feel impossible without dating apps.
I know this is can be hard to see, but it’s still entirely possible to put yourself out there and make new friends! This ties back into my point about being flexible, though, so you’ll have to move past any stubbornness in your routine. Joining hobby groups, attending local events, and checking out singles mixers in your city can help create organic opportunities for romance and platonic connections! You just have to be willing to let loose and have a little fun.
Family Dynamics and Responsibilities
I would argue that nothing shapes your dating experience like your children. By your 50s, your children might be out of the house or just about to leave the nest, but they’re probably adults. Despite them being grown, they’re still your babies, and of course they’re going to have strong feelings about their parent dating again! Especially if it’s the first time since a divorce or the loss of your spouse. These new dynamics between your established family and new partners is extremely delicate, and requires patience, understanding, and reassurance from everyone involved.
Here’s where things become convoluted: most people in their 50s are part of the “sandwich generation”, simultaneously, supporting their grown children and caring for their aging parents. I’m currently navigating this myself, and know just how difficult it is to be the one receiving the least support! Balancing these competing responsibilities can leave you little time or energy for dating, which just leads to more frustration. If you do try to prioritize dating, you’ll inevitably run into logistical challenges like scheduling, co-parenting, and caring for your parents.
The key to managing your already-established relationships and finding a new love is open, honest communication. You’ll need to get used to setting boundaries, establishing your priorities, and scheduling dedicated time for each person in your life. It’s a challenge, but it’s entirely possible to find the balance between family obligations and romance. Dating over 50 requires you to find a partner who understands and respects your lifestyle and who supports your relationships. It might take some time and perseverance, but the right person who compliments your lifestyle is out there waiting.
How to Start Dating in Your 50s
I know that dating over 50 can feel overwhelming and exhausting, but changing your approach to finding love will make your journey so much more fulfilling. My 50-something clients actually benefit from my relationship coaching sessions the most because they tend to enter the dating scene with negative assumptions and rigid expectations. You might think you have it all figured out, but I promise that there’s more to learn! The key is to find the balance between rigid non-negotiables and being reasonably flexible.
Use Dating Apps Wisely
If you’ve read any of my other blogs, you know that I’m not a big proponent of dating apps. Online dating generally promotes hookup culture, causes poor mental health, and singles rarely find serious relationships from these apps. Aside from that, not every dating app is designed for 50-somethings. Some apps, like Tinder U, are specific for college-age kids looking for casual flings. That said, there are a select few dating apps that are designed for singles over 50 who want something more serious. If you do decide to give digital dating a chance, just remember to take your time and have reasonable expectations.
Be Honest With your Intentions
In this season of life, honesty is definitely the best policy. Few 50-something singles are still sowing their wild oats and pursuing casual relationships over commitment. Even though your age group is generally on the same page about relationship goals, things can get messier when the conversation moves from exclusivity to major life changes like selling and moving homes. One of my more recent clients was certain she wanted to remarry, but she never wanted to share a home with a partner again. I know this seems a bit ironic, but it’s more common than you might think. Before you re-enter the dating scene, be clear on what you’re willing to compromise on for a new partnership.
Don’t Rush Blending Families
By the time you’re 50, your children have either already flown the nest or are about to spread their wings. Though their babies might be near grown, most 50-somethings are still helping their children get their footing in the real world. If you’re still semi-parenting your children, blending your families will be an inevitable step in your new relationship. It’s easy to want to introduce your new love to your family quickly, because after all, you’re head over heels for them and want to show your children how amazing your partner is! But blending families is a delicate process that requires patience, attention, and understanding. Instead of rushing into holidays and vacations with the whole family, let everyone get to know each other at their own pace so that no one feels pressured or even replaced!
Try Group Classes and Workshops
I know this piece of advice can feel a little flat, but hear me out: if you don’t have a large social circle, joining a new group or class is going to help you make new friends and meet potential partners. The reason so many dating coach suggest this for dating in your 50s is because it actually works! If you like swimming, join a swimming club or get a membership to a local pool. If you’re an expert oil painter, sign up for a workshop or even teach a class. Just being around people who share your interests will make new connections feel more organic, and hopefully, you’ll become more adept at your craft, too!
Let Go of Rigid Non-Negotiables
This is one of the hardest pills to swallow for 50-something singles. Trust me, I deeply understand that you’ve built the life you wanted and you’ve already had to make so many sacrifices to bring your vision to life. You’ve compromised so much already, how anyone ask you to do it again for a new partner? The truth is that while standards are important, being overly picky is limiting your chances of meeting someone incredible. Although I’ll be the first to tell you that compatibility is paradigm in a relationship, no one is going to check off every single one of your boxes. Before you start dating again, really consider which of your non-negotiables are necessary for you to be happy in a relationship and which can be reassessed.
Embrace Open Communication
You’ve likely heard this a million times, but it’s true: honest, open communication is the cornerstone for any healthy relationship. That can seem like an empty cliche, because I think most of us want to have vulnerable conversations, we’re just too afraid to really open up. I actually see communication issues the most with my 50-something clients, and I believe it stems from the fear of judgement or rejection. If you struggle to open up about your concerns or desires in a relationship, take the time to figure out where this fear is coming from. If you’re still hurting from a past romance, now is the time to heal that wound, not once you’re in a new relationship. I promise that the best partnerships are forged through emotional intimacy, which can only be gained through honest communication.
Get Involved in Your Community
I had a client a few years ago who wanted to find a partner, but was honestly a bit of a recluse. We had to work through his social anxiety before he started dating again, and I encouraged him to volunteer for a cause he’s passionate about. He started volunteering at his local animal shelter and became a beloved figure in his community. Admittedly, he did meet his current partner through my Matchmaking services, but his volunteering laid the foundation for him to be more outgoing and social! To prove my point, I will say that one of my dear friends met her husband by volunteering with Habitat for Humanity. Giving back to your community is really a win-win-win: you have a chance to do some good, you can relearn your love for community, and even find a life partner!
Attend Silver Fox Singles Events
Dating over 50 can feel like stepping into a minefield; few dating methods are actually geared towards your age group, and it’s extremely difficult to find an approach that aligns with your values. Luckily, there are dating events specifically designed for 50-somethings looking for real, lasting love. Of course, this is an easier option for singles living close to large cities, but even if you’re in a more rural area, silver fox singles events are more common than you might think. You might have to plan more for this idea, but I promise that it pays with interest. Age-based singles events are a much safer bet than approaching random people out in public. Everyone else at these events will have similar relationship goals, and they’ll all be within your age range, too!
Shift Your Mindset About Compromise
I know I’ve touched on this a lot already, but it’s worth diving into why compromise is both inevitable and beautiful. I’m sure you’ve heard the saying that nothing good is easy, and nothing easy is good. That is especially true with relationships. Any healthy partnership is built through hard work and sacrifice, but that doesn’t have to be a bad thing! Compromise doesn’t inherently mean settling or losing; it’s about finding solutions that work for both partners. Instead of fixating what you’ll have to let go of, consider what you have to gain from a compromise. For example, if you find a new partner and you both want to move in together, but can’t reach an agreement on which house to move into, consider starting fresh with a new home so that you’re both making an equal sacrifice.
Know That Good Things Come With Time
Much like nothing good is easy, good things usually come with time. If you’re wondering how to start dating in your 50s, this is my best piece of advice for you. I know how tempting it is to rush into a new relationship, but taking things too fast rarely leads anywhere good in the long run. If you hurry through the beginning stages of romance, you’ll miss out on one of the best, most passionate times of the relationship. You have to trust that all partnerships move at their own pace, and in good time! The right person is going to want to take things slow and get to know you over time, and if someone is trying to charge into a relationship too fast, it’s a huge red flag. Relationships that progress naturally are built on more solid foundations like trust, understanding, and genuine connection, so it’s worth the wait.
Why Singles Over 50 Choose Matchmakers
Did you know that most singles who use Matchmakers are between 40-60? Really, it just make sense: 50-somethings already know who they are and what they want from a partner, and they don’t want to waste more time endlessly scrolling through dating apps. They’re tired of other dating methods that aren’t designed for their age group and are looking for a more meaningful, curated way to find lasting love. They’re ready to invest in their love life and find a loving partner who’s committed to something real.
Professional Matchmakers don’t use apps and algorithms; they hand-select the most compatible matches for their clients. Matchmakers form extremely close relationships with their clients, which gives them deeper insight into what their client really wants from a relationship. At LUMA, we have Matchmakers specifically trained to help 50-somethings find lasting love and committed partnerships. Learn more about our membership options today to start your journey to find true love.
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