It’s no secret that dating in your 40s is ridiculously challenging. It’s kind of like walking on a tightrope; one slight misstep on a date and you’ve blown your chances. By our 40s, most of us know who we are and aren’t still soul-searching for the missing pieces. In most ways, self-assuredness is a wonderful gift, but when it comes to dating, it can make us stubborn, inflexible, and unwilling to break out of our usual ways. You should know what you want in a partner, but most 40-somethings have extremely rigid non-negotiables that get in their way of real, imperfect love.
Here’s the other part of the equation: you’re no longer the same person you were in your 20s or 30s. You’re just a decade or two away from retirement, and although you can see the finish line, you’re completely bogged down in your career. You’ve got your kids from a previous relationship to love and nurture, plus your parents need more and more of your help Your priorities have shifted since the days of your youth as your responsibilities ask for more from you every day. When you combine all of those obligations, finding time to date in the midst of life’s chaos feels like an impossible challenge.
I know I’ve painted quite the gloomy picture about middle-aged dating, but it doesn’t have to be that bad. One of my 40-something clients told me recently that he’s never felt more authentic in the dating scene and that he’s more excited now than he was when he was 20. Why is his perspective so different from what I just detailed? My client has the right mindset about dating over 40 and is fully ready for a loving relationship! In my guide, I’ll unpack the biggest hurdles you’ll face dating in your 40s, and share some of best-kept tips for finding love in the most demanding season of your life.
Challenges of Dating in Your 40s
Before we dive into my best strategies for dating over 40, I want to address the biggest issues 40-somethings face in the dating scene. Learning how to start dating in your 40s is deeply nuanced and intricate. There’s no sole reason why middle-aged dating is so tumultuous; it’s a mix of demanding schedules, overcoming your past, being emotionally unavailable, and cohesively blending families.
Balancing Your Career, Family, and Dating
Oh, you thought you had it rough in your 30s balancing your career, family time, personal life, hobbies, and everything else? Welcome to your 40s, where free time becomes almost non-existent. By your 40s, you’re probably in the peak of your career with high-stakes responsibilities. You’ve reached a senior-level leadership position and every decision you make has rippling impacts for everyone above and below you! So not only do you have to bring 100% of your energy to work everyday, but you need to find another 100% for your family, friends, interests, and dating.
By this season of your life, you probably have children from previous relationships that are still living at home. Like any good parent, your kids come first! So when you aren’t preparing your next big pitch or presentation at work, you’re shuffling your kids between school and practice. All of these moving parts can make dating feel like a far-off, farfetched dream. To top it off, by the time you’re 40, your parents probably need your help around the house, getting groceries, and taking them to doctor’s visits.
Now, I’m not trying to make your 40s seem like a complete nightmare, but in all honesty, this decade is by far the most demanding. It’s easy to lose yourself trying to meet the needs of everyone else, so tons of singles over 40 put dating on the backburner. I wish I had all the answers, but I’m still learning how to be a 40-something myself. What I can tell you is that dating over 40 isn’t easy, finding a partner who can help you balance life’s responsibilities makes life all around better.
Cohesively Blending Families
One of the most delicate challenges of dating over 40 is creating an authentic, healthy, and functional blended family. We’ve all heard horror stories about step parents and step children, from blatantly ignoring boundaries to bullying and harassment. Finding a way to join two families together in a way that’s productive and fulfilling requires incredible empathy, compassion, and vulnerability, skills which most of us could use a refresher lesson on.
Just the thought of navigating blended families scares some singles away from dating over 40 altogether. I understand why; in many ways, being a step parent is even more difficult than being a parent. You’re not the main authority figure for your step kids and unsure how to navigate the line between fair discipline and behaving like an evil step parent. All of these intricate, fragile dynamics hang precariously by a thread, and one misstep could quite literally derail your relationship entirely.
That said, blended families can be the most rewarding dynamic by far. A few years ago, I had a client in her 40s with two teenagers still at home. She was so ready to find love again, but was terrified that changing dynamics would push her kids away. We introduced her to a widower with a young daughter, and the rest is history. All three girls are inseparable, and my client and her partner are now married. Blending families is a beautiful thing when done right, you just need a bit of love, kindness, and understanding.
Emotional Unavailability and Trust Issues
If you haven’t been through a soul-crushing breakup by 40, you’re in the select few. The average age people get married in the US is about 30, and first-time marriages last an average of 8 years. Most 40-somethings have experienced heartbreak, divorce, or another profound form of loss, each of which leaves emotional scars. I call 40’s the “jaded age” for relationships because so many of us are bitter about our past.
Losses like divorce aren’t just a one-time acute pain, either; they have profound, lasting, and usually negative effects on the way we view love, dating, and relationships. From my personal experience, 40-somethings seem to have the most issues with emotional availability, trusting others, and being vulnerable out of any other age group. It’s hard to watch, especially knowing that every 40-something client I’ve had deeply craves a new relationship, but is holding themselves back out of fear.
Emotional unavailability hardly ever stems from anger; it usually comes from a place of self-preservation. “I opened up in my last relationship and had my feelings used as ammunition against me, why would I try that again?” those words from a past client of mine still haunt me to this day. We were able to work through his negativity around relationships and find him a wonderful partner, but it took about a year of conscious mindset rewiring. I know just how tempting it is to hide yourself away from the world and give up on love, but I promise that overcoming your fear of being known pays with interest!
The Stigma of Middle-Aged Dating
Learning how to starting dating in your 40s feels like navigating a minefield. If you do things one way, you’re judged for it. If you try another way, you’re still judged for it. This is the part no one says out loud: the current dating scene is a young person’s game, and 40-somethings are judged for everything they do to find a partner. You’re cringey if you take a selfie for your dating app profile, but you’re weird if you don’t. But the stigma goes much deeper than how you date; singles in their 40s are often judged and shamed for being single in the first place.
One of the most pervasive stereotypes of middle-aged singles in that they’re desperate. I hate to say it because I fear it will only exacerbate the stigma, but we need to have an honest conversation about it. I have never had a client in their 40s who came across as desperate, but these misconceptions are so commonplace that it changes the way 40-somethings see themselves. Most of my clients in their 40s have negative self-image and self-esteem, which we have to work on before we start introducing them to matches.
The good news is that the middle-aged dating stigma is changing, and society is shifting away from the, “Why are you single?” conversation. The dating scene is constantly changing, and although usually for the worse, 40-somethings are becoming less judged and stigmatized for being single. If the biggest thing holding you back from dating in your 40s is the fear of being criticized, I promise that finding love again won’t be as daunting as you might think.
How to Start Dating in Your 40s
We all know that dating in your 40s is no small challenge, but the right mindset can completely transform your experience. Most of my past clients in their 40s felt impossibly stuck in their ways and overwhelmed when they first started dating again. They were so exhausted that they decided to seek out my help to take off some of the pressure and stress, and they ended up finding themselves in the process of finding love.
The truth is that our biggest limiting factors in love are the ones we create ourselves like unrealistic expectations, self-doubt, and holding onto pain from our past. I’ll show you what misconceptions and biases are standing in your way of true love, and how to overcome each obstacle to master dating as a 40-something.
Celebrate Your Age and Wisdom
So, life’s handed you the “learning how to date again in your 40s” card. You really only have two options: lean into your strengths, or let your weaknesses overcome you. Yes, by the time you’ve reached 40, you’ve left your years of youth behind. However, that does not mean that your age is a deficiency or some negative quality holding you back! Despite what society tells you, dating over 40 can be even more exciting and fulfilling than it was for you 20 years ago. Embrace your years, life experiences, and the wisdom you’ve gained as assets. It really is true that confidence will open doors for you, especially in the dating world.
Focus on Healing Before Dating
Rebound relationships are a well-known bad move, yet, in the emotional aftermath of a horrible divorce or breakup, we tend to not think rationally. I had a client last year who claimed he was ready for a new flame just 3 months after his wife of 20 years divorced him. We put the breaks on Matchmaking and worked on date coaching for a few months before I started his match search. He wasn’t happy with my decision at first, but during our last coaching session, he thanked me for “giving him stitches instead of a band aid”. Jumping back into the dating scene before you’ve fully processed the end of your relationship is only going to make for more heartbreak down the line.
Be Gracious and Patient With Yourself
I’ve often wondered if pressure around love, dating, and relationships serves any real purpose. Most of my past clients came to me with the notion that they had no choice but to rush into a new relationship. I get that watching your friends and family live picture-perfect lives with their spouses can feel like cosmic cruelty, but I promise that it’s better to wait for the right partner to come along than to accept mediocrity. Love isn’t on some set timeline; we find it whenever we do, never before, and never after. If you aren’t feeling any kind of connection with someone you’re casually seeing, it’s better to let them down easy than to try to build the life society tells you to on a rocky foundation. I promise, the right one will come along if you keep looking!
Take Your Time Blending Families
As important as it is to focus on the now, you should also consider what happens after you’ve found an amazing partner. If you still have children living at home, this is a bridge you’ll eventually have to cross, so it’s better to have a plan in place for when you reach it. My best advice for blending families it to take your time and don’t make the transition feel rushed or forced. Any relationship will naturally progress if given enough time, so I strongly suggest not moving your new beau in after only a few months of dating. Kids are sensitive, and you bring them in the mix before you and your partner are completely stable, it could leave a scar. If your new partner doesn’t respect you putting your kids first, they were never the right one for you anyway.
Let Go of Rigid Deal-Breakers
Around this time last year, I had a successful business woman as a client. She really the total package: financially independent, hilarious, charismatic, oh, and did I mention drop-dead gorgeous? But there was one thing holding her back in the dating scene: she refused to anyone who wasn’t named Alexander. I spent over a month breaking down her reason behind this standard, and finally got her to accept matches that weren’t “Alexanders”. She ended up marrying a “Dave” I introduced her to. Perfection is an insidious myth that only serves to hold you back. Be sure to look for the early signs that you and your date are compatible, but stop looking for someone who checks every nit-picky box and focus on finding someone who aligns with your lifestyle, goals, and values!
Don’t Pay Attention to the Single Stigma
This ties into my argument for patience, but I want to unpack society’s stereotype of being single over 40 a bit more. I’ve been a dating coach and Matchmaker long enough to know that most singles over 40 think their dating pool is full of “damaged goods”. I hate to use that word, but it’s the picture society paints for dating over 40. Here’s what society doesn’t tell you: most people get divorced in their 30s and 40s, and tons of those newly-single divorcees aren’t horrible, misguided people to stay away from. Most of them are successful, stable, and could make really amazing partners. I’m not saying that learning how to date in your 40s is easy, but there are wonderful potential partners on the market again, you just have to be willing to give them a chance.
Make the First Move
Anxiety often gets the better of us, even when there’s nothing to be nervous about. Contrary to popular opinion, people want others to make a move and approach them. Don’t believe me? A recent study by the American Psychological Association proved that most people want to be approached by strangers, but refuse to make the first move because they fear rejection. Not only is the fear of being turned down holding you back, it’s most unfounded. Don’t hesitate to send the first message, start a conversation with a handsome stranger, or ask someone out on a date. Other singles are waiting for you to be confident and take initiative, and you’ll never know unless you try.
Don’t Make Dating a Guessing Game
No one has the patience for mind games in their 40s. In this season of life, most people know what they bring to the table and what their relationship goals are. If you aren’t being open and honest about your values, ambitions, goals, and lifestyle, you’re setting yourself up for failure. Between balancing their careers, kids, and personal goals, singles over 40 simply don’t have the time or energy to mindread. If you think your date is putting out mixed signals, don’t drop hints about your emotions. Come right out and tell them so that you know if you two are compatible. Being vulnerable is a skill in itself, but the payoff is a healthy, long-term partnership.
Use the Right Dating Platforms
Dating apps don’t work for most commitment-minded singles, but I had a client who made them out to be a nightmarish wasteland. He said that he wasn’t suggested a single profile in a month! It turns out that he was using Tinder U, a version of Tinder specific for college students, by mistake. He deleted the app after joining LUMA and I matched him with wonderful women his age, but his story still haunts me. Not all dating apps are created equally! There are platforms for specific age groups, religious affiliations, hobbies, hookups, and serious relationships, so it’s important to recognize which apps are right for you. Take an inventory of your life and what aspects are the most important to you, and also consider whether you’re looking for a casual fling or a partnership. From there, you can narrow down the best dating apps for you. There are so many dating services for Christians, Muslims, the LGBTQ community, and every other group you can imagine!
Remember to Have Fun
Of course I had to save my most important point for last. If you’re dating in your 40s, I want you to remember that there’s a fine line between dating with intention and making your date feel like they’re being interrogated. I know dating can feel like a high-stakes interview, but try reframing it as an adventure. Dating over 40 is a great opportunity to meet interesting people, check out fun, romantic venues, and learn more about yourself, too. Let go of the pressure to find your perfect partner as quickly as possible and just enjoy the moment! Bringing a “I’m happy whatever happens” kind of energy to the dating scene is ultimately going to make you magnetic to great people.
Why 40-Somethings Choose Matchmakers
As a 40-something still navigating this stressful season of life, I know just how difficult it is to make time for anything, let alone dating. That said, I’ve helped hundreds of singles in their 40s actively date and find love while maintaining their other commitments. If you feel overwhelmed at the thought of re-entering the dating scene and want a dedicated expert who can guide you every step of the way, hiring a Matchmaker could be just want your dating life needs.
Matchmaking is designed to take the pressure, stress, and guesswork out of dating by matching you with elite, highly-compatible partners. Matchmakers are truly there for you with hands-on support and personalized date coaching to provide you with an easier, more fulfilling way to find love. At LUMA, we have Matchmakers who specialize in helping 40-somethings re-enter the dating scene and find lasting relationships without having to sacrifice hours of their time each week to dating apps. If you’re committed to finding your best possible partner, learn more about our membership options today.
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