Dating After Divorce: Why It’s So Intimidating and How to Know You’re Ready
For many people coming out of a long marriage, the idea of dating again isn’t exciting—it’s daunting.
Not just because dating has changed, but because it asks us to step back into visibility, evaluation, and uncertainty after years of having a settled relational identity.
This question is from Maya, who writes:
“I am newly single after a 15-year marriage and thinking about dating again. But can I first just say—yeah, no. I never thought I’d be dating at 43. So much has changed since the last time I dated, and I didn’t love it then either. I hate the idea of using dating apps, but my single friends tell me to just suck it up and join at least two different apps. According to my friends, at the very least, I’ll have some good stories to tell. I wasn’t particularly happy in my marriage. But, looking back now, I think I’d take my somewhat unhappy marriage over making a dating profile and then wading through profiles of men who might be married or bots or who knows what. I know this attitude is wrong for dating, but it’s how I feel. And I don’t see how it would change.”
Dear Maya,
I find individuals’ feelings about dating really fascinating, because they are so different from what most of us think we’re supposed to feel about dating.
What I mean by this is that if an alien were trying to figure out human mating rituals by watching a handful of the most popular contemporary rom-coms, they would easily conclude that it all starts with a charming meet-cute, an instant spark, and a sense of inevitability. They’d conclude that any awkwardness involved in this initial encounter is utterly adorable, not excruciatingly uncomfortable.
In reality, it’s far more common for people to feel a sense of dread and trepidation about dating rather than excitement and anticipation.
While some of this discord between the fantasy of dating and the reality can be blamed on dating apps, I think it also speaks to how uncomfortable it can be to put yourself out there and invest energy into potential relationships that may never go anywhere.
All of that is to say that you’re in very good company when it comes to not feeling enthusiastic about starting to date again. At the same time, as your friends’ attitudes toward dating show, it is possible to use dating apps and not totally hate every second of it.
From your letter, it sounds like you have friends who are standing by, ready to be helpful translators as you enter this unfamiliar new world of modern dating.
That’s great, because you’re about to discover—if you haven’t already—that dating today really is a different culture than the one you knew before, with its own grammar and its own customs.
It’s going to take some time to acclimate and find your footing. Your friends can be great resources for helping you think through the pros and cons of different apps, for crafting a profile that actually reflects who you are, and for sorting through potential matches to find ones that you genuinely want to pursue.
At the same time, you get to decide how you do this new dating thing, or even whether you do it at all. What works for your single friends really may not work for you. Listening to your own intuition along the way is going to be really important.
There’s no standard timeline for when to start dating after a marriage ends, and there’s also no standard for how much time and energy to put into dating.
Think of it like a zero-entry pool. You can sit on the edge and just dip your toe in. And you can wade up to your knees and then change your mind. Or you can jump in enthusiastically and get yourself into the deep end quickly if you want to.
It’s entirely your choice.
So now let’s talk about how to approach dating if you decide that you do, in fact, want to get your feet wet.
Rather than approaching dating as something weighty and serious, with potential long-term consequences for your future, what if you were to approach dating as an experiment instead?
This means keeping an open mind about the whole thing while you collect some data, like the ideal objective and neutral scientist. Question everything, even your own readiness.
Give yourself permission to change your mind at any moment.
Sign up for an app one day, take a look around, and let yourself delete it the next day if that’s what you want to do. In other words, unlike marriage, you really can change your mind on a whim and get out of it without a second thought.
While it’s true that some people can’t wait to start dating once a marriage ends, the ambivalence that you’re feeling is really common. Ambivalence is something to listen to and honor rather than trying to push your way through it in the hopes that if you make yourself do something, you’ll feel less ambivalent and unsure about it.
When you approach dating experimentally, you keep in mind that going out on a date—or even talking with someone on an app—is low-stakes and reversible.
Especially for those who’ve been married for a long time and are now newly single, I’m a big proponent of approaching dating as practice because it takes all the pressure off.
Instead of focusing on making a good impression on your date or trying to figure out if something has potential, dating as practice centers on your own experience.
You can ask yourself questions like, “What was that actually like?” or “Was I able to be myself?” or “Was there anything about this experience that surprised me?”
Questions like these are all about gathering information, updating your dating assumptions, and learning more about who you are as someone who’s single again. And because this is practice, you’re always free to stop, pause, or change direction.
There are no expectations you’ve agreed to fulfill—for yourself or anyone else.
Now that we’ve talked about getting into the right spirit for dating when you’re feeling ambivalence or even dread, let’s talk about the anticipation of what it will feel like to date versus the reality of what it may feel like.
When I work with individuals who are dreading putting themselves out there on dating apps, I always make sure to follow up after they’ve gone on a date or two and ask, “So, was it as bad as you were expecting it to be?” And what I hear consistently is something like, “No, it wasn’t. It was actually kind of fun.”
Interestingly, research has shown that while many of us believe that striking up a conversation with someone we don’t know will be awkward or unpleasant, we’re actually pretty much consistently wrong about that expectation.
The research I’m referring to was done by two psychologists—Nicholas Epley and Juliana Schroeder—who found that train passengers who were instructed to talk to a stranger on their morning commute reported more positive experiences than those who didn’t engage in conversations, even though the talkers predicted exactly the opposite.
Their work suggests that we often underestimate how pleasant it actually feels to connect, even briefly, with someone we don’t know.
This study illustrates why it’s so important to keep an open mind when you decide to start dating. Once you’ve taken all the pressure off the whole thing, all that’s happening is that you are meeting someone new and having some kind of experience together. That’s it.
While dating feels stressful and vulnerable, it’s helpful to remember that your date is also likely feeling awkward.
And realistically, even most bad first dates aren’t actually catastrophic in any way. They might be boring, or you may discover that you don’t have anything in common, or maybe there’s just no romantic spark. But you’ve made a potential new friend who’s introduced you to a fabulous new restaurant in your neighborhood.
As I see it, Maya, starting to date is going to offer you the opportunity to get to know people you didn’t know before.
Even more importantly, though, it’s going to offer you the opportunity to get to know yourself in a new way.
Dating after the end of a long marriage is not just about seeking a new partner. It actually marks a transition in your identity and a chance to discover who you are now, at 43 years old and single.
While the stability of a long marriage can hold appeal even when the marriage isn’t a particularly happy one, it’s also the case that a mildly unhappy marriage can result in a lack of personal growth and development for both partners, especially when the marriage is characterized by predictability and unchanging routines.
During marriages like this, when things aren’t bad enough to force an immediate change, it’s often the case that individuals not only lose interest in their partner.
They also lose interest in themselves.
What I mean by this is that while happy, vibrant relationships are characterized by inquisitiveness and engagement, unsatisfying relationships often deaden curiosity and interest.
It’s counterintuitive, but it’s often the case that dating after divorce sparks a re-engagement with our own personal development and a renewed interest in ourselves.
Getting to know someone else offers us the chance to also get to know ourselves better at the same time. Dating, especially at first, doesn’t have to be about finding the right person. It can just be about having new and interesting experiences and conversations, without rushing to conclusions or commitments.
None of this is to say that you should start dating, Maya. You can, and you don’t have to.
There are no wrong answers here, which means that you get to follow where your heart leads you.
And no matter where that is, you’re still free to change your mind and go in a new direction. There are so many areas of life—work, parenting, family—where we genuinely have responsibilities and commitments to keep. But casual dating isn’t one of them.
So let yourself approach this by first reveling in your freedom to do this your way.
And here’s my wish for you, Maya. May you trust yourself to know what’s right for you. May you give yourself permission to dip your toe into the dating pool or jump headfirst into the deep end. May you discover beautiful, surprising, and delightful things about yourself—and other humans—along the way.
~Angela
Ask Angela is an advice column dedicated to the topic of having fulfilling relationships after trauma. Click HERE to submit a question for Angela.
DISCLAIMER: this content is intended for informational purposes only and does not constitute professional medical or psychological advice, diagnosis, or treatment. Always seek the advice of your physician or other licensed health care provider with any questions or concerns you may have regarding a medical condition.
about angela Amias, LCSW
Angela Amias is a therapist, writer, and educator whose work focuses on healing relationship trauma and creating more meaningful, fulfilling connections. She has worked with hundreds of individuals and couples to help them understand how early experiences shape their relationships and to find a path toward deeper connection with themselves and others.
Her work is grounded in the belief that even painful experiences can become part of our growth, and that relationships can be a powerful place for healing and transformation.
Angela has been featured in publications including Today, Oprah, Cosmopolitan, Well + Good, The Independent, Salon, Inc., Forbes, Toronto Sun, Women’s Health, and Refinery29.
