My 40s Life Blog

Dedicated to my dear friend, Catherine

It may be obvious, but I’ll just start by saying that dating in your forties with kids is nothing like dating was when you were in your twenties. 

First off, there’s the fact that we used to meet people in real life (IRL) back then and now, it’s all swiping on apps. When I was single in 2005, I cringed at my mom’s suggestion of trying out a dating website. Even though Match.com started in 1995, followed by Jdate in 1997, and eharmony in 2000, there was still a major stigma about online dating at the time. I had the perception that it was only for computer geeks. However, OKCupid came on the scene in 2007 with its in-depth questionnaires and compatibility matching and online [desktop] dating platforms slowly became normalized. 

Then, in 2012, Tinder changed everything with location based swiping apps on your smart phone. Fast forward to 2025, and now you can’t meet anyone outside of an app like Bumble, Hinge, or even Facebook. Meeting someone IRL over the produce at the grocery store no longer exists because no one looks up from their phones anymore! And, most organizations no longer allow you to date people from work so the organic ways that used to exist just aren’t there anymore.

So, there’s all that. Then, layer on the fact that you’re dating with children in tow, and now we’re faced with a whole new set of challenges when evaluating the dating pool. How can you flirt with that cute dad who isn’t wearing a wedding ring on the sidelines of one kid’s soccer game when you both have another kid hovering right next to you? 

When I was dating in my twenties, 30 seemed like a big milestone age for men. I firmly believe your twenties are for discovering who you are and what you want in life as it relates to career, family, adventures, and so on. Your frontal lobe finishes developing around age 25 and you’re better able to make smart choices, be planful, and regulate your emotions. Women often hear their biological clock ticking loudly in their twenties and feel a sense of urgency to meet someone and procreate, but many men still yearn for freedom and exploration during this decade. Both sexes are likely also highly focused on building their careers. In my experience, once they turned 30, men seemed more ready to settle down and commit to a relationship that could ultimately lead to building a family.

Now, 50 seems like that next milestone for dating, but for most relationship-minded people, it’s following the end of a first marriage. For many people, kids are in their teens and demand (and/or desire) less attention from parents. Careers have become well established. Mid-life crises are, hopefully, being worked through.

Ideally, you want to find someone who has already addressed their childhood traumas and the traumas that came from the end of their first marriage (if they had one). Of course, this is always a work in progress, but people need to make peace with their past, otherwise, it keeps coming back to bite them. Compatibility with their ex (assuming they have one) is ideal, but not always possible depending on the circumstances around the separation. 

Do you know someone who you think is a catch and just can’t figure out why they’re still single? Well, unlike in your twenties when the world was your oyster and there were plenty of fish in the sea, the dating pool of well-adjusted, attractive, single parents in their forties is more like a tiny puddle. I swipe right for every 50+ left swipes. It can be exhausting and, frankly, a little depressing. Not only can it be incredibly hard to find someone you’re attracted to, but then, as you get to know the one person you’re interested in, you may stumble across something else that’s a total showstopper.

If you are a monogamous relationship minded person, there are so many red flags to look out for – people who are still married, narcissists, incompatible attachment styles, mother/father wounds, incompatible conflict styles, and more. If all this is unfamiliar territory for you, see my reading list post for some books I recommend that really get into the meat of it.

What lures us in is different for everyone, but it all starts with attraction. I struggle with the superficiality of this because there are lots of reasons to love someone. I believe the most important qualities are what’s on the inside – someone’s character, what lies in their heart and head, if they are kind and considerate.  And, let’s be honest, no one in their forties and fifties looks as good as we did in our twenties, but you still have to want to kiss someone. If I’m not interested in making out with someone in the early days of dating, how will we sustain physical intimacy long-term when we’re older, not as firm and fit, have even more wrinkles than we do now, and way less hair?

A matchmaker once tried to convince me that a guy I was not the least bit attracted to could grow on me and I adamantly objected. I’m not interested in someone growing on me like mold on cheese. I want chemistry – a spark of excitement and desire! Always have. I’m just being true to myself and that’s the most important thing. Anything else would be settling. And, no one wants that.

Of course, the butterflies will fade and the relationship will evolve into a more comfortable friendship (see my 3 Stages of Love post), but please don’t keep seeing someone that doesn’t excite you in some way. One of my favorite Steve Jobs’ quotes is, “If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on.” Not everyone has experienced what this kind of love feels like, but I found it with my husband and once you’ve known that kind of love, you won’t accept anything less. Trust me, it’s worth waiting for.

So, in 2017, at age 39 when I found myself single again after my husband passed away unexpectedly, dating apps were the primary means for meeting new people. I constantly remind myself not to settle since it’s so easy to get discouraged in a world of endless swiping when no one seems to quite fit the idea of what you’re looking for. Or, they do, but then there’s a big, deal-breaker obstacle. It doesn’t matter how much you love someone or how attracted you are to them. There are legitimate deal-breakers that most are unwilling to compromise on. And, if these things mean that much to you, then you shouldn’t compromise.

The major deal breakers I have come across are kids, religion, politics, where you want to live, your attitude about work, your health habits, and vices. Some things can be worked around depending on how strongly one feels about their virtues. But, there’s no compromise if one person doesn’t want to have kids and you already have them. 

Again, we all need to be true to our authentic selves. This is true for dating at any age, but I find that as we get older, we not only become more set in our ways, but also more unwilling to compromise on dreams and lifestyle habits. You may be a neat freak that married someone messy and don’t want to sign up for that chaos again. Or, you really want to retire in the country, but your partner is more of a city person. Compromising on your dreams and everyday living preferences can build resentment which can ultimately lead to contempt. It’s hard to imagine that the person who you were so smitten about in the beginning can turn into someone you despise, but it happens all the time. The divorce rate is so high because too many people don’t trust the voice inside them that says something is off. Too many people are afraid to be alone so they accept less than what they deserve and become miserable when things go sideways.

Activity preferences should not be deal-breakers. Yes, it’s great when you and a partner can overlap on several shared interests and enjoy biking or tennis together, but it’s also great to have the things you do just for you or with your friends. Successful relationships require compromise. You don’t need to do or try everything, but if there’s something your partner would really like to experience with you, be open to trying it – at least once. It’s totally natural for men to have more adrenaline pumping activity preferences where women might enjoy more creative pursuits. It’s good to be flexible and accommodating, but to also maintain separate hobbies, your sense of self and independence.  

So, that’s the big picture on dating in your forties with kids. Be patient. Don’t settle. Hold out for a good one. It might feel like trying to find a needle in a haystack, but trust me, you and your kiddos are worth it. And, as my late Great Aunt who never married, but had many suitors used to say, “It’s better to be alone than with bad company.”