Adventures in dating: Middle age and the madness of matching

Personal stories mostly went by the wayside for me in 2015, when my now ex-husband and I split up. They didn’t go away, but one thing I pledged was to at least seriously limit pieces about my family—unless highly relevant to a particular piece—because my children’s stories were no longer mine to share publicly.

Which is fine, because my primary purpose here and my gift as a blogger, writer, and presenter is to address racism in an accessible way.

When it comes to sharing my personal life, it tends to be tidbits scattered around my social media accounts. I may be a Black anti-racist writer and speaker and executive director of an anti-racism organization, but those things are not the total sum of who I am as a person. I am a mother, grandmother, sister, friend, and woman in the midst of perimenopause, who is navigating life after spending most of my adult life as a married woman.

Some stories need more than the social media treatment, so here we are—at BGIM Media—about to get personal about dating in the mid-40s and beyond.

The last seven years, aside from my work, have been a place of figuring out who the hell I am. Even without a separation and divorce, it would be prime time for midlife re-examina…OK, crisis. Crisis.

While Gen X may be among the coolest bunch of middle-age fogeys to walk this dusty rock, our midlife crises are not the stuff of other historically recent generations. No doubt the fact that we are as almost as broke as our millennial counterparts prevents us from buying extravagantly snazzy new cars or doing some really decadent stuff to announce to the world it’s mid-life crisis time. Instead, we are the sandwich generation, navigating raising and launching kids into the world at the same time our boomer parents are aging or dying and in need of our care—and we realize we are gonna be in deep doo-doo once we reach retirement time. But I digress. 

If you know me personally or follow me on social media, you may be aware that this year has brought an addition to my life. After seven years of navigating the weird and brave new world of life after 20 years of partnership, I met a man! Now that might not seem like a thing to share, much less write about—unless you understand how truly bizarre today’s dating world is. Especially if you are 45 and over and starting over in life.

If you know, you know—sit back and be entertained and maybe learn something new. If you don’t know, strap in for some education.

In the past couple of months, I have received enough messages from fellow middle-aged women—asking my thoughts on dating and meeting people—that I figured a post was in order. Besides, it’s late August, readership drops at this time of year and I am on sabbatical from my day job at Community Change Inc., so I want to keep things light-ish. 

I can say that from 2015 until 2020, while I managed to casually date—and was open to the possibility of a more serious relationship—it wasn’t a necessity or even a deep need. I did at times miss the predictability and even sometimes monotony of partnered life. But I used the first five years after my marriage mostly to grow professionally and figure myself out.

I did have two brief connections during that initial period that straddled the line between relationships and what the younger generations refer to as situationships. One was with a man who, like me, was exiting a 20-year marriage—who after a few months realized that what he really needed was to be alone for a bit to get his head together. The other was with a stereotypical tortured artist type, whose career was tanking along with his mental health, which is why he found himself in Maine living at his mother’s house after years of living abroad. In hindsight, a 40-something-year-old man living at his mama’s house is a huge red flag. However, the New York Times write-ups of his work in the early 2000s helped encourage my common sense to briefly flee the scene. 

It was in 2020 though, after my Dad’s untimely death and the early days of the pandemic, that I found myself yearning for a deeper connection—and a friend’s wedding announcement on New Year’s Eve 2020 gave me the courage to truly try my hand at dating with a goal. My friend, who I will call K, did a Facebook Live as she was preparing for her wedding. She shared how she met her soon-to-be husband.

I should mention that K divorced her first husband around the time I was splitting up with my last husband (yes, I have been married twice, though the first marriage fell apart with breathtaking speed). K shared how 18 months earlier, she sat down and wrote a list of what she wanted in a partner, right down to geographic proximity. K joined a dating app and when she entered her information, only two men met her criteria. Yep, she married one of those two men and, at last check, they are happily living their best lives as two creative types in a blended family. 

I was so inspired by her journey to love that on Jan. 1, 2021, I sat down with my journal and penned my own list of traits I desired in a partner. I signed up for memberships on Match, OKC, Bumble, Hinge, and Tinder. I even paid for memberships, deciding that if I was serious about meeting someone, I needed to expend some resources. 

Less than a week later, I woke up to a beautifully written message from a gorgeous Indigenous man here in Maine. Mind you, on my list, I specifically wanted to meet either a Black man or man of color—I wanted tall, dark and handsome. Along with being spiritually minded, financially stable, etc. I had written this list and at first glance this man met the criteria. We immediately started exchanging messages and a few days later, we spoke on the phone. Our first call lasted over three hours. In today’s world of texting, where no one talks on the phone, this was promising.

After several more lengthy phone calls, we met in person on a brisk Sunday in January. Upon our initial meeting, he seemed to have potential. He was tall, dark, handsome, and also well-spoken and pretty much everything I had put on my list. Except that I felt a gnawing in my stomach, even at that first meeting, though I chalked it up to nerves. 

When your stomach gnaws, you should listen. Barring stomach issues, that is your internal warning system trying to get your attention. But, living in a state where attractive middle-aged men of color are hard to find, I decided not to listen. Which is how over the next several months, I would realize that I was dating an abuser. His abuse was cloaked in an illusion of care, and it took my therapist, brother, and several good friends talking with me—along with me digging into his past—for me to realize that this would not end well. In the first half of 2021, I gained an understanding of gaslighting and narcissism that I could have done without. More importantly, though, I am forever thankful for those in my life who saw what I couldn’t. It took his previous partner four years to get away from him. 

I spent the second half of 2021 unpacking how the hell I could end up in such a relationship and healing myself, while still getting the occasional text from this man. Turns out narcissistic types don’t like when you take your ball and go home. 

Despite the awful dating experience of 2021, I still yearned for a connection and, if we are going to be honest—and since we are all adults here—I also missed physical intimacy. Fast forward to January of this year. I decided to start the great dating adventure all over again, but this time, there would be no list. It would be leaning into my intuition and trusting it as I often have. When I listen, my gut does not lie to me. 

However, unlike previous dating attempts, I decided that this time, my approach was going to be very much like secondhand shopping. Anyone who has ever spent time thrifting knows that the day you go thrifting with a mission is the day you probably are not going to find anything that you want. It is almost guaranteed that if you walk into the local thrift store looking for XYZ, it won’t be there—and if it is, it isn’t available in your style. You might buy something, but when you get it home and cleaned up, odds are high it will sit in your closet until you take your next load to Goodwill. 

The real joy of thrifting is casually browsing with no agenda. That’s the day that you might find vintage Pyrex or Coach purses on the bottom of the shelf for $5. However, those days require that you have no agenda and plenty of patience. That’s why dedicated thrifters visit thrift stores often. 

I reactivated my dating app accounts, but made one minor change. I decided to change my age limits. I have always been a stickler for age, generally gravitating to men a few years older than myself. Why? I had my first kid at 19—my son is now 30. While the phenomenon of younger men with older women has become a real cultural thing—hello cougar life!—I have never wanted any part of it. There are only 19 years between me and my oldest child, so dating someone much younger than me would mean ending up with someone who could be peer-level friends with my son. As a mother, that freaked me out. 

Still, a single girlfriend in her early 50s felt I might have better success if I tried to go younger in age. Which is how, despite my misgivings and ripe age of 49, I decided to widen my search to include men as young as 37. It definitely widened my selection, but I quickly realized that most men that young were not going to be my jam. 

Just when I was starting to feel like a dirty old lady swiping on Tinder, I saw a profile that caught my eye: An attractive man in his late 30s, with a well-written profile and really attractive. According to his profile, our interests seemed aligned and I remember sitting and looking at his profile for a good five minutes before deciding to swipe right. I figured nothing would come of it, but hey, it’s all part of the process! Not like I was going to lose anything if we didn’t match. I would just keep swiping and remember that I was thrifting.

We matched.

And in a rare moment of not my usual thing, I decided I wasn’t going to wait for him to reach out. I was going to reach out. What followed? He responded and his response seemed in line with his profile, and over the course of a few days, we messaged on the app, then moved to texting since dating app messaging is awkward. He suggested we meet for coffee and we did, but he was a few minutes late.

Yes, he called to tell me he was running late, but I have a thing about being punctual. Partially because I live on an island and my life and time revolves around the ferry schedule. See, I had only allotted an hour and a half tops for this meeting. I see the first meeting with anyone from a dating app as a meet-and-greet. It’s not a date. It’s a chance to see if the person is someone you would want to actually go on a date with. It is also a chance to see if there is any chemistry and assess whether or not you could see yourself actually getting naked with this person down the road. 

I have had enough first dates to know that people can take great photos and write witty and charming messages but show up looking like human troll dolls with the personality of a two-day old doughnut. But you won’t know who they are until you meet and, frankly, you want to meet sooner rather than later. While safety is very much a real concern for women, as I know, it’s also easy to fall into the trap of thinking you are getting to know someone via texts and calls. But in some cases, what you are getting to know is their carefully crafted persona and not the real thing. Another hard lesson learned. 

Personally, I don’t need more than an hour to assess if I am vibing with someone. Also, that hour allows me to see if my internal warning signal is trying to tell me something. In this regard, I use the same assessment skills for dating that I have brought to hiring staff. Last year, I hired four people for my day job, all of them through interviews on Zoom. The only one that didn’t work out was the one where I sensed immediately they weren’t a fit—but, for a variety of reasons, I still ended up making an offer. They lasted three weeks. 

Back to my date, though. Our initial meet-and-greet went well enough that he asked if he could walk me to the ferry so we could continue talking. I agreed. The connection was strong enough that it was a no-brainer when we discussed having a second get-together—a proper date—a few days later. 

The second date was amazing. Fast forward six months later, and he recently met my daughter and brother. We also just wrapped up a mini-vacation together. I have to be honest, I did not expect to get to this place—my previous dating experiences since my divorce have generally fizzled out around the three-month mark. My experience being that the new relationship energy starts to settle around three months and you start to see glimpses of who you both really are, and you get a better sense of compatibility—or lack thereof in so many cases. 

Dating in my 40s has definitely been a different experience than dating in my 20s—prior to my divorce, the last time I dated was in 1995. Obviously, we didn’t have the plethora of dating tools that we now have. In some ways that is progress and in some ways, it’s a hindrance to dating. Back before the advent of dating apps and smartphones, dating was primarily a face-to-face endeavor with an investment of time.

Of course, when you are younger it also is a different world. For starters, you actually meet people more organically. Also, when you are younger you tend to be in social circles where a friend may know someone who might be a good match for you. At midlife, it is different. We often don’t have the same organic circles for meeting and, in my case, no one knew any single men in their late 40s and above who would be a good fit. In fact, my observation has been that when a middle-aged man divorces, if he is a halfway decent guy, he is snapped up quicker than a rent controlled apartment in New York City. There is also the reality that divorce in particular can shift your social circles. Suddenly you are persona non grata—no one wants to catch what you have, particularly if you are a woman. You are a member of the formerly married club. 

Another reality at this stage in my life is realizing that I no longer have the expectations around partnership that I had in my 20s. I am not exactly looking for the ring on my finger; I have had two of those. Nor am I looking for kids and the house. I have been there, done that, and could write a book on those things. I am not even sure cohabitation is a goal. But I am looking to share my life with someone—someone to enjoy life with but also someone to share the less-than-stellar moments of life with. 

Over the past few months, as I have shared tidbits about my romantic life, I have heard from women who in some cases want to meet someone but have been hurt a few too many times or who don’t want to deal with the madness of dating.

When I reflect on my own adventures in dating, I will say this: There is going to be some bullshit. It is wishful and unrealistic thinking to not expect some level of bullshit. Case in point: At the same time I matched with my now fella, I also matched with another guy. He was a few years older than me, divorced, and seemed to share some similar interests. I wrongly assumed he might be a good match. 

I actually assumed the younger guy, now my guy, could possibly be a fuckboy. I mean, late 30s, well-spoken and good looking? Yep, something is probably wrong. Actually, a good friend of mine even looked at his profile before we met and said that he looks like a fuckboy. She has now gotten a chance to spend some time with us and admitted that he is a good man. I should add, my brother also has given him the thumbs-up. Meanwhile, the guy from the app who was my age was the guy who ended up sending grossly sexualized messages and dick pics.

Sometimes you play the dating numbers. In other words, don’t get too hung up on any one or two people until you have had a chance to get a sense of what they are really about. Translation: Go out on multiple dates with multiple people. You aren’t committed to any of these people; you are getting to know them. And. just like hiring for a job or looking for a job, more often than not you will interview and be interviewed by multiple companies before you land the job that you want. 

Dating is an adventure very much, like I said before, akin to thrifting. There will be good, bad, and mediocre. The desire for companionship is natural, but as we get older we have had a few too many heartaches and sometimes we stuff that desire down. I say though, if it is something you want, don’t deny yourself. Be willing to take the risk, understanding that ultimately all of life is a risk. Every time you get in your car, you are taking a risk, but you just do it. Even after a fender bender, you get the car fixed and you keep driving. Cars kill more people than bad dates and romantic heartbreak but we still use them. 

As for the apps, in my opinion there is no perfect app for meeting anyone. I have been on them all, and personally, I prefer Tinder. It is quick and to the point, and despite being viewed as the hook-up app, I also have been solicited for sex on the “safer” apps like Bumble and Hinge. While Match is viewed favorably amongst the middle-aged and single crowd, it might be the one site I would pass on. Though, I admit, my most unpleasant experiences have happened with men from Match so I might be unfairly biased against it based on sheer bad luck. 

Look, creepy types are everywhere and by middle age, we have been around long enough to know this. It is just a matter of not taking everything personally or too seriously—including ourselves. I know that is easier said than done, but my experience of dating has been that when I took it too seriously, it was awful. When I accepted that there are creeps and liars everywhere, it became an adventure; a story to share and a laugh to have. 

The meet-and-greets and early stages of dating should be fun. There should be attraction and laughs, while connecting and seeing what you share in common. It is important to know that you share common values—after all, do you really want to eventually find out that the person curling your toes is a Trump cult member? I am going to guess, no. But don’t get hung up on details too much.

As for the checklist, do you really need one? While my friend was able to write a list of what she wanted in a man and it worked out for her, sometimes you don’t need to be that detailed. It’s important to have standards and requirements, but you also might want to be flexible. I won’t lie, I had hoped my next partner would be a man of color. Instead, the universe gave me a tall, dark-haired white guy who spent most of his adult years in the South and who is well-versed in Black American culture. Am I disappointed? Not at all. 

Be open and be honest. After two failed marriages, it would be easy for me to say fuck love and fuck companionship. After all, I have a pretty good life. I have an amazing family, I do meaningful work, and I am at peace with myself and life. I most certainly don’t need a partner. The past seven years have taught me that I can indeed do life on my own with my own terms. But I missed the sharing moments—the intimacy between two people and just knowing that there is one person out there, who when they think of me, they smile and get as happy as I do when I think of them. 

If you want to test the dating waters, do it, and good luck! If you are happily married and over 45, may you never have to learn this brave new world. And if you are happily single, you are a rock star!

Lastly, in today’s world of meeting by apps, if you are over 45 and you do meet someone who you are vibing with, a background check isn’t a bad idea. It definitely adds peace of mind about the person you are spending time with. Yes, I did have a background check run on my guy, and yes, I did tell him afterwards. While many will suggest looking at a potential partner’s social media, that doesn’t doesn’t always tell you everything you need to know, given that not everyone uses social media in the same way.  On that note, happy dating and remember, the dating app is just a human version of the thrift store. You are looking for the treasures that will delight you and those treasures don’t have to make sense to anyone else.

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