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What I’ve Learned From Dating In My 40s


Dating can be better than ever in midlife. One woman recounts the lessons she’s learned so far.

By Theo Pauline Nestor

somehow skipped dating in my teens and twenties. It was the 70s and then it was the 80s. We hung out, more than dated — and then sometimes the hanging out morphed into relationships. But a lot of times, it just morphed into listening to bad Neil Young albums and another round of Coronas. Married at 30 and then
I’ve learned a lot—about myself and about dating in the Middle Ages.
divorced at 42, I arrived at mid-life no more prepared to date than a 14-year-old schoolgirl. But there I was, a schoolgirl with crow’s feet, a mortgage and two kids — heading out into the dating world.

That was six years ago. Since then, I’ve had some disappointments, a lot more fun than I ever expected, a few very late nights, some long talks, a couple of promising relationships and finally a relationship that held more than promise, but through it all, I’ve learned a lot—about myself and about dating in the Middle Ages, or at least, in my middle age. Here’s a little of what I’ve learned.

At Fortysomething, You Have It “Going On” More Than You Think
I wasted a lot of my youth. First, when I was in my early twenties and supposedly at the height of my powers of attraction, I was weighed down by about 20 extra pounds and a rock-bottom self image. Then I lost the weight (but not the low self-esteem) and spent about half a decade embroiled in a tragic, long-distance relationship that always seemed really tempting when we were hundreds of miles apart and then a monstrous mess when we were in the same city for more than 24 hours. Then, after that, I finished out my twenties in a city where 75 percent of the adult males were gay.

By the time I was divorced, youth was over and so I figured were the years — if there ever were any — when men would find me attractive. I was pretty much a stay-at-home mom at the time whose idea of dressing up was maybe a sweat shirt that didn’t have a stain dribbling down the front. But while I’d grown older and my wardrobe had grown shabbier, I’d also sprouted a semblance of self-esteem and confidence and — I’m not saying this to brag, just sharing information with readers who may need it — apparently this shiny self-esteem stuff seemed to count for more than youth ever did because, oddly, men were more interested in me than they had been when I was in my twenties.

The first man to ask me out after my divorce was about seven years younger than me and handsome almost to a fault. We went out once, and while there was frankly nothing between us, the impact on my
Frankly, at this age, it’s not fun just to date endlessly.
sense of self was tremendous. I was stopping in mirrors to give myself a nod. I got a couple of manicures and decided to change my hair and drop the sweats-only wardrobe.

Again, my point here is not to say I’m “all that,” but merely to say that if you are — as I was — someone whose self-image convinces you that you’re invisible on a good day, you might be surprised to learn that the hard-earned qualities you’ve gained over the years just might have made you more attractive. Sure, you may not have morphed into Beyonce, but to at least one crucial group of people you’re suddenly a prospect: those you find attractive and with whom you have something in common.

Adults (Generally Speaking) Are Looking For Adult Relationships
In my twenties, it seemed like relationships were this elusive thing that I was trying to get into and every male I met was trying to evade. Maybe there were lots of guys out there looking for a relationship but I felt drawn to the ones who wanted things to stay “casual” — and after a while, I learned to hide the fact that I wanted to be in a relationship at all. I tried to be cool and casual, but deep down, I was anything but.

One thing I noticed right away about dating in my forties is that the men I met actually wanted to be in relationships. Frankly, at this age, it’s not fun just to date endlessly — you can’t stay up late because you’ll be insanely exhausted the next day, you might have babysitter issues to deal with and most of us are running the engines of our careers and pouring our money into mortgages. Generally, people in their forties want to meet someone so they can stop dating and hunker down on the sofa for the latest episode of Mad Men with someone who’ll pass the popcorn with a kiss. Let’s face it: We — the middle-aged — are often too tired to go out. It doesn’t mean we want to be devoid of love, though.

After 40, You Know Who You Are — So Dating Gets Easier
By this age, you know how you like your steak, how you’re going to vote and whether or not you like opera. Yes, there will still be a few discoveries along the way (otherwise, check your pulse!) but for the most part, you know yourself by now. And the knowledge you’ve gained over the last four decades will help you quickly figure out who could be a match for you and who most definitely will not. Yes, we’re not 25 anymore. But maybe, just maybe, that’s a good thing.


Theo Pauline Nestor is a regular contributor to Happen magazine and author of How to Sleep Alone in a King-Size Bed: A Memoir of Starting Over (Crown 2008).
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