Why I Decided To Date Twenty-Somethings Again (Or How Porn Turned Millennial Boys Into Men)

After 14 years of monogamy and 10 years of marriage, I found myself a single mother in her late 30s dating in Los Angeles.
Publish date:
November 3, 2015
Dating, twentysomethings, millennials, sex

After 14 years of monogamy and 10 years of marriage, I found myself a single mother in her late 30s dating in Los Angeles.

While well-meaning friends, dating sites and prospective lovers were all quick to ask me what I was looking for, I didn’t really have an answer other than I knew I didn’t want my ex-husband. The rest was an open road.

What I soon discovered is that I didn’t need to know right away, because apparently there is an ocean of possibilities: sex without commitment, commitment with care, a little fun with the possibility of more if it all works out, being the girlfriend to a successful couple who wants another woman in their marriage... You know, the simple things.

Now newly single, I assumed that I would be dating men my own age, but I was informed rather early on by an LA man in his 30s that LA men in their 30s only date women in their 20s, so I dove into that 40-plus dating pool as if I was making up for lost time. I revisited past relationships, met potential dates online, and had the occasional encounter at a bar.

But something seemed wrong and much harder than I remembered. Maybe it was my age? My lack of practice? Or the fact that all these men kept telling me how intimidating I was. How smart. How very clever.

My friend who has dated both men and women bluntly suggested that maybe I should dumb it down. So I tried to take her advice and read all the books I could find about dating.

I stacked up on titles like, “How to Make Him Love You and Never Leave You” and “Be the Bitch, Win the Man.” A proud feminist, I scoffed at some of the antiquated advice like playing dumb as a way to outsmart a man, or books that asked, “Do you want him to know the real you or ask you out again?” I didn’t realize that both wasn’t an option.

And then, one summer afternoon spent at a hotel pool changed the game. He was 25 and a bartender. I was 36 and thirsty.

It didn’t last past a few evenings, but I had discovered something. Suddenly, these younger men were coming out of the woodwork, and not one of them told me I intimidated them in the least.

Here’s what I was looking for! They were intrigued and excited by what I knew and definitely did not carry their baggage around like misanthropic Sherpas climbing up their emotional mountains.

Sure, they have daddy issues and mommy issues just like the rest of us. Career worries and insecurities still abound. Some of them even drank too much, but at least they didn’t seem to be frightened of a strong woman they could talk to over that drink too many.

In fact, they liked it. Millennials grew up with the highest number of working moms in their households to date so it’s no surprise an intelligent and career-driven woman is the norm for them, not an anomaly.

Sexually, it went beyond just the higher libido and increased stamina. I found these young men didn’t need to be taught respect because they already had it.

Growing up in a culture saturated in this more exploratory porn has given these millennial men the understanding that dominance and games of sexual submission are separate from strength and weakness. Because of that, they are also way more likely to understand that no means no.

They do not push or pout, but take it like a man, because quite often the taboos and secrecy of certain sexual behaviors has been taken away.

They seem to understand that there are rules to be discussed and agreed upon and respected, and they have the ability to differentiate sex from life outside of the bedroom. (Or the kitchen floor… or the hallway… or the shower…)

So, yes, I’ll say it – I think porn has helped make all of that possible.

I was elated! I could throw out all of those books! I could enjoy myself! I could listen to another perspective! I could have awesome sex and not feel awkward about it!

My excitement quickly faded as well-meaning (but, let’s be honest, judgmental) friends made me feel like I needed to rein it in.

And after finding out that one too many guy had lied about being older than he was, even I joked that I needed to start carding or I would end up being banned from playgrounds and schools.

All the questions about what I wanted and my own personal insecurities started coming back. I began to wonder if I was just immature and unable to date someone my own age. Was this my female version of the typical male midlife crisis I had always made fun of? I wasn’t entirely sure.

So I decided I would be a grown-up. I would swear off men born after Reagan roamed the White House halls eating jellybeans and reread those dating books I never got around to getting rid of.

I convinced myself I wanted a guy whom I could shop for records with, not one who hears a record for the first time while I make out with him on my couch.

I went back to dating men who were more “age appropriate,” but I found myself once more hearing the echoes of my failed marriage, only now with new people.

All too quickly these well-meaning 40-year-olds jumped to tell me things they thought I needed to hear: how to organize those records they went with me to buy, that I should recycle more, that I should wash my dishes a certain way. Some even liked to pick out the clothes I wore when we went out. (Which was definitely not as sexy as I once imagined it would be.)

They would become insecure and hostile if I knew something they didn’t.

Sexually, it was just as frustrating. They were afraid, cautious even, or they were too extreme.

And despite having come of age in the midst of the Riot Grrrl revolution and the prevalence of date rape awareness in the 90s, these men seemed to have the hardest time taking no for an answer.

Once the clothes came off, they seemed to forget all the rules. A woman who was sexual was now a slut to be treated like meat; or worse, something too precious to touch.

I decided to try the next decade up.

One man in his 50s had fantasies that involved watching his friend have sex with me. I politely declined and ignored the large wad of bills he left next to my purse.

I soldiered on. Another man I dated briefly, who was also in his 50s, wanted me to tell him the story of how I lost my virginity. Retelling the story of my pre-teen deflowering nearly 25 years later to a man for the sake of increasing his passion made me uneasy. I knew then that I would be ending things and he would never meet my daughter.

More than anything, what bothered me was their need to sexually reduce me to merely a physical thing. Though it was “just talk,” I knew deep down that the fantasy of sharing of my body decreased my importance, my strength, and reduced me to a level they could manage.

I knew this because they both told me at one point or another that I am a woman whose brain intimidated them. And there it was again.

I remembered a conversation I had had a few months prior with a friend in his mid-20s. He is handsome, smart, and driven and has dated what he refers to as “considerably older” women.

I was complaining to him how tired I was of being told how intimidating I am. Without blinking an eye, he told me that though, yes, he personally found me a bit “intense” at times, it was, overall, an enjoyable (and not terrifying) quality to be around. It was simple to him and his words encouraged me to be strong and smart and brave and… well… me.

We spend so much time bashing millennials, but maybe they’ve actually got it right when it comes to sex and dating. Maybe it’s us, the Gen-X’ers, who’ve screwed things up so badly.

So I’m taking his advice and I’m going back to the men who seem to have it figured out the most.

And my brain and I have decided that we’re dating men in their twenties… again.