Online Dating in My 40s Was Hell. One Intense Moment Changed Everything

When I first joined an online dating app after separating from my husband, I thought it would be a joke. I was an overweight mom of two children, one of whom has special needs, with no great wealth or high income. I never expected to meet the love of my life.

At first it was a slew of unsolicited d*** pics, and a quick lesson in how very different online dating was from how I'd met my husband in the smoking section of a Denny's after clubbing 20 years earlier.

I was 39 years old when we initially separated, and there were two messy years before the divorce was finalized. It took going to therapy, life coaching, and fitness coaching for a year, to completely change my outlook on what a relationship means, and to find my self-esteem again.

Jennifer Simas
Jennifer Simas is an intimacy coach at The Intimacy Ally. She is pictured with fiancé Zach. Jennifer Simas

It wasn't until December 2021 that I had the courage to sign up for online dating. By this stage I was 41 years old, and had set my age requirements from 20 years old up to 50 years old, just to see what sort of person popped up.

I received many responses from really young guys who were just looking to hook up with somebody who was older. I had never experienced anything like this before, but believe it may have something to do with my age, or the fact that I was considered not as attractive as other users.

I feel certain guys on these apps prey on women who might not have the self-confidence to say no; who think "this is the only option I have, because I'm 45 and I don't know what else is going to happen."

So I adjusted my age range to 25 years old and over, in the hope of knocking some of that out, and I did. But even many of the older guys were disrespectful. They would have minimal exchanges with you before asking for nude photographs.

It seems like everybody has become so bold and so brazen behind these screens; I'm sure many of them wouldn't behave the same way if they met someone in person, and I feel we need to be teaching this younger generation of men a better way to behave online.

I was on the app for around two months, and was on the verge of canceling my subscription when I received a like and a message from this Viking-looking guy who was 16 years younger than me.

I had swiped past him a couple of times—his main picture was of him hiking, and I hate hiking—but we exchanged numbers and started talking one day while he was at work repairing engines on tractor-trailers.

We had our first date at my house and initially I was just looking for fun. He ended up staying over, and at 3 a.m. my daughter started banging on my door saying her brother had thrown up.

"Stay here, and don't leave without putting on a shirt," I told him.

This is too much for him, he's 25 years old, I thought as I got my son cleaned up, started his laundry, and went down to the living room with both kids.

When I heard stirring upstairs around 7 a.m. I swore he'd run out so fast my head would spin. But nope. There he was, standing on the stairs asking if there was coffee. I made some, and he hung out watching TV with us for another two hours.

When I walked him out I told him I couldn't believe he stayed.

"You did tell me you were a mom, remember? Kids get sick. And your kids come first. I like that about you."

I wouldn't admit that I loved him for a few months, but I knew right then. He was it.

Jennifer Simas
Jennifer and Zach plan to marry next year. Jennifer Simas

Our third date was at my house. I made dinner and introduced him to my good friends, who brought their kids over. All night I was managing the playlist and he asked several times if he could play me this one song.

The night ended, my kids were up in bed and my neighbors had all gone home. We had cleaned up the kitchen, and he said: "Okay, can I play you this song now? It really makes me think of you."

I said okay and this country song started playing. There he was, standing in the doorway between my kitchen and dining room. I wrapped my arms around him, looked up at him and said: "Ya know, we're in a great position to start dancing."

"Oh yeah? I wouldn't know," he said.

"You've never danced with a girl before?"

"No. We were poor. I didn't go to dances," he replied.

"Well, we're in a good position. Keep your hands on my hips, I'll keep wrapped around your neck. Now, just move your feet to go in a circle."

So, he did, and we danced as Cover Me Up by Jason Isbell played. On the second verse, he started singing along and looking at me with his bright blue eyes and I swear, I thought I was in a Hallmark movie.

As he sang the lyrics: So cover me up and know you're enough to use me for good, I said: "Is that what you want Zachary? You want me to use you for good?"

"I do," he said.

Well, it's been a done deal ever since. That was the moment. That was when my heart softened and that angsty bitter lady who thought she would never marry again could totally see it as a possibility with this guy. Four months later we moved in together.

Six months after the move, we went for a hike near Washington, D.C. I'm not so great at hiking, but he had done the trail before and told me I would be okay because there was a lot of flat land.

But when we got there, we accidentally went down the billy goat trail—meaning we were climbing and sliding down 4ft high rocks all over the place. He's six foot and I'm four foot ten. I was ready to kill him.

After a while, we sat down for a minute and he said: "Do you want to murder me, actively right now?"

"No, not right now," I replied.

"Okay. Cool," he said, before pulling out a ring.

Now, we're planning to get married in the summer next year, and I've never felt this way before.

I struggle to explain what it's like to have been through 25 years of dating, always getting it wrong, to then finding the love of my life. My partner is the most excellent stepdad and the most gentle giant.

I waited 20 years to get myself into a healthy, supportive, and loving relationship. And I want other women to know that it's possible.

The biggest hurdle was not understanding that I had to love myself and say: "This is what I am. These are the things that I can try to adjust to, and these are the things that I can't."

I learned that if someone doesn't agree with that, or wants to change me in any way, then I don't need anything to do with them.

Jeni Simas is an intimacy coach at The Intimacy Ally.

All views expressed in this article are the author's own.

As told to Newsweek's My Turn associate editor, Monica Greep.

Do you have a unique experience or personal story to share? Email the My Turn team at myturn@newsweek.com.

Editor's Picks

Newsweek cover
  • Newsweek magazine delivered to your door
  • Unlimited access to Newsweek.com
  • Ad free Newsweek.com experience
  • iOS and Android app access
  • All newsletters + podcasts
Newsweek cover
  • Unlimited access to Newsweek.com
  • Ad free Newsweek.com experience
  • iOS and Android app access
  • All newsletters + podcasts