My Experience Dating a (Significantly) Older Man

Originally Published: DECEMBER 7, 2015
Revisited: APRIL 9, 2016

Dating is the most interesting discussion topic during lunch with my girlfriends. Two of us are single, one is happily taken and I’m…in limbo. I’ve deemed myself as the perpetual bachelorette. I go out on dates, and quite a bit of them. But I can’t seem to settle down. That’s not to say that I’m afraid of commitment, but commitment is always the issue on my mind. I don’t like to go past the 2nd date if I know I don’t want to be with the guy long term, or vice versa. That’s just me. I know people who will just go on dates to get “free meals,” but I don’t like that idea at all.

So, when I went on a dating website, right after starting college, my dating game stepped up. I once scheduled a date for every day of the week, it was intense. When I first began actively dating, it was with guys my own age. These dates never seemed to work out, so I aimed higher. While I know age doesn’t necessarily define maturity, I did it anyways. At first, I went for men who were 2, 3 even 5 years older than me. But even then, the age gap was doable. The guys were older, some were mature and getting started with their careers…others, well, they were stuck in the teenage mindset and clearly lacking ambition. Some were just “too busy,” while others weren’t busy enough. But that’s a story for later.

And then, recently, I agreed to go on a date with someone TWICE my age, and on came the arguments and judgement from my acquaintances.

“Ewww! He could be your dad!”

Well, actually, he’s younger than my dad.
And he’s not my dad, so who cares.

“You must like the beer belly look; have fun covering up his gray hair!”

Nope — he looks younger than he is and actually, he’s physically fit and doesn’t have gray hair yet.

“He’s probably cheating on his wife.”

Wrong again. He’s happily divorced, thank you very much.

What I looked at as an innocent coffee date and not a big deal at all, was seen completely differently by those around me. In fact, a guy friend thought it was plain gross. But curiosity got the best of me, so I ignored with everyone’s harsh opinions and went on the date anyway.

Dressed casually, I met him outside of a shopping center. He was wearing a blue button up and khaki pants, nice dress shoes. Quite sexy actually. When he told me his age, I couldn’t believe it. He looked really good. Everything went smoothly; the conversation was filled with stories about high school and witty comebacks. He asked me a lot of questions, something I’m not used to at all, but my sarcastic sense of humor seemed to rub him the right way. Whenever he smiled, his light blue eyes just shined a little brighter. It was all too cute…until we went to order.

He asked for a hot chocolate, the house special. And then it happened. The cashier, in his mid-twenties, asked,

“And what would your daughter like?”

It didn’t faze me, and I simply asked for a hot chocolate as well. It was clear that he was bothered, but we both just brushed it off. We ended up having a really nice time, and he even asked me out on a second date.

But, while it was a great experience, when I returned home I realized that maybe I should take a break from dating in general.
Yes, he was sweet and interesting.
Yes, he was single and not trying to cheat on his wife.
Oh yea, his career is rock solid and he has goals.
His age didn’t bother me, nor did mine bother him.
But he hinted that something was wrong during our talks. He sounded busy, like he was preoccupied trying to find himself. I didn’t want to get caught up in the mix, or ruin his path of self-discovery when I’m still on mine too. Who really knows? Schedules and timing always matters, and at the moment I’m a busy girl, and he’s a busy man.

My takeaway: Dating older men isn’t scary, but make sure you know what you’re getting yourself into.

FASTFORWARD: APRIL 2016

Nothing ever happened past that date. We still chat on Instagram from time to time. Things have gotten stickier from his divorce, but he’s living life. I hope he finds someone who’ll share that passion.
Me? I’m in a “healthy,” lovely relationship…