dating someone much older


The Dating Scene: When He Tries Too Hard

by Stacey Farrant

It was a warm June evening.  My hair had that tousled look and I was wearing a dress that made me feel very fun and flirty and of course my purple stilettos were to die for.

I was going over to a gentleman friend’s house for a drink. I hadn’t been on the dating scene for long, so everything was an unwritten page to me.

I wasn’t sure if this was just a drink with a friend, or a drink with a possible “more than a friend”. I just knew that I was all dressed up and having a great hair day!

Now, this friend was a few years my senior.  I wouldn’t say that be was old enough to be my father but there was for sure a bit of a generational gap. I was intrigued by his maturity and life experiences and he definitely knew how to treat a lady, just when I thought “chivalry was dead.” Dating an older man was new to me.

Although I enjoyed his company and it was refreshing to have my chair pulled out for me, I was still questioning if the age gap was going to be an issue for me. I was only 38… usually to prep for conversation on a date, I would recap current events, the weather and things that my kids were up to.

I know what you’re thinking – ‘she prepped conversation’.  Well  yes I did!  It had been 22 years since I had been dating.  With this guy, I was already forced to think about Freedom 55 and playing golf in Arizona!

Before the “date”, he told me to show myself in, thinking he would be waiting for me outside on the patio and wouldn’t hear me knock. So as he requested, I just walked in.

To my surprise, he was not on the patio.  Although it was a warm June evening as I had mentioned, I felt heat instantly as I entered the room… and what did I see?  The flames of a roaring fire!

Instantly wondering why anyone would have a roaring fire indoors in June unless you were making Smores, I glimpsed over to lay my eyes upon an older gentleman in his “tighty whities”, perched on the sofa!

This was much like the beloved scene from Seinfeld with George Costanza posing on the velvet loveseat!  Beads of sweat rolled off his forehead as he looked up and said to me in a somewhat sultry voice, “I was warm”.

It took everything out of me not to laugh out loud as I replied:  “Perhaps if you didn’t have a roaring fire in the middle of June, you might have been able to keep your clothes on.”

It was at this point I realized that this was how this guy perceived romance, and what’s worse…what he thought was sexy!!!   Was this a generational thing? Maybe not, but the girls of my era find Mark Wahlberg in a pair of Calvin Klein boxer briefs much more enticing than a pair of Fruit of the Looms!

Needless to say, I was speechless but I stayed and had a very quick and uncomfortable drink. I sat perched on the sofa near the roaring fire that wilted my great hair, until I could use the excuse of picking a kid up from a friend’s house.

As sweet as he was, this just wasn’t where I wanted to be….so until I know for sure that age does make a difference; I will stick to the “GAP” being only a label in my clothes and not a descriptive word between me and guy’s generations!


Stacey Farrant is the single mother of three teenagers, a career woman by day and a self-proclaimed DIVA whenever fighting grime, cooking dinner and running the car pool allows…. all while wearing a 6″ pair of stilettos. Follow her on Twitter.