It’s been over a year since I’ve gotten any mail from J. Crew, but I recently received a Spanx catalog.

My favorite band, Matchbox Twenty, released their first album 20 years ago; more than a decade before many of my students were born.

I have 4,875 fewer social media followers than celebrity mini horse Peeps Dolan.

I am the opposite of cool.

Generally, I’m at peace with my uncoolness. My hope is that maybe I give off a “geek chic” vibe—like I’m so content with being uncool that through some phenomenon of reverse psychology I’m actually kind of cool. 

But even the most chic of geeks would feel a little out of place at the Winter Equestrian Festival. So as I planned my month-long stint in Wellington, I vowed to dial down the geek and try to fit in amongst the cool people as much as possible!

I faced my first challenge the night that I arrived in Florida when I had dinner with grand prix sensation Brianne Goutal and hunter phenom Sloane Coles. I know what you’re thinking—those girls are definitely cool and surely they only dine with other cool people.

Well they actually had dinner with me by accident—they visited my home away from home, Eight Oaks South, to have dinner with my stepmom (cool) and my dad (somewhat cool by association) and I happened to be there too. I tried not to be an embarrassment, but then Brianne started to tell a story about her grand prix partner Onira.

“I SAW YOU RIDE HIM ON TV I LOVE HIM!!!” I blurted out. 

I had done really well up to that point.

As it turns out, Brianne and Sloane are both cool and very nice, so they didn’t get up and leave. And when I saw them around the horse show in the following days, they stopped to say hi, even when people were looking. It probably helped that I usually had Holston with me. She’s actually cool.

The next day I took Cowboy out for a hack on the bridle path, because that’s what cool people do. Cowboy looked the part; fat, shiny and decked out in CWD tack from nose to tail.  I hoped that the other riders I encountered would be so distracted by all those dapples and red and white logos that they wouldn’t notice that half of my coolest riding outfit came from Target.

Fortunately, no one we passed seemed too judgmental, in fact, everyone was smiling and friendly. By the time I came up on some riders going a bit slower than me, I was starting to think that I was overcoming my coolness deficit. I slowed to a walk and then pulled up when the two ladies in front of me stopped.  That’s when I spotted the turtles.

I dropped my reins on Cowboy’s neck and pulled out my phone to snap a few pictures of the rare Wellington turtles that actually looked just like the turtles we have in South Carolina. And of course I got busted.

“Does your horse walk faster? Do you want to go ahead of us?” one of the ladies turned around and asked.

You know that video of the kid who randomly confesses “I like turtles,” in a local news interview about a completely different topic? I’m pretty sure that’s what I sounded like when I responded.

“Oh, you go ahead, I’m just taking some pictures of these turtles.” I cringed, but continued, “I’m a tourist.”

“Aren’t we all!!” one of the ladies laughed.

What were the odds that I would run into the only two other regular people in all of Palm Beach County, I thought to myself. What luck!

But as the days passed, I discovered more and more people who, like me, didn’t fit the WEF stereotype. So despite being totally uncool, falling into the lowest income bracket of all WEF attendees, and having almost no chance of winning a ribbon in my VERY competitive professional division, I didn’t feel all that out of place.

Showing Paintball at WEF

By my fourth week in Wellington, I’d long since abandoned all efforts to be anything but myself, as I recounted one of my more memorable WEF moments to my dad:

“Dad, I saw Jimmy Torano today and you won’t believe what he said to me!”

“What?” my Dad responded, genuinely interested.

“He said, ‘Hello Jennifer,’ ” I reported, grinning.

My dad waited. 

Finally, I broke the silence. “That’s all he said. But he knows my name!!”

I am definitely the opposite of cool.

Jennifer Barker St. John grew up as the daughter of two hunter/jumper trainers and rode as a junior and on the Clemson University (S.C.) NCAA team, winning the individual championship in 1998. During her career outside the horse world, she showed her Rhinestone Cowboy to multiple amateur-owner hunter championships. You can read her hilarious introductory blog, “Living The Glamorous Life” to get to know her. 

Now, St. John runs Congaree Show Stables in Eastover, S.C., alongside her friend Elizabeth Grove. They concentrate on students (or as, they call them, “minions”) from 7 to 17 years old who do well on the South Carolina Hunter Jumper Association circuit. “Among our greatest accomplishments: teaching them to wrap correctly and properly muck a stall,” St. John, who serves as the president of the SCHJA, said. She balances training and riding with raising her “sweet, polite, usually well dressed but always sort of dirty” toddler daughter Holston. Read all of Jennifer’s blogs.