Meet Jimmy Leppert - Celebrate Hilton Head's Bachelor of the Year
Author: Jean Wharton
In October of 2006, Celebrate Hilton Head called for submissions for its inaugural Bachelor of the Year contest. Personal questionnaires were reviewed by 20 single women, who ranked each fella’s application separate from his submitted photo. Once the panel of women had narrowed down the applicants to the top 13, they turned them loose to the Hilton Head public. The results are in, and we are proud to introduce Jimmy Leppert as Hilton Head Island’s Bachelor of the Year.
Aside from winning $2000 in cash and prizes, Jimmy was awarded dinner with this blushing writer. By day, he is a mild-mannered Hilton Head Prep English teacher and coach. By night, he’s a dashing bachelor who may be found hanging out at Murphy’s, sipping a Guinness while chatting about poetry and Shakespeare. Intrigued?
The following is a recounting of our mock-date Jimmy was gracious enough to accept so that I could get to know him better and explain to you why he’s the deserving winner of this somewhat superfluous, yet prestigious title.
Jimmy and I sat down for dinner at Antonio’s between his after-school job, coaching HHP’s middle school boys basketball team, and a game with his own men’s club soccer team.
“Intelligent, athletic and handsome… Please explain how you are still living as a bachelor.”
“I was in a relationship up to a few months ago, but once the school year starts I’m fully committed to that. It takes up most of my time. During the school year, I’m immersed in teaching and coaching, which makes it difficult to have a relationship outside of that. In the last year, I’ve started to find a balance between my school work and my life outside of school, and it makes a real difference throughout my life.”
“With your face on the cover of Celebrate Hilton Head, you’re surely going to be meeting some new women. Do you think you’ll be able to make time for the right girl?”
“I hope so, absolutely. I see myself married with a family down the road. Having a family is an ultimate goal of mine. I feel pretty fortunate to have grown up with the family that I have. We’re all very close. I had an exceptional childhood because of my parents.”
“What makes you a good catch?”
“I’m a great dancer.”
“Wow! That’s brave of you to say up front. A good dancer, eh?”
“I’m not afraid to make a fool of myself. I have a very good sense of humor, and I like to have a lot of fun.”
“How did you get to Hilton Head?”
“One of my good buddies from college was from Hilton Head and spoke very highly about this place—so much so that he still had his football jersey from Prep hanging on the wall next to a South Carolina flag. After a learning of a job opportunity with Prep while attending a teacher convention, I was flown down to interview a week later. I was initially interested in teaching abroad in Europe or Indonesia, but my intuition lead me here.”
“How did you feel about being nominated for Bachelor of the Year? What have some of the benefits been so far, aside from having dinner with me?”
“It caught me off guard, so I was a bit hesitant at first; but I took it as a compliment. Since being nominated, I’ve been stopped in the post office and grocery store. I’ve never really been recognized in public, so I’ve enjoyed it while it’s lasted.
“What are you going to do with you Bachelor winnings?”
“First, I’ll pay off my credit card bill. Then I’ll be donating a portion to the Ret Thomas Charity Basketball Tournament at Hilton Head Prep.”
“What was your life like growing up in Virginia?”
“I grew up amongst rolling cornfields on a farm just outside of Richmond. There was a lot of playing outside with my dog and siblings. I went to a boys’ school from kindergarten through senior year—a school much like Prep. Those years really shaped who I am today.
“When did you know that you wanted to go into teaching?”
“I knew in Mr. Burke’s 10th grade English class, reading Alfred Lord Tennyson’s, In Memoriam. Once I heard,‘Tis better to have loved and lost than never to have loved at all,’ that was it. At that point, love didn’t have a great deal of relevance to me in a romantic sense, but I’m a hopeless romantic, and that just clicked with me. I also come from a long line of teachers and people focused on the service industry. My mom was a teacher and an exceptional administrator at the high school level, so she was always a huge inspiration to me.”
“Describe a typical day in the life of Jimmy Leppert, Bachelor of the Year.”
“I get to school early, around 7 a.m. to prepare for the day. Most days, after school, I hold a study group for the middle school that incorporates meditation, writing and yoga. Currently, I’m coaching Prep’s middle school boys basketball team. At night I’m working toward my Master’s degree in Educational Administration through the University of South Carolina. I keep pretty busy.”
“What are you listening to on your iPod?”
“I try to keep contemporary with my students, which means watching MTV and listening to top-40 radio and rap music.”
“What do you do when not teaching, coaching or studying?”
“That takes up most of my time. I hang out at Amigo’s a few nights a week for dinner and keep busy playing in an adult soccer league. On the weekends, I’m still working through a list of about 150 books that I want to read. I started in high school to keep a running tally of books that I really wanted to read, so I’m always working on crossing those off. I literally have a stack of books next to my bed. I also make time to go fishing, and I’ve competed in a few triathlons around the state.
“I’ve found a great community of triathletes, and that’s made it fun. The triathlons in this area are considered “sprint” triathlons, and that’s enough for me at this point. But really, I’ve found a great community on Hilton Head in general from my students, their families and fellow teachers. For example, when I first moved here, a family from Prep, whom I had never met before, hosted a welcome party for me. Another family took me in for three weeks while I looked for a place to live. I immediately felt like a local and part of a larger family. It means a great deal to me, and it helps my parents deal with me being so far from home.”
“You seem like an overachieving, Type A Personality. Would you consider yourself so?”
“Definitely a Type A Personality, but I’ve become much more laid back over they last five years.”
“Would you go back and change anything in your past?”
“My parents gave me the gift of trusting my intuition and following my gut. Even when times have been hard for me, I’ve had to trust myself, and that hasn’t steered me wrong yet.”
“If you could go back and live one year of your life again, which would it be and why?”
I would go back to when I was 19—the end of my fist year in college to the beginning of the second. During that summer, I studied in Valencia, Spain, which was a life-changing time for me. It enriched my appreciation of culture and music. It helped me gain an understanding of our differences as people, but also how similar we are. The fall of my second year of college was the most fun. I have lots of fond memories of that time.”
“You seem to have been inspired at an early to get into teaching. Do you have a mentor who has guided you?”
“Yes. His name is Jay Wood. He is the most outstanding English teacher I had. His dedication to teaching is exemplary. After high school, he spent many days playing lacrosse with me. His unselfish dedication to helping me further my goals in life was amazing. I think of him daily in class, I often ask myself, ‘What would Mr. Wood do?’ I’m still in contact with him for advice in teaching and coaching.”
“Would you recommend participating in the Bachelor contest to any of your friends?”
“Yes. One of my close friends that I teach with at Prep is already campaigning.”
So there you have it—Jimmy Leppert: bachelor, teacher, triathlete, poet and dancer. That’s a lot of titles for a 27-year-old to hold, but he is the embodiment of them all.