Jessop is a recent graduate of Utah Valley University who works at a pizza shop near where he lives in his parents' basement. On "Virgin Diaries," producers film him taking his mother country dancing, hoping her presence as a "wing mom" might help him pick up women. "Any woman that can't get along with my mom is a horrible person," Jessop said.
The show also filmed Jessop on what he referred to as an awkward first date and in his "40th makeout session." The hour-long show also will feature a 29-year-old lesbian virgin trying to find love, despite her obsession with "Star Wars" and dodgeball. And there will be an update on Ryan and Shanna, a couple who had their first kiss on camera in a previous episode.
In his quest to find his perfect mate, Jessop said he has been out on at least 500 first dates, something he sees as an accomplishment, not something to be embarrassed about. He finds dates in numerous places: his Mormon singles ward, country dancing, speed dating and even "trolling" on Facebook.
He thinks of dating in mathematical terms and asks out as many women as possible. "If you ask 10 women for their number, maybe one will go on a date with you," he said.
Jessop has another dating strategy that some might find questionable: bribery. Women who go out with him receive a custom-made Skippy T-shirt, that proclaims "Skippy is my friend." He has a second shirt for girls who will make out with him for at least three minutes.
Out of all his dates, he became serious with three women, but none of those relationships lasted longer than one month.
Staying a virgin for 34 years hasn't been easy, Jessop said, but he is committed to the standards of being a temple-worthy member of The Church of Jesus Christ of Latter-day Saints. "It's the temple or bust for me," he proclaimed.
Jessop admits he's nervous about all the personal information that will be shared with viewers, yet he's confident about himself and his choices. "If I am worried about them filming me being odd, then I shouldn't be odd to begin with," he said.
The "Virgin Diaries" episode isn't Jessop's first time in front of the camera. Two years ago, he was the subject of "Sundance Skippy," a documentary produced by Mark Hendengren that was screened at the LDS Film Festival in 2012.
The documentary explored the unique ways Jessop tried to get pictures with celebrities during the annual Park City film festival. During filming, the producer and subject became friends, and Hendengren came to appreciate how complicated Jessop was as a person.
"He is really conflicted," Hedengren said. "He really likes girls but he also wants to be a good Mormon. Those are his two biggest motivators in life."
'The Virgin Diaries'
The TLC special airs Wednesday, July 18 at 8 p.m.