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Warning: The Bachelorette Season 21 spoilers ahead. Fans saw him as a dark horse—especially after his viral petting moment—but does Jeremy win The Bachelorette Season 21? His surprising end with Jenn, revealed.
Jeremy Simon, a 29-year-old Real Estate Investor from Fairfield, Connecticut, is one of 25 contestants on The Bachelorette Season 21 with Jenn Tran. Though Jeremy didn’t have as much screen time on The Bachelorette Season 21, at least compared to Jenn’s Bachelorette villains Devin Strader and Sam McKinney—he did have a memorable limo entrance on night one when he drove up to the new Bachelor Mansion in a red sports car and told Jenn: “I know what they say about people who have those types of cars: overcompensating. But, I wanted to let you know that in fact I have a really big… like a really big… [BLEEP].”
Related: All The Bachelorette Season 21 spoilers, including Jenn’s winner
The Bachelorette didn’t confirm the bleeped word Jeremy said, but Jenn did respond, “Did you just say the p-word?” Jenn, for her part, suggested that Jeremy’s limo entrance one of her least favorites in an interview with Us Weekly after The Bachelorette Season 21 premiere. “My not-so-favorite limo entrance was someone telling me that they had a really big penis,” Jenn later told Us Weekly. “I was like, ‘Whoa, too much too soon, buddy.’”
Despite the rough start, Jeremy did make it far on The Bachelorette Season 21, and even had a successful One-on-One Date with Jenn toward the end of the season. But did he win?

Jenn did not pick Jeremy as the winner of The Bachelorette Season 21 and went him home in Week 7 after Hometown Dates, according to Reality Steve. This means that Jeremy came in fourth place.
Jenn’s final three were Devin Strader, a 28-year-old Freight Company Owner from Rosenberg, Texas, Marcus Shoberg, a 31-year-old Army Ranger Veteran from Cloquet, Minnesota, and Jonathon Johnson, a 27-year-old Creative Director from Kansas City, Missouri. Jonathan came in third place; Marcus came in second; and Devin was the winner, according to Reality Steve.
More: Meet The Bachelorette Season 21 cast
Jeremy had one One-on-One Date with Jenn on The Bachelorette Season 21. Their date occurred in Week 6—the week before Jeremy’s elimination—where they went to Pike Place Market in Seattle, Washington, and took part in some fish throwing. Before his elimination, Jeremy—who was one of Jenn’s few finalists who didn’t receive much screen time along with Jonathon—went viral for a clip of him unconsciously patting Jenn’s hair in Week 4.
Jeremy Simon is a 29-year-old Real Estate Investor from Fairfield, Connecticut area, who now lives in New York, New York. His Instagram handle is @j____way. According to his Instagram biography, Jeremy also owns an Airbnb in the Catskill Mountains in New York.
Per his Linkedin, Jeremy works in real estate partnerships with the company Daisy in New York City. He previously worked in real estate acquisitions with the brand AvantStay in Los Angeles, California. Before that, Jeremy worked for companies like JLL, where he was the Director of Capital Markets from 2018 to 2020; Eastern Consolidated, where he was the Associate Director of Investment Sales from 2016 to 2018; and Turner Construction Company, where he was a Project Management Intern from 2014 to 2015.
He graduated from the University of Connecticut with a Bachelor of Science in Engineering, Civil Engineering, and Mathematics in 2016. He’s also a certified personal trainer and nutrition coach with the National Academy of Sports Medicine, and a licensed real estate agent in New York state.
Read Jeremy’s official Bachelorette Season 21 biography and fun facts below:
“Jeremy is a spontaneous, loyal and generous guy who is here to find his forever love. He has had long-term relationships in the past but has been unlucky in love ever since. When Jeremy loves, he loves hard and enjoys coming up with creative ideas for special date nights. When he isn’t working as a real estate investor, he loves staying active, traveling the world, and spending time with his family. He is looking for a lasting relationship where he and his partner can have great communication and share a good sense of humor. Jeremy says his love language is physical touch, and he’s hoping his future wife is ready for all the cuddles and kisses.
Fun Facts:
● Jeremy wants to live abroad someday.
● Jeremy is happiest when he gets a full eight hours of sleep.
● Jeremy’s ideal meet-the-family date would be inviting a girl over for Passover seder.”
The Bachelorette airs on Mondays at 8 p.m. on ABC. Stream it on Hulu.
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