All products and services featured are independently chosen by editors. However, StyleCaster may receive a commission on orders placed through its retail links, and the retailer may receive certain auditable data for accounting purposes.
The devil works hard, but The Bachelor producers work harder. Case in point: Jenn’s ex-boyfriend Matthew Rossi’s surprise appearance on The Bachelorette Season 21 and request to join her season.
Jenn Tran, a 26-year-old Physician Assistant Student from Hillsdale, New Jersey, is the lead of The Bachelorette Season 21. She was previously a contestant on The Bachelor Season 28 with Joey Graziadei, where she was sent home in week six. The preview for The Bachelorette Season 21 ended with a cliffhanger as Jenn was surprised by someone from her past who crashed her season. “What is going on? What is he doing here?” she says in the clip.
More: Meet The Bachelorette Season 21 cast
The preview continued with Jenn telling her cast about her ex-boyfriend’s surprise appearance. “This morning, someone from my past flew all the way here. He wants to be with me, and he wants to join this journey,” she said. While Jenn’s ex-boyfriend’s face wasn’t shown in the preview, Bachelor Nation has discovered who he is and what happened between him and Jenn.
More: All The Bachelorette Season 21 spoilers, including Jenn’s winner
Who’s Jenn’s ex-boyfriend from before The Bachelorette Season 21?
Before she starred on The Bachelor Season 28 and The Bachelorette Season 21, Jenn dated TikTok content creator, Matty Rossi. After The Bachelorette Season 21 trailer showed someone from Jenn’s past surprising her on her season, fans suspected that that person was Rossi based on previous comments he’s made about Jenn’s time on The Bachelor.
Related: Who went home each week on The Bachelorette Season 21
“POV: your ex goes on The Bachelor,” Rossi wrote on a TikTok video of him watching The Bachelor at home. He captioned the video, “Guess she got a type,” along with an Italian flag emoji, a reference to Season 28 Bachelor Joey Graziadei’s Italian background.
In another video, Rossi confirmed that The Bachelor Season 28 contestant he was referring to was, in fact, Jenn. “Alright, the rumors are true. My ex was on The Bachelor. Here’s a little storytime,” Rossi said before having his dog pretend to tell the story of his relationship.
Related: Which Bachelorette couples are still together?
“When I was still a twinkle in my dad’s eyes, he was a 24-year-old fuckboy living in Boston with his three best friends. This really weird thing called COVID had just come to an end…” the dog said. “Anyways, he was painfully single. Not too different than how he is now. So he decided to go on this app called Hinge, which he had never done so before because he was scared of Craigslist killers, and he found this really cute, sweet girl named Jenn. Totally out of his league. Somehow she gave him a chance, they hit it off and they started dating. Things started to heat up and got pretty serious, and Jenn was ready to settle down with her person, but my dad wasn’t there yet. He was still a fuckboy. Anyways, years pass, they stayed friends and now he’s using her for clout.”
Rossi ended the video by joking, “Alright, well there you have it. If you’re not Jenn, you can keep scrolling now. Yo, did you change your number? Why aren’t you answering my texts? Give me another shot.”
Jenn also seemingly confirmed she dated Matty in a 2023 TikTok video in which she explained how her ex-boyfriend helped her get into physician’s assistant school. In the video, Jenn, who refers to her ex-boyfriend as “Wienerboy” (a reference to Matty’s wienerdog), explained that she dated Matty three years prior when she moved to Boston after graduating from college in 2020.
She claimed that she was “completely head over heels in love with him,” however, after three months, Matty broke up with her. Devastated by the breakup, Jenn explained that the split motivated her to leave Boston to attend PA school in Miami, Florida.
Does Jenn’s ex-boyfriend join The Bachelorette Season 21?
Reality Steve confirmed in a blog post in July 2024 that Jenn didn’t allow Matty—who appeared in Auckland, New Zealand, in week four before the fourth Rose Ceremony—to join The Bachelorette Season 21 because she was already four weeks into filming. Jenn clearly doesn’t let him join the show because there’s zero evidence of him anywhere from that moment on. She obviously tells the guys, they’re already 4 episodes deep with her, I assume tell her they don’t want him there, tell him he’s already had his chance with her, and Jenn doesn’t let him continue on the show,” Reality Steve wrote.
Matty also hinted at his negative opinions of Jenn after The Bachelorette Season 21 finished filming in an Instagram Story on the day of her premiere. “can we change the channel?” he captioned a photo of his dog giving him a side eye.
The Bachelorette airs on Mondays at 8 p.m. on ABC. Stream it on Hulu.
