Why Did Jenn & Matthew Break Up Before The Bachelorette? The Real Reason For Their Split

Warning: The Bachelorette Season 21 spoilers ahead. Bachelor Nation fans know to never trust an ex, so when Jenn’s ex-boyfriend , Matthew Rossi, surprised her mid-season in New Zealand, viewers’ red flags were immediately up and wondering the real reason Jenn and Matthew broke up before The Bachelorette Season 21 premiered.

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Jenn Tran , a 26-year-old Physician’s Assistant Student from Hillsdale, New Jersey, is the lead of The Bachelorette Season 21 . She was originally a contestant on The Bachelor Season 28 with Joey Graziadei , where she was sent home in Week 7. However, Joey isn’t Jenn’s only notable ex. In Week 5 of The Bachelorette Season 21, Jenn’s ex-boyfriend from three years ago, Matthew “Matty” Rossi, surprised her in New Zealand to profess his love for her and to ask to join her season.

The episode ended on a cliffhanger as to whether Jenn allowed Matthew to be a part of the Season 21 cast, however, Reality Steve confirmed that Matthew did not join Jenn’s season. Still, fans wonder exactly what happened between Jenn and Matthew before she became the Season 21 Bachelorette and what their relationship was like prior to her becoming Bachelor Nation’s newest lead.

Why did Jenn and Matthew break up before The Bachelorette Season 21?

Matthew, who has more than 50,000 TikTok followers under handle @ themattyrossi , revealed in a video in February 2024 that he broke up with Jenn because she was “ready to settle down” while he was still in his “fuckboy” era. The video was told through the perspective of Matthew’s wienerdog.

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“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.”

He continued, “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.”

Matthew 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.”

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During an interview on “The Viall Files” podcast in August 2024, Jenn confirmed that she dated Matthew three years prior to The Bachelorette Season 21 and that he was the one who broke up with her. She explained that, after their breakup, they remained friendly and got dinner here and there when Jenn would visit Boston, where she and Matthew first dated and where her family still lives.

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Though they kept in communication, Jenn, who lives in Miami for physician’s assistant school, told “The Viall Files” that “there was nothing there” romantically because they lived so far away from each other.

Jenn also denied that she and Matthew were ever “in love,” like he claimed on The Bachelorette Season 21. “We were in love — and I think a part of us will always be in love,” Matthew said in the episode.

In response, Jenn told “The Viall Files,” “We were never in love.” She also confirmed that she and Matthew only dated for three months. When asked whether she thought Matthew appearing on The Bachelorette was a ploy to boost his TikTok following, Jenn told the podcast that the thought “definitely” crossed her mind.

Jenn’s claim that she and Matthew were never “in love” is a stark contrast to a TikTok video she shared in 2023 about how her relationship with an ex-boyfriend—who she referre to as “Wienerboy,” a reference to Matthew’s wienerdog—inspired her to enroll in physician’s assistant school.

In the video, she claimed that she was “completely head over heels in love with him, however, after three months, Matthew broke up with her. The breakup motivated her to leave Boston for Miami to study to become a physician’s assistant.

Jenn also confirmed on “The Viall Files” that Matthew wasn’t the “toxic” ex-boyfriend that talked about during The Bachelorette Season 21. She explained that she dated that ex two years ago for a year and that the reason for their breakup was because he still hadn’t introduced his mother to her a year into their relationsip.

The Bachelorette airs on Mondays at 8 p.m. on ABC. Stream it on Hulu .

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