Summary
- Matt's surprise appearance shakes up Jenn's journey to find love on The Bachelorette.
- A dramatic twist reveals Jenn's history with Matt, adding unexpected depth to the show.
- Bachelor Nation viewers left on edge as Jenn navigates past love and new suitors in Season 21.
Hold onto your roses, The Bachelorette fans, because Season 21 just got a whole lot spicier! Jenn Tran’s latest episode took a jaw-dropping turn when her ex-boyfriend, Matt Rossi, made a surprise appearance to win her back. Talk about a plot twist!

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Jenn Recently Reconnected With Her Ex Before Filming
On Monday, July 29, Jenn, 26, was left stunned when Matt popped up out of nowhere. "For him to come here is just a big shock,” Jenn admitted, still reeling from the surprise.
“We dated three years ago. Matt is not the toxic ex I’m referring to [when I talk about an ex on the show],” she explained. “He’s not the one who messed me up a little bit. We recently reconnected in the past few months as friends — or so I thought as friends.”
Matt, who had been busy in Colombia attending weddings, missed Jenn so much that he jetted off to New Zealand just to see her. After a turbulent on-again, off-again relationship with Jenn that started around 2020, Matt decided to make his move.
During their heart-to-heart, Matt couldn’t resist dropping the L-bomb. “I really do love you,” he confessed, leaving Jenn wide-eyed and speechless with a stunned, “Matthew?!”
With 11 other eager suitors vying for Jenn’s attention, Matt’s dramatic entrance definitely stirred the pot. Despite his best efforts, Matt found himself in the thick of the drama, hoping for a second chance on her journey. And true to Bachelor Nation style, the episode ended with a tantalizing cliffhanger, leaving viewers on the edge of their seats.
Jenn And Matt Began Dating In 2020
Before joining The Bachelorette, Jenn revealed in a December 2023 TikTok that she had a whirlwind romance with a man she called “weiner boy,” thanks to his cute dog.
“Weiner boy and I start going out and I’m completely head over heels in love with him. I wanna marry weiner boy, I wanna be Mrs. Weiner at this point,” Jenn shared. Sadly, the relationship ended three months later, leaving her devastated.
“Which really sucks, because three months later weiner boy dumps me and I’m completely in shambles,” she said. The breakup pushed Jenn to Miami, where she fell in love with the city and applied to PA school.
Matt later confirmed he was “weiner boy” in a February TikTok, humorously narrating their romance with his dog and begging for another chance.
The Bachelorette franchise has been captivating audiences since its debut in 2003. Created as a spin-off of The Bachelor, the show quickly became a staple of reality TV, known for its mix of romance, drama, and unforgettable moments. Over the years, it has provided viewers with a parade of love stories, dramatic breakups, and epic proposals.

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The show’s format involves a single lead — either a bachelor or bachelorette — navigating a pool of potential partners, with eliminations happening each week until the final rose ceremony.
As the drama unfolds, one thing is clear: Jenn Tran’s journey to find love on The Bachelorette is far from ordinary. With Matt’s unexpected reappearance and a dozen new contenders vying for her heart, Jenn's road to romance is anything but predictable. Whether she’ll reconcile with a past flame or find true love with one of her new suitors remains to be seen.
For now, fans will need to stay tuned to see how Jenn navigates this new twist in her quest for love.

The Bachelorette
- Release Date
- January 8, 2003
- Network
- ABC
- Showrunner
- Mike Fleiss
Cast
- Chris Harrison
- Tayshia Adams
- Kaitlyn Bristowe
- Jesse Palmer
- Directors
- Mike Fleiss
- Writers
- Elan Gale
- Franchise(s)
- The Bachelor
- Main Genre
- Reality
- Creator(s)
- Elan Gale
- Seasons
- 21
- Story By
- Elan Gale
- Streaming Service(s)
- Hulu, The Roku Channel
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