The Bachelorette season 21 lead Jen Tran was in for an unexpected surprise when the ex-boyfriend Matt Rossi appeared to win him back.
“For him to come here was just a shock,” Jenn, 26, said on the Monday, July 29, episode of The Bachelorette. “We dated for three years. Matt’s not the toxic ex that I thought he was (when I talked about exes on the show). He’s not the one that makes me a bit confused. We just reconnected in the last few months as friends – or what I thought were friends.
Matt explained that he was in Colombia for two weddings, but missed Jenn so he flew to see her in New Zealand. Jenn, who dated Matt after their initial relationship around 2020, began challenging him.
“You can say this before I go,” she said, and he replied, “I did say it, but I didn’t say it as well as I thought.”
During the conversation, Matt drops the L word. “I really love you,” he says, while Jenn exclaims, “Matthew?!”
While Jenn now has 11 other suitors vying for her affection, Matt shared that he’s happy to be a part of her journey on the show.
After Jenn walks away from the interaction, the episode — true to Bachelor Nation fashion — ends on a cliffhanger.
While Matt isn’t Jenn’s most toxic ex, he does have a history of ups and downs. A month before he started filming The BacheloretteJenn took to TikTok to explain that she started dating a man – whom she refers to as “weiner boy” because of his dog – after moving to Boston.
“Weiner boy and I started going out and I really love him. I want to marry Weiner boy, I want to be Mrs. Weiner this time,” Jenn recalled in a December 2023 video. “That really sucks, because three months later Weiner boy dumps me and I’m completely shambles. I don’t know what to do. This is the first real relationship I’ve been in since college.
Jenn explained that the breakup led her to travel to Miami, and that she fell in love with the city. She then applied to PA school in Miami, which was the only school she got into.
“If weiner boy wasn’t born and didn’t break my heart, I wouldn’t be fulfilling my dream right now,” Jenn said.
Two months after Jenn uploaded the video, Matt confirmed his identity as “weiner boy” on his own TikTok. In a video uploaded in February, Matt enlists the help of a weiner dog to tell the story of how he met Jenn on Hinge.
“He found this cute, sweet girl named Jenn, out of his league,” Matt said from the dog’s point of view. “Anyway he gave her a chance, she stopped and started dating. Things started to get serious and Jenn was ready to settle down but my dad wasn’t there yet.
Matt called him a “f–k boy”, noting that the pair remained friends and were now “using him for leverage” in the midst of his work. Joey Graziadei’s season 28 of Scholar.
“Help me again,” Matt says at the end of the video.
The Bachelorette airs on ABC at 8 pm ET.