The Bachelorette season 21 lead Jenn Tran was in for an unexpected surprise when her ex-boyfriend Matt Rossi showed up to win her back.
“For him to come here is just a big shock,” Jenn, 26, said during the Monday, July 29, episode of The Bachelorette. “We dated three years ago. Matt is not the toxic ex I’m referring to [when I talk about an ex on the show]. 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 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 on and off after their initial relationship around 2020, began challenging him.
“You could’ve said this before I left,” she said, to which he replied, “I did say it but I didn’t say it as grandly as this I guess.”
While conversing, Matt dropped the L-word. “I really do love you,” he said, as Jenn exclaimed, “Matthew?!”
While Jenn now has 11 other suitors vying for her affection, Matt shared that he’d love to be part of her journey on the show.
After Jenn walked away from the interaction, the episode — true to Bachelor Nation fashion — ended on the cliffhanger.
While Matt isn’t Jenn’s most toxic ex, they do have a history of ups and downs. Months before she began filming The Bachelorette, Jenn took to TikTok to explain that she began dating a man — whom she refers to as “weiner boy” because of his dog — after moving to Boston.
“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 recalled in the December 2023 video. “Which really sucks, because three months later weiner boy dumps me and I’m completely in shambles. I don’t know what I’m going to do. This is the first real relationship that I’ve ever had out of college.”
Jenn explained that the breakup prompted her to take an impromptu trip to Miami, and she fell in love with the city. She subsequently applied to PA school in Miami, which ended up being the only school she got into.
“If weiner boy wasn’t born and didn’t break my heart, I would not be fulfilling my dreams right now,” Jenn said.
Two months after Jenn uploaded the video, Matt confirmed his identity as “weiner boy” in a TikTok of his own. In the video uploaded in February, Matt enlisted the help of his weiner dog to tell the story of how he met Jenn on Hinge.
@themattyrossi Replying to @hulu Kirkland tells all #thebachelor #wienerboy #storytime
“He found this really cute, sweet girl named Jenn, totally out of his league,” Matt explained from the perspective of his pooch. “Somehow she gave him a chance, they hit it off and they started dating. Things started getting pretty serious and Jenn was ready to settle down but my dad just wasn’t there yet.”
Matt called himself a “f–k boy,” noting that the pair have remained pals and he’s now “using her for clout” amid her stint on Joey Graziadei’s season 28 of The Bachelor.
“Give me another shot,” Matt said at the end of the video.
