‘The Bachelorette’: Get to Know Jenn Tran’s Ex-Boyfriend & Their Complicated History

Avery Thompson August 5, 2024, 2:06 pm

Jenn Tran got a blast from the past during her journey to find love on The Bachelorette. In the July 29 episode of the ABC dating show, Jenn was shocked when her ex-boyfriend, Matt Rossi, showed up out of the blue and wanted her back.

Matt told Jenn he wanted to join the show, but Jenn didn’t make her decision by the end of the episode. Matt joining the suitors would turn the entire season upside down. So, who is Jenn’s ex-boyfriend? What’s their history? Let’s break down what we know about their relationship and what’s next.

Who is Jenn Tran’s ex-boyfriend?

Obviously, Bachelor Nation fans know that Jenn dated Joey Graziadei during The Bachelor Season 28. Before Joey, Jenn dated digital creator Matt Rossi. The 27-year-old is an insurance executive from Atlanta. He’s also known for his Instagram and TikTok content with his wiener dog, Kirkland.

In February 2024, Matt posted his own video and confirmed he was the “Wiener Boy” Jenn referred to in a previous video. He revealed that he met Jenn on Hinge and called her a “really cute, sweet girl” who was “totally out of his league.”

Their relationship got “pretty serious,” but Matt said he was a “f**kboy” and fumbled his chance with Jenn. However, they remained friends after their breakup.

Is Jenn’s ex-boyfriend going to join The Bachelorette?

In the trailer for Jenn’s season of The Bachelorette, her ex-boyfriend’s surprise appearance was teased. Jenn was thrown off guard when someone from her past showed up. “What is going on? What is he doing here?” she said in the footage.

Jenn Tran’s ex-boyfriend Matt Rossi (Instagram)

“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 later told her suitors. Her ex-boyfriend’s face was not shown in the trailer, which added to the mystery and drama.

In the July 29 episode, Matt showed up in New Zealand. Host Jesse Palmer revealed that Matt reached out to a producer and flew to New Zealand on his own dime to talk to Jenn. “I’m here to tell Jenn, ‘I still love you and that I’m here to show you that and whatever I have to do to earn that trust back. I’m here to see if there’s a future with us.'”

Matt walked out to where Jenn was filming to speak with her. They were supposed to go to Colombia together for weddings, but he went without her as she filmed The Bachelorette. Matt decided to fly from Cartagena to New Zealand to be with Jenn.

“We were in love, and I think a part of us will always be in love,” Matt said in his confessional. “For me, it’s just never been so strong. Me being here, hopefully, is one step in the right direction to proving to her how much she means to me and how seriously I’m taking this.”

Matt told Jenn, “I’m not ready to just let you go and get engaged without telling you that I still have really strong feelings for you, more now than ever. I’m just asking that you give me the chance to show you how much this all means to me.”

When Jenn asked Matt if he was ready to get engaged, he replied, “I’m ready to do it.” Jenn admitted she was confused and blindsided by Matt’s unexpected appearance. “You know you could have said this before I left,” she told him.

Matt stressed to Jenn that he wanted to fight for their relationship—even if it meant joining the show. “I would love to join you for me to prove to you how much you mean to me, to express to you how much I still strongly care for you.”

At the end of the July 29 episode, Jenn hadn’t decided whether Matt would join the suitors. However, we did see a preview of him dressed up for the rose ceremony.

Ahead of the August 5 episode, Matt shared an Instagram video of himself getting ready for the rose ceremony. “SEE YALL TONIGHT,” he captioned the video.

When did Jenn and her ex-boyfriend date?

In a 2023 TikTok video, Jenn explained her relationship with Matt, whom she referred to as “Wiener Boy” because he posts about his wiener dog on social media.

One Suitor Leaves Suddenly & 2 More Are Eliminated on 'The Bachelorette'

She started dating Matt three years ago when she moved to Boston right out of college in 2020. Jenn said she was “completely head over heels in love with him.”

However, after just three months, Jenn’s ex dumped her. She was devastated by the breakup, but the sudden split pushed her to attend physician’s assistant school in Miami.

When Matt showed up in New Zealand, Jenn revealed that they’d recently “reconnected” as friends after their breakup.

The Bachelorette, Season 21, Mondays, 8/7c, ABC