Plot Twist! Jenn Tran's Ex-Boyfriend Crashes the Party on 'The Bachelorette'

Jenn Tran dated her ex-boyfriend, Matt Rossi, for three months.

Allison DeGrushe - Author
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Updated Aug. 6 2024, 7:38 a.m. ET

Jenn Tran's ex-boyfriend, Matt Rossi, shows up on Season 21 of 'The Bachelorette.'
Source: ABC

Spoiler alert: This article contains spoilers for Season 21, Episode 5 of The Bachelorette.

We're five weeks into Jenn Tran's season of The Bachelorette, and the drama just keeps escalating! In Episode 4, things take an unexpected turn when someone from our leading lady's past shows up to meet with her in Auckland, New Zealand.

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Toward the end of the episode, host Jesse Palmer drops a bombshell: Jenn's ex, Matt Rossi, has arrived and wants to have a word with her. When Matt finally meets Jenn, he confesses that he's still in love with her and wants to join the show.

Jenn is clearly torn, leaving us all wondering: Does her ex-boyfriend end up joining her Bachelorette journey? Jenn makes up her mind in Episode 5.

Matt speaks with Jenn during Season 21 of 'The Bachelorette.'
Source: ABC
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Does Jenn Tran's ex-boyfriend join 'The Bachelorette'?

Much to the relief of Jenn's guys, Jenn's ex-boyfriend Matt does not join Season 21 of The Bachelorette. Even though Matt arrives to ask to be part of Jenn's journey, she knows he's part of her past. But to amp up the drama, Matt has to go inside and talk to the guys about it before he leaves for that long flight home.

Although Jenn's guys are relieved that Matt doesn't join The Bachelorette and that Jenn's ex is still her ex, they aren't happy to see his face. He apologizes for coming and for potentially messing things up for anyone. And, just as fast as the bombshell of Jenn's ex's arrival dropped, it's over.

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Jenn Tran and her ex-boyfriend, Matt Rossi.
Source: ABC

Jenn Tran and her ex-boyfriend, Matt Rossi.

And honestly, it was clear that Jenn wasn't keen on letting Matt join her season. When he shows up Jenn is absolutely stunned, calling his appearance a "big shock." And when he starts with his extravagant romantic gesture, things only seem to spiral further downhill.

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Matt tells the physician assistant student that he still loves her and begs for a chance to prove how much she means to him. He even goes as far as to say that he's ready to get engaged and be with Jenn for the rest of his life!

Jenn is clearly baffled and tells Matt that his sudden declarations are coming out of left field. The leading lady points out that he could have shared all of this before she left for filming, especially since they had recently reconnected as friends — at least, that's what she thought.

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Jenn revealed that Matt broke her heart "so badly."

When Jenn moved to Boston right after college, she started dating Matt, whom she calls "Wiener Boy" because of his beloved wiener dog that he posts about on social media.

Jenn quickly fell head over heels for Matt and even envisioned marrying him. But just three months later, Matt ended things, leaving Jenn feeling utterly devastated.

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"At this point in my life, I think Wiener Boy dumping me is rock bottom. Like, I have never experienced a lower low," she recalled via TikTok. "I didn't eat for a week, I didn't sleep ... I couldn't do anything. I just remember feeling, like, I lost everything."

Jenn Tran speaking with her ex-boyfriend, Matt Rossi, on Season 21 of 'The Bachelorette.'
Source: ABC
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Despite the heartbreak, Jenn revealed that Matt's breakup actually inspired her to apply to graduate schools outside of Boston. After a girls' trip to Miami, Jenn fell completely in love with the city and decided to apply to physician assistant programs there.

"I probably applied to 10 schools at this time, I think, and every single one of those schools rejected me — except for the school in Miami," she shared. "So if I never dated Wiener Boy in the first place and Wiener Boy never broke my heart so badly... I would've never gone to Miami and I would've never applied to a school in Miami."

Jenn continued, "If I never applied to Miami, I never would've gotten into PA school and I wouldn't be in PA school right now, which is crazy! If Wiener Boy hadn't broken my heart, I wouldn't be fulfilling my dreams right now."

The Bachelorette airs on Mondays at 8 p.m. EST on ABC. Stream the next day on Hulu.

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