Jenn Tran has revealed why she and ex-boyfriend Matt Rossi, who just showed up asking for a second chance on The Bachelorette, initially broke up.

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On The Bachelorette's July 29 episode, Matt -- who had traveled all the way to New Zealand on his own dime, according to host Jesse Palmer -- surprised Jenn in Auckland right before the fourth Rose Ceremony of Season 21 was about to commence.

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Matt, a 28-year-old Boston-based beer salesman and content creator, told the cameras he and Jenn had dated for several months "about three years ago," when Jenn had been living in Boston prior to her move to Miami, FL, for PA school.

Jenn then shared while filming The Bachelorette in April that she and Matt -- who was admittedly "a f-ckboy" at the time he had dated Jenn -- had "recently reconnected in the past few months as friends."

When asked to share details about their short-lived romance, Jenn shared on the "Bachelor Happy Hour" podcast, "We met on Hinge and we dated for three months-ish... We were [exclusively] boyfriend and girlfriend."

Jenn told co-hosts Joe Amabile and Serena Pitt during the podcast's Thursday, August 1 episode that "things just didn't really work out."

Jenn, now 26, explained how they were both "really young" when they were together, which is a "classic" reason for breakups.

"We were just so young, and so he never prioritized me and I was still learning so much about myself. I didn't know how to communicate, and I didn't know how to be in a good relationship," Jenn confessed.

"I was just kind of a mess too, and so, it just didn't work out."

Serena said it sounded like Jenn and Matt didn't have the skill set to nourish a healthy relationship at that time in their lives and so it just "fizzled out," and Jenn agreed.

Jenn confirmed on The Bachelorette's latest episode that Matt was not the "toxic" ex-boyfriend who had "messed [her] up a little bit" in the past.

"I think a few months passed [after our split] and then we got back together for a little bit, and then I decided, 'This is just not it.' And then a few more months passed after that [and we had] a second reincarnation," Jenn revealed on the "Bachelor Happy Hour" podcast.

"I was so happy with that because he is someone who is such a good person, and I kind of came to terms with the fact that we're at different places in our lives. So we had stayed in touch as friends for, like, a couple years."

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Jenn shared how she and Matt spoke "here or there" and their connection was "nothing crazy" at that point.

After filming Joey Graziadei's The Bachelor season, Jenn recalled speaking to Matt on the phone "every now and then" about TikTok videos and other stuff.

"He was somebody I could talk to about stuff on TikTok and whatever else was going on in my life," Jenn explained.

"I've known him for so long and he knows my family and I know his family, and so we have this history and I found comfort in that. So I was surprised when he came and basically confessed his love!... We were in New Zealand!"

While Jenn had clearly friend-zoned Matt, he said he was in love with her and finally felt "ready" to get engaged.

Matt shared with The Bachelorette star how he had ditched two weddings in Colombia to fly to New Zealand in order to fight for Jenn and show her how much she meant to him.

Jenn confirmed that she was supposed to go to those weddings with Matt as his friendly plus one.

"There was a free trip to Colombia on the table at some point, and I had said, 'Matt is a really good friend of mine, he needs a little date, he wants to give me a free trip to Colombia -- why not?!'" Jenn admitted.

Although Jenn and Matt were pretty close and had established mutual trust, Jenn naturally questioned his intentions for going on The Bachelorette because she said he had "so many chances" to be with her before her televised journey to find love.

Matt told Jenn on The Bachelorette, "I feel like we've been able to connect on a deeper level. You are one of the most important people in my life, and you know me better than anyone else in the world. I'm not ready to let it all go."

"You know you could've said this before I left," Jenn replied.

"I did say it," Matt responded. "But I didn't say it as grandly as this, I guess... I really do love you."

The Bachelorette episode ended on a cliffhanger, with Jenn contemplating whether to allow Matt to join her cast of bachelors and compete to win her heart.

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A preview for what's to come on The Bachelorette suggests Jenn decided to welcome Matt into the competition. Click here to read The Bachelorette spoilers to find out if that was really the case, and also for details on the ending of Jenn's season.

Click here to read episode-by-episode spoilers about how Jenn's The Bachelorette season unfolds, including who Jenn picks as her winner and runner-up.

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About The Author: Elizabeth Kwiatkowski

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