I dated my ex after 22 years — I wanted Bennifer, but got heartbreak instead

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There’s only one Bennifer.

After more than two decades apart, Jen Kaarlo, 38, decided to grab dinner with her ex when she was home for the holidays. The romantic rendezvous eventually turned to heartbreak, she said, because she discovered he had found love with another woman.

The pair’s short-lived spark began in 2001, but the high school sweethearts didn’t last after he reportedly enlisted in the Navy.

Despite losing touch, they found themselves in their hometown of Denver for the holidays — and her ex apparently swiped at the opportunity to see his first love again after spotting her Tinder profile.

Kaarlo in high school
Instead of romance, Kaarlo said she was met with rejection — he was seeing someone else.
Jam Press

“I wasn’t sure about replying [at first], and I wondered how he knew I was back, but chalked it up to mutual friends spilling the beans,” the content creator and writer told Jam Press, which did not disclose the man’s name.

“But, in fact, he stumbled across my profile on Tinder and sent a super like, which I didn’t see for a few days.”

She said insistent Facebook messages claiming her ex was “super keen to spend time together” made her rethink her doubts.

“We only had a limited amount of time to spend together before I went back to London for New Year’s — so we saw each other almost every day,” she revealed.

“There was a lot of shared love and a lot of talk about our future, even going as far as to say we would try a long-distance relationship and commit to flying back every few weeks à la Harry and Meghan.”

Kaarlo with her dog
While she was disappointed to hear the news, she said she learned a “lesson.”
Jam Press

That is, until her ex allegedly broke the devastating news that he had his eyes set on another woman — “albeit non-exclusively,” she assured. Instead of rekindling the romance for old time’s sake, she was left pining over her unrequited love.

“It was a rather robust 180 turn from what he was suggesting in the beginning, and I was very surprised, especially as he was the one who initiated all the contact — on a dating app too,” she continued.

While Kaarlo confessed to “doing a little bit of swiping” herself, she reports it was her dad and his partner who urged her to meet up with her ex, despite her father not being a fan of his.

“But he said maybe after all this time, it was possible we were in the right place at the right time,” she said. “I know my dad was disappointed that it didn’t work out and he told me on this trip back home how he pulled my ex aside when I was 17 and told him he wasn’t good enough for me then and would never be good enough for me.”

She added: “My dad suggested that he hoped things had changed, but sadly, things didn’t turn out the way we had both been hoping.”

Jen Kaarlo
The writer and content creator said she’s open to love in the new year after being single in 2022.
Jam Press

This isn’t the first time the two had laid eyes on one another since their love turned sour. Kaarlo claims she and her ex met up in London in 2018 after keeping in touch sporadically.

“He made some references at our last meeting that didn’t seem to suggest he was waiting for me after 22 years,” she recalled. “We’ve got a rather robust history, and I was tentative about opening that can of worms again.”

She claims her ex confessed in 2013 that their split was his “greatest regret,” calling her “the one” — but she was engaged to another man.

Jen Kaarlo
The 38-year-old admitted this wasn’t the first time the pair had met up, either. The two reportedly saw each other years ago in London.
Jam Press

At the time, she was turned off by his “mean-spirited comments” about her line of work, her home and “the life I’ve worked so hard to cultivate.”

“It was strange for him to talk about how he loved me for the last two decades, as it felt more like he was in love with the old me versus looking to connect meaningfully with the person I have become,” she remembered.

This time around, though, she took the rejection in stride, despite having high hopes that the spark might be reignited.

“I’m grateful for the experience and maybe it was just what I needed to launch myself into 2023,” she sniffed before referencing Jennifer Lopez and Ben Affleck marrying last summer after years apart. “While it didn’t end up being my Bennifer moment or the ending of a Hallmark Christmas film, I’m glad I leaned into the experience.”

Jen Kaarlo and man
Kaarlo, left, recalled a time when her ex confessed his regret for their split — while she was engaged to someone else.
Jam Press

After spending last year focusing on herself rather than on men, Kaarlo is ready to ditch her life as a singleton and look for true — and new — love.

“The truth is, I opened up like a flower in the summer sun, and I’m not a cynic after all — I have a whole lot of love to give,” she said. “I think I’m finally ready to give this thing called love a go again, and maybe my high school ex was the one to help me realize it.”

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