Kelley Flanagan Details Cheating Scandal with Ex-Boyfriend

The Bachelor alum Kelley Flanagan is newly single after her break-up with Ari Raptis, claiming that they split over infidelity issues and his subsequent lies.

“For the past year and a half, I was in a relationship and, I mean, big things were moving,” Flanagan, 32, said on the Wednesday, November 27, episode of the “Chicks in the Office” podcast without ever mentioning Raptis by name. “I moved to Philadelphia; I moved in with this guy … and we had amazing times.”

She added, “At this point, it’s hard for me to even remember those good times, which is kind of sad but it’s my truth. I’m like, ‘What the hell was real and what wasn’t?’”

Flanagan — who appeared on Peter Weber’s season of The Bachelor and dated the lead on and off for more than a year after the 2020 season — debuted her relationship with Raptis in June 2023, recalling on Wednesday that “things moved fast.” She confirmed their breakup earlier this month, noting via TikTok that her “heart is shattered” after an apparent betrayal. (Raptis has not publicly addressed the split. Us Weekly reached out for comment.)

While Flanagan never sold her apartment in Miami as a “safety net,” she relocated to Raptis’ home base in Philadelphia to “be on this guy’s page.”

“I was always on his terms and I, like, stopped doing so much of my work. I stopped doing so much influencing,” she recalled on the podcast. “I stopped seeing my friends as much, and … I just felt I was losing [myself]. I had a really tough time, so I vocalized that and we ended up breaking up in April.”

According to Flanagan, she opted against sharing the split news on social media at Raptis’ request. Weeks later, the reality TV alum heard rumors that Raptis was “telling people he’s single” and even “took a girl home” during a night out.

“I reached out and I said, ‘Hey, I got to announce that I’m single. I don’t want to be, like, hearing these things. I just got to rip the Band-Aid off and he convinced me to essentially give him another shot after that,” she claimed. “There was definitely a month period, maybe a teeny bit more but not much, that we were not communicating, no contact. We were done and then he heard my perspective and I told him, ‘This is how I felt.’”

Raptis then apparently asked Flanagan for the chance to “actually change” shortly before they formally moved in together. Their romance “recently” hit a snag when Flanagan got a message that encouraged her to reexamine what they had together.

“I’m just so confused by all of it,” Flanagan tearfully added. “I think the precedent that he would set in our relationship was, like, very, very strict … he would say things, like, ‘Never put yourself in a position that would jeopardize our relationship.’”

In the “burner” message, Flanagan received a tip that Raptis had been “highly disrespectful and [was] cheating” on her.

“I was like, ‘What the hell? What is this?’ There was something that I felt this entire summer and I was like things weren’t adding up because he would go [travel] and he’s not responding to me, he’s not texting me at night or random girls following him,” Flanagan alleged. “I would ask him about it and he would make me feel like it was my followers that were following him.”

Despite Raptis’ apparent denials, Flanagan did a “deep dive” to corroborate that his new social media followers were abroad at the same time he was. He also continued to deny that he even spoke to other girls while in the relationship.

By the time Flanagan moved into Raptis’ apartment, she discovered another woman’s jewelry in a drawer. He claimed it was purchased on Amazon for a Halloween party. She later met a woman in Miami who claimed to have hooked up with Raptis and gave Flanagan “receipts” from their interactions.

When Flanagan confronted Raptis, he continually denied the accusations.

“He runs into her in August and he’s still very handsy with her, hanging out with her family at her table,” the former attorney claimed. “I was like, ‘Damn, damn, damn.’ She’s sending me all the proof and I go to him and was like, ‘Do you want to be honest with me?’”

As similar situations continued occurring, Raptis allegedly would start to admit “very small” pieces of the truth.

“He was like, ‘Picked up a girl’s number in June at the bar in Philly,’” Flanagan recalled. “I was like, ‘OK’ and he’s like, ‘When I was at DC, I got another girl’s number, but I didn’t go to dinner.’ … I was like, ‘At this point, you would need to give me a lobotomy to literally believe anything that is coming out of your mouth.’”

Flanagan allegedly tried to break up with Raptis “several times this summer” once she started realizing his behavior was “sketchy.” He only accepted her pleas to call it quits when she asserted that she was “done.”

Flanagan is now working on healing.

“It’s still so fresh that I haven’t,” she said. “I know I will and I’ll be fine at the end of the day. I just know that I need to focus on myself and get myself back to a place where I was happy hanging out with my friends, do things that I love and that’s the only thing I can do at this point.”