Us Weekly can confirm the 31-year-old former Bachelor and the 30-year-old attorney attended the Chicago Cubs game together on Wednesday, August 10, watching the home team beat the Washington Nationals.
Weber and Flanagan dated for nearly one year after his season of The Bachelor finished airing in March 2020. While the pilot sent Flanagan home ahead of hometown dates — proposing to Hannah Ann Sluss and then ending the engagement because he still had feelings for Madison Prewett — they reconnected post-show.
After several months together, Weber and Flanagan announced their split on New Year’s Eve in December 2020 before rekindling things in early 2021. They broke up again that February.
“We had a great Valentine’s Day together. And then, again, there were just like little things. … It ended really badly,” Flanagan said on the “Chicks in the Office” podcast in May 2021. “I essentially went off on him. I ended up leaving New York and going to one of my girlfriend’s houses and hanging out with her. He texted me, I didn’t respond and then found some news out that I wasn’t happy about. We still had each other on Find My Friends. … I went off and essentially said, like, ’Get the hell out of my life.’ It ended really badly.”
The former Bachelor contestant went on to hint at “non-negotiables in the relationship” that led to their demise.
“You come off [the show] and you’re like, ‘Oh, some of your hobbies don’t align with mine.’ It’s not a bad thing, [but] he loves Pokémon cards and he loves playing video games and he loves going out and partying,” she added. “There was a while where I was trying to convince myself that that’s what I liked and I was like, ‘Alright, Kelley, let’s be honest with yourself. Does that add up for you?’”
Weber responded to Flanagan’s remarks on his own podcast, “Bachelors in the City”: “We were different in a lot of ways. I will never apologize for liking Pokémon cards. … Maybe she was just playing along to make me happy.”
More recently, Flanagan hinted that Weber wasn’t marriage material.
“Peter and I had a lot of fun, but I don’t know if I looked up to him in the way that I wanted to look up to my spouse,” she said on the “Talking It Out” podcast in May. “I have this with my brothers and my dad, where if I’m in a moment where I need some sound advice and look for who to go to on important decisions, but with Peter, it was just fun and games. I could have fun with him but I wanted more of a man that I look up to. I just didn’t look up to Peter in the way that I always hoped I would look up to my husband.”