Safe to say Bachelor Nation didn’t see this one coming! More than one year after their messy split, Peter Weber and Kelley Flanagan spent some time together in Chicago.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.
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