Weber, who lives in Los Angeles, was first spotted with Flanagan and Dustin Kendrick (another franchise alum from Hannah Brown‘s season of The Bachelorette) in Chicago on March 25. The three hung out along the Riverwalk, an eyewitness confirmed to PEOPLE at the time.
Prior to being in a relationship with Flanagan, Weber was engaged to his season winner Hannah Ann Sluss. After their romance ended, he briefly reconnected with runner-up Madison Prewett.
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