Photos of the 28-year-old pilot and his ex, Kelley Flanagan, surfaced on Wednesday, showing the pair goofing off together at Chicago Riverwalk. Weber carries Flanagan in several of the pics, while others show them hanging out with his fellow Bachelorette alum, Dustin Kendrick.
Weber's playful outing with Flanagan comes less than two weeks after his split from Prewett. The Bachelor season finale, which aired March 9 and 10, saw Weber propose to Hannah Ann Sluss, then end their engagement. He revealed on After the Final Rose on March 10 that he and his runner-up, Prewett, were going to give their romance another shot -- but they announced their breakup just two days later, on March 12.
In paparazzi video obtained by ET the next day, Weber insisted that his breakup with Prewett had nothing to do with his mom, Barbara, expressing her strong disapproval of their relationship. She had said on AFR that the pair were "not gonna work."
"This is stuff between Madi and I, solely, 100 percent," Weber explained. "And people will have their opinions but this is just between the two of us, and it's just a mutual respect and love. That's all."
Barb, however, was a big fan of Flanagan. In a March 11 interview with ET, the Chicago-based lawyer opened up about meeting Weber's mom at the Bachelor finale taping -- and revealed what Barb said to her.
"She stans Kelley, which I just learned, which is really funny," Flanagan said. "I saw her at the finale. She would not leave the finale until she met me."
While Flanagan said that she and Barb "just had small talk" and exchanged hugs during their meeting, she revealed that Weber's mom told her, "You're beautiful, I love you. I was your fan since day one."