It’s all shown in Flanagan’s Instagram exchanges with the parents America loves to hate.
Flanagan reached out to Weber’s father (Petet Weber Sr.) to wish him a happy birthday. It seems they’re so close that Weber’s dad has a nickname for Flanagan. “Thanks so much for the wishes Chop Chip,” he wrote. “Miss you guys.”
To rewind a bit, Weber sent Flanagan, a Chicago attorney, home on The Bachelor before hometown dates. He ended up engaged to Hannah Ann Sluss for a month, then split from her to reunite with Madison Prewett. Their relationship only lasted two days after they went public, seemingly because Weber’s family strongly opposed their relationship.
Weber apparently doesn’t have that problem with Flanagan, who he was first spotted with at the end of March. He’d flown to Chicago, it seems, despite Covid-19, and the pair were photographed being incredibly flirty along the city’s iconic lakefront. It was just a day before Chicago shut down the public park, so Weber and Flanagan reported to what seemed like her apartment to quarantine together. We know this because of Weber’s cringeworthy TikToks that show them together for some time.
Again, Weber and Flanagan claim they’re not together, according to Weber’s comments on The Viall Files podcast in early April. “Are we dating? No. Do I love spending time with her? Absolutely. We’re not dating. Could I see that in the future? Yeah, of course,” he said. “I’d be extremely lucky and very happy if that happened.” He followed up by saying he’s taking it slow because of his recent broken engagement.
That hasn’t stopped Weber’s judgmental mom from jumping on board with his connection to Kelley, too. America thought no one would ever compare to Sluss in the mind of Weber’s mom, Barbara, but apparently, Flanagan is in good graces. Barbara has commented hearts on Flanagan’s Instagram and even said things like “We need to do lunch and go shopping for the day.” It sounds like comments to a future daughter-in-law to us.
The world will need to wait to see if Flanagan and Weber make things official, or last past the quarantine state of dating.
