Weber spent time with Flanagan’s family in Illinois in July 2020.
“Still missing two of the kids but overall a successful first dinner night! ❤️,” she wrote alongside a photo of her boyfriend with her parents and brothers Jim, Tom and Michael. (Flanagan’s sister, Pamela, and brother John were missing from the get-together.)
The pilot later referred to the trip as “the hometown that should’ve been ❤️.”
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