Jennifer was reportedly dressed "casually" in jeans with her hair down as she rode in the back of her security detail's car, arriving to John's crib. She was rocking a big overnight bag. This "small gesture" is reportedly a big step in their relationship.
When they dated the first time around John would always go to Jen's house because John has a typical bachelor bad; it needs new paint, it's beat down with overgrown trees and he doesn't have items in the fridge other than "a six-pack of beer."
source, source
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