Multiple Timelines; One Locked, One OTA (Tag Cuddy)
So, as it's established that time isn't a fixed construct, House is in two places at once; or, rather, there are two timelines happening at the same time:
One night, he was in his bed, tossing up the very-familiar oversized tennis ball up with his cane, while waiting for Ray and the girls to arrive. Or, waiting for Terry to get fed up and bring him the damn pot already. Either way, he'd be good.
The next night- for better or worse- he was down at the bar, nursing a scotch while waiting for his former boss to meet him for dinner. He hadn't spent much time with Cuddy, for a couple universes now. Well, better late than never, he figured.