Pooltime (2010)

Watch Pooltime: David is well-liked, middle-aged, successful, gay, and lonely but not alone. At his annual weekend pool party, his actions reflect this developing mood as he invites only his three best gay pals - Paulo, Roger and Virgil (all of whom are much like David himself: fairly handsome and fit, intelligent, gay, middle-aged and unattached). As David's thoughts want to head in a particular direction, outsiders keep intruding on his intimate gathering (a freeloading neighbor, a sister needing a babysitter, an old peach grower, and a mother who'd like to see her son connected). The one outsider who seems to be taking his sweet time butting in is the pizza boy with their food order.