5. Homeboy, Sweet Homeboy

Complete story — includes the ending

Will gets a visit from an old friend named "Ice Tray" ( Don Cheadle ), who, to Vivian and Philip's dismay, warms up to Hilary. Philip and Vivian try and discourage Hilary from falling in love with him by finding great warmth to the idea until she jokingly says she just married him to gauge their reaction, which is an outrage. Will confides to Vivian just how good a friend Ice Tray had been to him when he was the only studious kid from a class of dropouts in Philadelphia. Vivian says that it is commendable Ice Tray stuck up for Will, but rhetorically asks how concerned was Ice Tray for his own welfare. Will revealed that Ice Tray had no one around for him and eventually stopped caring about himself, adding on that he [Will] too would've been like that if Ice Tray wasn't there for him.