How Not to Live Your Life: Don Dates a Homeless

Sitcom about Don, a desperate lothario. Don meets a homeless girl in the street begging for money and strikes up a rapport. Whilst out with Sam the next day he confesses to finding her attractive. Sam jokingly dares him to ask her out, so he does. Sam is continuing to put pressure on Don to make more of an effort with her boyfriend Brian, culminating in a boy's night out with Don, Eddie and Brian.