Felicity
Felicity Porter, a sensitive and intelligent girl from the San Francisco Bay Area, decides to give up a slot at Stanford University's pre-med program to follow her long time crush to college in New York City. Things get even more complicated when she meets her dorm's resident advisor and they fall in love.

Season 1 · Episode 20 ·
Connections
Facing temporary suspension because of his unpaid tuition bill and pressure from his bookie over his gambling debts, Ben frantically sorts through his diminishing options.
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Episode 20 of season 1 of Felicity: “Connections”. Aired 1999-05-11. Watch it online free on ZapFlix.