It's Better to Have Loved and Lost It... is the 5th episode of Season 4 of The Fresh Prince Of Bel-Air.
Summary[]
Carlton meets Jo Ann, a beautiful woman on the college campus. They end up spending the night together and Carlton finally loses his virginity. This also helps give him confidence as he prepares again to apply for Princeton. However, Carlton's shot at greater merriment is short-lived, as Jo Ann turns out to be married (to a man who could help Carlton get into Princeton) and reveals to Carlton that she was actually using him for a one-night stand.
Meanwhile, the ethics committee is digging up dirt on every judge in town and Philip worries that the slightest indiscretion could cost him his Job, Geoffrey ends up panicking the most and shows a tape to the family, revealing that he cheated in the 1976 Olympics, taking a cab in order to reach the stadium before the other runners. Because of this, he had his gold medal taken by the Queen and became so ashamed of what he did to his nation of Great Britian that he went into hiding and fled to the United States. The family laughs it off and assures Geoffrey that it won't ruin anything.