|It's Better to Have Loved and Lost It...|
|Original Broadcast Date||October 11, 1993|
|Written by||David Zuckerman|
|Directed by||Shelley Jensen|
|Preceded by||Father of the Year|
|Followed by||Will Goes a Courtin|
It's Better to Have Loved and Lost It... is the fifth episode of The Fresh Prince of Bel-Air's fourth season which was first broadcast on October 11, 1993.
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, someone is attempting to get dirt on local judges and Geoffrey fears his past could damage Phil's reputation. Geoffrey shows a tape to the family, revealing that he cheated in the Olympics in the 1970s, taking a cab in order to reach the stadium before the other runners. Because of this, he has his gold medal taken by the Queen and becomes 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 off the tape and assures Geoffrey that it won't ruin anything.