Will & Grace
Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating, sex, relationships and their careers, butting heads at times but ultimately supporting one another while exchanging plenty of witty banter along the way.

Season 2 · Episode 24 ·
Ben? Her? (2)
Forced by his boss to betray both of his friends, Will quits--only to discover that everything isn't as it seems. Frustrated, he leaves a lost Jack and Grace behind and ends up on a tropical island without a care in the world. Until Ben shows up.
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Episode 24 of season 2 of Will & Grace: “Ben? Her? (2)”. Aired 2000-05-23. Watch it online free on ZapFlix.