Season 1 - Episode 36

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Hercules' heart is broken when his girlfriend (of only three days) breaks up with him, so Phil takes the kid on a trip designed to take his mind off of things. But Herc meets Lavinia on this trip, who is eager to get married...to him...and not only is he faced with rejecting her, but her previous boyfriend just happens to be the same guy Herc conquered that very trip.