Complex sentence: John lost his medical license for a time and to get revenge, courted Lisa, then, during their engagement party, sent a taped message dumping her, which embarrassed her in front of the entire town.
Split into simpler sentences: John lost his medical license for a time and to get revenge, he courted Lisa. Then, during their engagement party, he sent a taped message dumping her, embarrassing her in front of the entire town.