Season synopsis
Contains spoilers for this season and earlier seasons.
Season 7 opens with Charlie trying to prove he is committed to Chelsea, even arranging a wedding date, while his old reflexes keep testing their partnership. After he betrays her trust and then becomes jealous of her relationship with lawyer Brad, Chelsea ends the engagement. Charlie briefly marries Betsy in Las Vegas, learns she already has a husband, and later sleeps with Chelsea’s friend Gail; those choices deepen the break rather than restoring the couple.
Alan resumes his relationship with Melissa, but their attempt to share the Harper house quickly collapses under clashing boundaries. He later takes work from his mother Evelyn and falls for Lyndsey, the mother of Jake’s new friend Eldridge. Jake’s girlfriend Celeste breaks up with him after Charlie encourages him to cheat while she is away, and Alan and Lyndsey’s relationship begins as the boys’ friendship grows. The season keeps the family’s romantic upheaval close to Jake’s increasingly independent teenage life.
By the finale, Charlie has lost his driver’s licence after covering for Jake during a traffic stop, so Jake becomes his chauffeur. Charlie sends Jake to Chelsea’s birthday with a forgotten gift, and she leaves the party upset before finding Charlie being arrested after he crashes into a police car. Their engagement is already over, and this final encounter does not reunite them; Chelsea and Charlie do not marry, leaving him without the settled future he had briefly planned.