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Jack learns that Stitch's new boyfriend is jealous of her feelings for him, so he must decides if he should take the next step. Meanwhile, Terry is sick this time and Tony must take care of her.
Jack discover that Tony's new girlfriend is two-timing him. Meanwhile, Mason seeks help from Darren after Terry won't let him drive.
Tony interferes Jack's work decisions when he lands a big job in the affluent Beachwood neighborhood. Meanwhile, Darren keeps leaving Ellis with Stitch and Terry is getting Tony ready for his physical.
Jack tries to reconnect with a high school crush and Darren has an idea stolen after they take a job in a corporate office. Also, Terry meddles in Mason's relationship and Tony is uncomfortable with his girlfriend's style.
When Tony has a heart attack he must hand down the family business to his son Jack.