Robbie introduces Lucy to his friend Hugh, feeling she should date again, but gets jealous enough to separate them with lies. Matt stands up against the free clinic's staff and gets Hank to overrule Dr. Kent's diagnose-and-operate routine. Feeling incompetent as a waiter at Pete's Simon resigns, but he gets promoted because of his business-planning skills. Cued by Billy via George, Wilson and Mary (who is failing in firefighter training) realize it's time to decide whether to commit to becoming a family.

Robbie and Lucy gather the courage to tell everybody about their affair, only to find they all knew and don't really care. Without the thrill of sneaking, their first date fizzles. Ben Kinkirk and Mary both pass the firefighters course, but their meeting on whether to celebrate with classmates messes up Mary's reconciliation with fiancé Wilson., and Billy's questions make Wilson decide against her plan to elope. Matt discovers that Hank and Julie are planning a divorce, and Eric and Annie try to find out why and see if they can help fix it.

Robbie's apparently firm happiness with Joy kindles envy in Matt, who is now so in love with wedding plans that he vows that his next steady date must be *the one*. Being commandeered into clinic duty, Matt misses his date with a promising candidate but he also meets a fellow med student, Sarah Glass, daughter of Rabbi Richard Glass. Sarah insists that they must meet each other's parents. Although both parental pairs plead against a mixed-religions marriage, the lovebirds soldier on.

Preparations for Matt and Sarah's wedding are being made and things aren't going the way Eric or Annie planned. Matt decides he will convert to Judaism after a discussion with Sarah's dad who convinces Matt that he can convert on the wedding day much to Eric's dismay. Annie panics when Sarah's mother tells her to expect 100 kosher guests to her backyard pot luck dinner. Ruthie and Simon begin to resent Robbie being in the house. Ruthie wants her bedroom back forcing Robbie out now that Matt will be moving out and Simon gets upset that Matt chooses Robbie to be his best man and Sam and David call for Robbie instead of him. Lucy gets upset that Kevin won't come to Glen Oak for Matt's wedding and Ben decides to propose to Mary after Mary starts giving him the cold shoulder. Eric and Sarah's dad the Rabbi go head to head and it seems Matt and Sarah's wedding won't go ahead after all.