黛安在前一晚喝多了，并在醒来后担忧自己已跟不上时代。但是，她仍然发誓要教侄子如何生活。

黛安为公司举办的测验做准备。丹尼尔搬去与她同住并开始求职，却不幸与城中的野生动物狭路相逢。

排骨节上的老年福利刺激到黛安，她要出马证明自己青春犹存，不料却遭遇了难题：她确实老了。

黛安和邦妮的父母大路和佩格飞回来看熊队对战包装工队的比赛，参加车尾派对。派对上，敌对家族之间的宿怨重新被激发。

丹尼尔想献出自己的初吻，于是盛装出席在罗斯科酒吧举行的万圣节化妆派对。黛安在派对上爆出了吉迪恩的大秘密。

马克无意间听到邦妮说他无法跑完芝加哥马拉松。丹尼尔要在马拉松终点与创意果汁的首席执行官会面，但他却迟到了。

85 年的熊队将在牛肉节重现超级碗曳步舞，黛安因此激动不已。然而，她的儿子麦奇却在同一个晚上安排了晚宴。

圣诞节前夜，每个人都有各自的安排，黛安却独自一人。不料，一段出故障的电话留言却让她的家人陷入恐慌，前去一家家医院中寻找她。

Diane seems to find a kindred soul in a new neighbor. Bonnie and Mark want to have a new baby, while Daniel is shocked while taking an art class.

Diane uses a dating app and matches with someone she least expected. Daniel starts seeing a professional baseball player for the Chicago Cubs.

Daniel doesn't want his Aunt Diane to know who he's dating because he fears what she may do. Diane tries dating a nice guy, for once.

Diane tries to find a way to cheer Daniel up, but they then get into a big fight. Mark goes to stay with Diane after he and Bonnie argue.

Diane wins a free mammogram and needs to see a specialist after the results, so Bonnie helps out. Daniel tries to overcome his anxiety over driving.

Diane partners with Gideon to sell homemade lotion but its secret ingredient proves costly. Bonnie wants to return to work as an event planner.

Gideon wants to take their lotion global, but Diane has second thoughts. Mark and Bonnie have financial trouble and may need to sell the condo.