Grace's accidental run-in with Noah, a curmudgeonly man she follows on Twitter, hints at a possible new love interest. Jack wants to look younger before meeting Estefan's family on Skype but makes a terrible first impression after overdoing the numbing cream before his facial procedure. Meanwhile, Will helps Karen protect the intellectual property rights of her most prized possession.

Now a certified psychic, Jack channels Rosario to help Karen open her heart to love again; Grace learns love means having to say you're sorry... to Will.

Jack's insistence that Will be nicer to his fiancé, Estefan, backfires when Estefan thinks Will is in love with him. In a hurry to buy her boyfriend Noah a Valentine's Day gift, Grace unknowingly knocks over a prominent figure while going after a taxi. And when Karen discovers that Noah not only writes her favorite romance novels but also plans to kill off the main character, she forces him to rewrite the story.

Grace returns from her European travels a new woman, but her elation is short-lived when she receives life-changing news. Karen teaches Will how to be better at phone sex. Jack has a yard sale to discreetly get rid of Estefan's annoying cuckoo clock.

Will discovers a way to finally get back at Jack for years of mocking his hairline. Grace is determined to prove to Mrs. Timmer she's strong enough to handle being a single mother. Karen squares off against Stan's brother in a poker game.