After Jesse doesn't accept Diego's proposal, he heads to California to take his new teaching job. Then we go four months into the future, where Jesse is studying to be a nurse and gets a new job as a nurse's aide at a local college. Diego then makes a surprise return when he is given his old job back.
Jesse is excited to join Dr. Dan and Kurt in a car pool, but it ends in disaster. Meanwhile, Linda, who has been living in Diego's house since he went to California, refuses to leave.
Jesse takes time out of her busy day to console her friend, Carrie, who insists she has an important problem she needs to talk to Jesse about. An angry Jesse accidentally insults Carrie when she learns that this urgent situation had to do with a monkey flinging poop at her. Meanwhile, Linda who is worried that Little John is becoming a geek, tries to interfere.
Jesse plans a small barbecue for her friends, but is then forced to invite her bosses. Jesse also invites Diego, when she notices that he's been depressed lately. The barbecue party, however, is destroyed when Jesse and Diego's personal feelings get in the way of everything else, and Diego runs off with the grill.
Jesse is growing tired of Kurt's hostile attitude towards her and later finds out that he has even been spreading rumors about her stealing from work.
When Little John is away, Jesse has the house to herself. However, she has to keep avoiding her boss' request to come in to work by pretending to be sick. Also, she and Diego share a moment of passion while fixing her flat tire, which yet again ends in a proposal from Diego.
With Diego still upset that Jesse has once again rejected his marriage proposal, Jesse tries to win her way back into his heart by considering proposing to him this time.
Jesse is involved in a love triangle between Diego and his ex-fiance, Irma.
Jesse, trying to lift everyone's spirits, throws a Christmas party for her friends and co-workers but things do not go as planned.
Jesse has trouble dealing with a squirrel, while Diego has a battle of his own to deal with when Little John and his friends initiate a snowball fight.
Diego gets a taste of his own medicine, when Irma proposes to him when that's the last thing that he wants.This causes him to know exactly how he made Jesse feel and he apologizes and gets back together with her. Meanwhile, Kurt suffers from a back injury and ends up in the hospital.
Jesse has trouble finding her stolen car.
Linda doesn't want to face her classmates at an upcoming high school reunion because she is disappointed with her success in life.
Diego's announcement of his want for a big family causes Jesse to think back to her stressful pregnancy with Little John.
Diego's new mustache bothers Jesse, but he refuses to shave it off.
Jesse thinks that a lab coat will get her more respect from the patients. Meanwhile, Diego's house catches fire.
Diego's fridge is hauled to the dump. Only problem is that is where he kept his passport, so he and Jesse must try and find it.
Jesse, thinking she has the house alone invites Diego to spend the night. However, her son, Little John, walks in on the two which horrifies Jesse.
Jesse learns that the man who had the job before her earned more money because he was a phlebotomy's and drew blood. She has Kurt try and train her on how to draw blood, but she ends up passing out in front of her patient.
Diego who once again faces deportation, agrees to stage a fake marriage with Linda so that he can stay in the country. Jesse is fine with this at first, but the more she thinks about it, the more it bothers her.