Carl, Mike and Samuel take a road trip to Memphis to meet Carl's mother for the first time.
Samuel wants to be a standup comic. Meanwhile, Molly offers advice to Harry which leads to him challenging his protective mother.
At Mike's urging, Molly grudgingly goes to a therapist.
Molly meets her literary idol, J.C. Small, a cynic who advises her to write about things in her life that she wouldn't want people to know. Meanwhile, Mike invites his mother over for dinner in an effort to cheer her up.moreless
Molly decides writing a crime novel will be her new career, so she goes on a ride-along with Mike to research a book she wants to pen.
Molly makes a huge decision to stop her career as a teacher and delve into writing.
When Peggy breaks up with Patrick, Mike tries to reunite them; as a tornado reaches Chicago, Molly and Mike reveal important news to each other.
Molly is so focused on directing a school recital that she doesn't realize a fellow teacher is hitting on her. Meanwhile, Vince convinces Mike to join him in an unusual money-making scheme.
Mike goes on a junk food binge to cope with missing Molly while she is out of town for a teacher's conference. Meanwhile, Carl contemplates leaving Chicago after learning heartbreaking news from James.moreless
After learning that Joyce gave up her artistic talents when she became a mother, Molly decides that she and Mike need to pursue new hobbies before becoming parents, so they take up roller skating.moreless
Mike's birthday wish is to have his wife and mother get along, but Molly and Peggy butt heads more than ever as they try to plan his birthday party together. Meanwhile, Samuel and Carl compete for the same woman.moreless
Molly joins her sister on a spring break road trip to party with Victoria's friends from junior college. Meanwhile, Mike pulls strings with his boss to get special overtime assignments in hopes of making extra money.moreless
Molly reveals some juicy information about her past to Mike. Meanwhile, Carl and Samuel hold a St. Patrick's Day party hoping to meet women.
Following a disagreement with Mike at the mall, Molly goes on a shopping spree.
Mike decides to take things into his own hands and find out if he is fertile enough to make a baby with Molly. Meanwhile, Vince starts working as a door-to-door vacuum cleaner salesman.moreless
Harry decides to ask Victoria out on a date for Valentine's Day, and she surprisingly accepts. Meanwhile, Carl and Samuel try to pick up women at the laundromat.
Mike starts construction on the basement in the Flynn house, but it turns out to be a more of a challenge than he thought. Meanwhile, Samuel becomes Carl's new roommate.
Mike's special plans for Molly's birthday are put in danger when he unexpectedly eats psychedelic food made by Victoria's friend.
In hopes of easing their chance to make a baby, Molly talks Mike into giving up caffeine and eating healthier, causing withdrawal issues for both.