1. Pilot  

First aired: 3/27/2001    Production Code: 101

Joan Gallagher, a high school teacher, is caught off guard when Jake, a banker, proposes to her after only six weeks and nine dates. After she doesn't answer, he realizes that he's more committed to the releation than she is. Joan then turns to her friend who happens to be a psychiatrist, Dr. Ruby Stern, for advice. Joan goes to see Jake at his apartment and finds that he's not as nice as he had been earlier. At Joan's urging, Jake withdraws his proposal and decides to continue their relationship a little more slowly; Meanwhile, Joan's friend, Betsy, also a teacher, continues her secret romance with fellow teacher, Mark. Joan meets her new teaching aide, Alice Adams, whom she instantly likes.

2. Sex Talk  

First aired: 4/3/2001    Production Code: 102

In an effort to find out what possible problems may lie ahead for her relationship with Jake, Joan sets out to uncover them now rather than waiting for any explosions later. When she asks Jake if she is the best lover he ever had, and doesn't get the response she was hoping for, Joan attempts to learn new ways of making things better in that department. Meanwhile, Betsy knows she must move on from her relationship with Mark because it's only bringing her pain. The only way she can think to do it is to have Ruby start dating him in order to distract him. Unfortunately, things go much too well in Mark's eyes and he's suddenly smitten with his ex's best friend.

3. The Proposal  

First aired: 4/10/2001    Production Code: 106

It appears that Betsy is getting very antsy to have Mark propose, which he is a long way from doing. So she takes some of Jake's advice: act like you don't care and watch him come crawling. Betsy gets the reaction she wanted when Mark comes crawling back and she convinces him to propose. Meanwhile, Joan feels deeply betrayed by her English class when she discovers that they cheated on a test. And Ruby gets a book deal to spread her wisdom, and a pesky publicist along the way.

4. Joan Meets the Parents  

First aired: 4/17/2001    Production Code: 108

While out to dinner with the girls celebrating Alice's 25th birthday, Joan runs into Jake who is having dinner with his parents -- the parents she has yet to meet. She decides to play it cool and decides to go over and say hello. Things do not go well. After making a poor first impression, Joan invites them over for dinner at her place to try again, against Jake's wishes. With Alice as a buffer, Joan sets out to make friends with Jake's parents. After Jake's parents spend the evening insulting and ignoring Joan, Jake yells at them and takes them off to the airport, where Joan shows up and changes their impression of her and also fixes Jake's relationship with them... all with the help of a camera.

5. Free Speech  

First aired: 4/24/2001    Production Code: 113

Just as Joan's high school Speech Team wins the Illinois Speech championship and gets ready to head to San Francisco for Nationals, word comes down that the school board is cutting funds for all of their teams and clubs. A competition among club sponsors, including Joan, Mark, Betsy and Alice, ignites with everyone trying to pitch to the board why their club should not suffer the loss. When the dramatic and charismatic basketball coach has his turn at the podium, it's obvious by his "presentation" that the rest of them don't stand a chance – until he realizes others are just as deserving of the money and he instead gives it to Joan; Meanwhile, a student develops a crush on Ruby and isn't shy about letting her know.

6. Joan's Sister Visits  

First aired: 5/1/2001    Production Code: 104

Joan's nerves are going at full-speed with the thought of Jake meeting her sister Ann who is due to come into town for a visit. The pair meet and hit it off, but all good moods come to a crashing stop when Joan realizes Ann is having problems at home. Ruby gets pleasantly distracted by a "silent cowboy type" and Betsy can't stand to be away from Mark any longer and works for a reunion between the two.

7. Maeve  

First aired: 5/8/2001    Production Code: 107

Joan and Jake's relationship is tested when a sultry seminar leader comes onto Jake while on a business retreat. When Joan finds out that Jake may face temptation, she falls apart at the thought of his infidelity. Ruby, Betsy and Alice come together to get her through her "breakdown" until Joan realizes there is nothing to worry about. She's got a good thing.

8. Ruby Doobie Doo  

First aired: 5/15/2001    Production Code: 111

Sensing that Jake is in a "funk," Joan encourages him to get some professional counseling, a la Dr. Ruby Stern. Against his better judgment, he agrees to go and talk to Ruby, although it feels strange to divulge his most intimate thoughts to Joan's best friend. During their session, it's Ruby who has a breakthrough, realizing that somehow along the way, she never pursued her first love of singing, for fear that she would fail. Concerned that she would never be the best, she never tried. In an effort to push Ruby past the point of fear, Joan sets up an opportunity for her to perform at an open mic club.

9. Betsy's Wedding  

First aired: 5/22/2001    Production Code: 110

The big day arrives for Mark and Betsy, who have planned to finally walk down the aisle. However, a massive snowfall in Chicago sets out to destroy their dream day, until Joan intervenes to make it all work out, as usual. With Mark stuck at the church with Jake, Alice, Mark's half-brother Herman and the minister, and with Betsy stuck at Joan's with Joan and Ruby, they incorporate new methods to make their union happen at all costs: THE PHONE. It's not the most romantic way, but it gets the job done!

10. Mr. Roboto  

Production Code: 103

Betsy becomes depressed over Mark, so Ruby decides to throw her a party to cheer her up -- complete with tons of eligible bachelors. But just as Betsy begins to look on the bright side at the party, Joan and Jake have a falling out over a comment Joan makes concerning his personality.

11. Quid Pro Quo  

Production Code: 105

Joan and Mark find themselves in trouble with the police. Due to Joan's pushing, Mark drives faster in order to get to Joan's niece's recital on time and ends up getting pulled over. Thinking he's doing the smart thing, Mark slips a twenty in with his license and registration and is promptly arrested for attempting to bribe a police officer. After spending a rough night in the slammer, Joan's guilt at pushing him to drive fast gets the better of her and it's now her goal to find Mark good representation to get him off the hook. She then realizes that not only is Jake a smart investment banker, but he also passed the Bar and can practice law!

12. Joan Sets Up Alice  

Production Code: 109

Jake introduces Joan to his friend, Ben, who happens to be a chef looking to open his own restaurant. Realizing what a great adventure this could be, Jake and Joan decide to invest in Ben's dream and start the ball rolling on making his dream come true. Meeting Ben also sparks an idea in Joan…to set him up with Alice who hasn't had the best of luck with men lately. Ben and Alice meet, only to find they have a lot in common, and set off on a whirlwind courtship that suddenly comes to a halt when Ben realizes he has too much to battle right now as it is without having to worry about a new relationship. The news devastates Alice, until Mark, in all of his wackiness, intervenes and turns things around!

13. The Curse of the Sweater  

Production Code: 112

After going through old photo albums, Jake learns that Joan used to make hand-knitted sweaters for all of her past boyfriends. He pushes her to make one for him but she adamantly refuses. After much pushing, Jake finds out the real reason she won't make him one is because when she did in the past, she'd end up having a huge fight with the boyfriend which resulted in their breakup. Not wanting to repeat history, she thinks it's better to avoid altogether. In typical Joan style, we learn that it wasn't the sweater that broke up those relationships, but Joan's insecurities.