Christine Campbell is a recently divorced mother who runs her own gym, for other working woman who come to work out 30 minutes. She brings her boy Richard Jr. 'Richie' to his new, exclusive school on the first day of third grade, and finds it impossible to make him -or his in-living uncle Matthew- share in her excitement. She quickly finds the other mothers are wealthy and spoiled, looking down upon working class. Her ex Richard Sr. Campbell is there too, and not only suggests she brought the kid more for her own ego then for his future, but is seen on the parking lot...
Richie dreads going to his first swimming lesson. Barb sets Christine up on a blind date. At the restaurant while waiting for her date, she meets someone else waiting for his blind date. They get along better than their set up dates.
Christine is going on her fifth date with Burton, who is just a little bit too handsome for Richard's comfort. So he proceeds to sabotage their private time. Later, he comes to his senses and invites Christine and Burton on a dinner with him and the New Christine to make amends. Somehow, things go a bit wrong...
Christine and Burton have been on a date ten times and now it's time to take the next step. Christine introduces Burton to her child, but Burton shocks her by saying he'll do the same "when the time is right".
Having broken up with Burton, Christine forgets that she has switched nights of care-taking of Richie with Richard since she was going to see a play with Burton. She wants to switch back to the original schedule, but Richard has already other plans for the next day. So Christine concedes and ends up spending the evening alone, since Matthew is with his new, clingy girlfriend Natalie (who is never seen again after this).
Christine takes care of setting up Ritchie's birthday party herself after learning that she can't afford a party planner, which will certainly draw the attention of the school's other snobbier parents.
Christine is feeling anxious over the parents' night at Richie's school. Richard then just happens to suggest that Richie finally meet the New Christine. Christine turns to Matthew for opinions because she thinks Richie is not ready. Matthew's ingenious solution is not to answer Richard's calls - therefore the meeting can be postponed indefinitely! So Christine has to confess to Richard that it is actually she who is not ready.
Matthew goes through old family photo albums and finds only two photos in which he appears. Matthew becomes fixated to the idea that he's been left out. Then Christine points out that it is someone else in the other photo. Richard becomes angry at Christine, because she is so controlling about everything. Christine just sees Richard as helpless, in need of her telling how things should be done. Then she accidentally meets Hillary, Richard's old marriage counsel. Hillary asks how Richard is doing and Christine manages to force Hillary to voice her opinion that the ...
While at her son's school signing up to help at the upcoming fair, Christine runs into ex-boyfriend Burton, whose son recently enrolled. Seeing him rekindles her interest and her hopes soar when he seems interested in her, too.
When Richard forgets to complete Richie's mission project, Christine and Matthew scramble to finish in time for the deadline the next morning. Matthew is kept on hold for numerous hours waiting for the Internet text support to help with his problem.