It's been nearly 20 years since Jackie went on a date, but Marion tries to get her to meet men at a popular night club. However, when Marion's former grade school football coach comes for a visit, Jackie finds an eligible bachelor in her own living room.

Marion and his friend Carlton Banks discover that a boy is dating both Tiffany and Carlton's little sister, Ashley, at the same time, so they decide to teach the duplicitous guy a lesson in respect.

Marion takes a liking to an attractive neighbour, with whom Austin has been spending some time; meanwhile, Jackie delivers pizzas to earn extra money, and Heather practices hugging after her therapist tells her to be more friendly.

To Jackie's discomfort, one of Marion's former professional football teammates, Clayton Whitmore, comes to town to play poker with the old gang. That night, while the guys play poker, Austin sneaks downstairs to watch, and they invite him to play. Everyone is amazed by Austin's gambling prowess. Meanwhile, Heather manipulates Jackie into planning Heather's 30th birthday party -- and confronting the dilemma of finding ways to persuade guests to attend.

When Austin finds out that Marion is coaching a kids' football league with Marion's former grade school football coach Sam Wilson, he tries to impress Marion by making the team; and Sam accepts Austin hoping to date a grateful Jackie. Unfortunately, Austin is smaller than the other boys and plays terribly. Sam promises Marion that he will leave Austin on the bench during the game; meanwhile, Austin secretly tells Tiffany that he hates football but intends to stay on the team rather than disappoint everybody. On the day of the first game, half of the team stays home with chicken pox. Then one of the players gets injured late in the game, and Austin is the only alternate left on the team. He hides in the locker room, pursued by Jackie and Marion. Jackie realizes why Sam accepted Austin; Marion reassures Austin they're friends for life no matter what choices Austin makes. When Austin decides to play, he gets a chance to score a touchdown but becomes overconfident and is tackled. Meanwhile

Jackie ex-husband, Milton is thrown out by his new wife when he accidentally says Jackie's name during sex. Jackie refuses to allow him to live in her part of the home, but Marion lets Milton sleep in his room. Unfortunately, Milton drives Marion crazy with his annoying habits, and the next day Marion tries to force Milton back to Sasha. When Milton rents a romantic hotel suite, Marion calls Sasha to persuade her to reconcile with Milton. She refuses, causing a dejected Milton to lock himself in the hotel bathroom. After Marion calls Jackie at work, she rushes over and persuades Milton to come out of the bathroom. Grateful for her support, Milton hugs Jackie--just as Sasha enters....

After Austin gives Marion computer-aided financial advice, a computer mix-up gives Marion a large sum of money.