When acting girly to get a cute boy to ask her to dance fails, a mysterious witch makes Tess’s off-the-cuff wish to become a boy a reality, leading Tess to discover that being a member of the opposite gender isn’t easier most of the time. Meanwhile, Spencer said that he ate all the halloween candy so now he and Jack have to go trick or treating around the block to get candy.

Every year Jack tries to get the family to pose for the perfect holiday card photo and every year his plan fails. So when the kids disappoint him yet again by botching the photo shoot, Tess feels guilty and makes them all swear to stop fighting, as the ultimate Christmas gift for dad. The strain of bottling up their frustration leads to a big fight, and Spencer, afraid his misbehavior will land him on Santa’s naughty list, runs away from home. Tess tracks Spencer down at the mall, where the Santa imparts some pretty good wisdom, helping them all enjoy a better holiday season.

After Tess is alone on Valentines Day, she and Allie come up with the idea of "Girl-entines day".

Tess is determined to keep Jack on as her wrestling coach, even if it means helping him land the dreaded position of Vice Principal in charge of school discipline.

When the school district refuses to replace the wrestling team's dilapidated mats, Tess produces a video that changes their minds, only to discover that an allergy to the new mats makes them more dangerous to her than the old ones.

When acting girly to get a cute boy to ask her to dance at the school's Halloween party fails, a mysterious witch makes Tess's off-the-cuff wish to become a boy a reality, leading Tess to discover that being a member of the opposite sex isn't always easier.

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Tess sells Gabe's song to a famous musician without getting his approval first.

Tess's reputation takes a hit after Jack forces her to show a dorky new student around the school, and she tries to fix the problem by making the geeky student cool.

When Jack wants the kids to spend all their time together with him over Spring Break, Tess invites Grandpa to keep her Dad occupied, and learns a valuable lesson about appreciating parents and the short time you get to be with them before it's too late.

Allie, Jack and the boys search for a tape to help calm Tess down during exam week.

Tess's teacher is going on vacation and needs someone to look after his pet turtle, so he chooses Tess to look after it. As she does, she discovers the turtle is expecting to lay eggs!