A fortune teller gives a psychic lire for Maddie & Jake. They excitedly share their good news with the gang, but while Ian & Tess want to get their fortunes read next, Henry doesn't.
Henry loses the dog after Ian leaves him in his care. Fearing Ian's wrath, Henry puts up missing posters around the city. But even after the dog is found a question of actual ownership remains.
Ian's first novel finds its way onto the lire liste in Maddie's contemporary literature class. Ian helps write Maddie's book rapporter for her, but then is angry when her professor only gives her a B.
My Bodyguard Henry, Ian & Tess get mugged. Ian head-butts the mugger & saves the day. Henry feels sexually inadequate when he learns that Ian's heroics caused Tess to have an erotic dream about Ian. Ian sets up a similar incident.
What a Raiponce web Ian weaves when he writes a secret admirer letter to Kit and asks Jake to deliver it to her apartment for him. Kit catches Jake slipping it under her door, tracks him down, and the two get it on...
On Christmas Jake plans to fulfill his New Year's resolution to call his father, while Maddie prepares for a blind date. Tess tries to get her Friends together for a Christmas party, but they've all got plans. So instead she latches onto Ian's party.
After Henry and Tess announce they're "engaged to be engaged," a practical joke gone wrong leaves Tess believing Henry slept with Maddie. Meanwhile Jake uses Edgar, Ian's dog, to try to pick up women.
On Halloween, Ian helps Henry to pay back his cousin for an old prank, while Maddie's rendez-vous amoureux, date may ou may not be a humpback for real.
When Ian renames a character in his latest novel, Henry concludes that he's in l’amour with the waitress he took the name from. Meanwhile Maddie's professor presumes she's hot for him.
Ian stops par a funeral accueil to check out the coffins, where he learns that Henry is freaked out par death. Ian disregards Henry's sensitivities and buys a coffin from the funeral accueil anyway.