Rainy Day Dreams is an episode from the second season of Garfield and Friends.
Garfield and Odie imagine an adventure on a rainy day. Meanwhile, Jon has a date with a woman who is secretly a home insurance saleswoman.
On a rainy day, a car pulls up to the Arbuckle residence, driven by a home insurance salesman and his assistant, Diana. Diana met Jon in the park and is planning to use his feelings for her to get him to buy an insurance policy. Inside, the roof is leaking and Jon is waiting for a roofer to come and fix it while getting ready for his rendezvous with Diana. Garfield is bored beyond belief to the point where he's willing to play fetch with Odie.
As Jon lets Diana in, he is hit by the ball Garfield throws for Odie to fetch and tells them not to annoy him or Diana. This leads the pets to go on an imaginative adventure into a cave leading to a mad scientist's castle. Odie's ball turns into the Klopman Diamond. Just then, they are attacked by a dragon. Garfield grabs one of the buckets patching the leak and dumps the water all over Diana. Jon scolds Garfield for that and puts him in his bed, leaving Garfield dejected for "saving" him.
While Diana is taking a shower and Jon is washing her outfit, Garfield and Odie imagine themselves inside the mad scientist's castle and avoid being noticed by Jon, who they see as the scientist's assistant Igor; Garfield points out that all scientists' assistants are named Igor for some reason. They find the monster (really Diana resting) and attack her. As they chase her around, they collide with Jon and her insurance papers come flying out, leaving Jon to realize why she came over in the first place. Diana decides to leave because it's not worth it with Garfield around.
Dejected, Jon worries he'll never find the right woman. The roofer (who happens to be a woman) arrives and happens to be a fan of Jon's work, much to his delight. As the two of them chat, Garfield and Odie pretend to sail off on the ocean in a boat, along with the fridge.
- Diana's boss