Jay confessing his love to Alice at the end of the episode "Lady Hawke." He gives her a white rose and reads her a poem ("The woman I love will be my best friend. We'll make each other laugh, and I'll never be lonely again. Her name will be Alice, and she'll have a sweet Southern accent, and I hope she'll love me too.") Alice becomes completely touched, and she and Jay share a kiss.
CMOF, he accidentally sang "Super Freak" first.
Alice took it in stride.
Alice: Oh Jay, you're the sweetest man who ever called me a super freak.
After meeting Jay for the first time, Penny punches him in the nose because he gave a negative review of The Lion King. Jay tells Alice it's okay, because Rex Reed also did that to him. However, she immediately apologizes and kisses him on the nose. Awww.
The episode Siskel & Ebert & Jay & Alice centres around Siskel & Ebert breaking up. They each offer to make Jay their partner, which would be a dream job for Jay no matter which one of them he teamed up with. Instead, Jay Takes A Third Option and gets them to reconcile in a very touching scene.
It became a Tearjerker after Gene Siskel died in 1999, but it's even more heartwrenching now that they're both dead.
Marty and his girlfriend Carmen bidding farewell to each other as Marty prepares to leave Cuba.
Heartwarming In Hindsight: In December 2014, the United States and Cuba announced plans for normalizing relations between the two nations, meaning Marty and Carmen could be together again.
Jay and Alice's romantic relationship overall.
The episode where they met is kind of sweet. It's basically about two unlucky people helping each other out and falling for one another.
Even though he did it just to score off somebody who said he couldn't, Duke built an entire preschool - and spent a fortune on teachers - even though he only had one employee with a preschool-age child.
Franklin babysitting Penny... as he drives around the neighborhood in a monster truck and destroys a priceless piece of art. The scene where he exchanges smiles with Penny after destroying Guernica is as hilarious as it is sweet.
Jay saving Alice from going back to her country singer ex-husband. He starts singing to her, which is her major weakness, and Jay bursts in with an accordion singing an obnoxious Villain Sucks Song to break the ex's spell. It works.
The one single thing that Jay and his Jerk Ass ex wife Ardith still share, the love for their son Marty.
Penny literally writing a letter to Marty when he and Jay go off to fat camp.
When Jay breaks up with Olivia Hawke, he tells her she'll find someone who needs her even more than he did. Cue a Kindhearted Simpleton walking up to their table.
*Jay smiles as he sees Olivia and her new aquintance gazing lovingly at eachother*
Jay's romances tend to veer between humorous, creepy and sad, but the ones he had with Alice and Olivia are truly heartwarming, as they are one of the few people who looks past Jay's dull looks and caustic personality and sees him for who he truly is, a sensitive, highly intelligent man who has been mocked and pushed around his whole life.
While the eventual conclusion of the relationship was anything but heartwarming, the Beauty And King Dork scene from the pilot was both this and a CMOF as it tied in with an earlier joke about two kids painting the words "King Dork" on Jays car and Jay attempting to pass it off as due to him buying the car from the King of Finland to a valet.
Jay's attempt to be tactful when critiquing Valerie's performance. He tries to make it clear that though she's a terrible actress, he still loves her very much. Shame she didn't take it very well.
Jay's parents rebuild their marriage while stranded on a tropical island. Franklin's former self shines through from underneath his Cloud Cuckoo Lander behavior.
Jeremy Hawke's friendship with Jay, which is strong enough to that he risks his life dealing with Jay's psychotic stalker to save him.