Tear Jerker / Free Spirit (2014)

• The sequence in the Pilot where Jessie's friend ditches her for some snobbier, more popular kids ends with one of those kids taking a photo of Jessie crying for a phone wallpaper.
• Winnie's failure in "Wish Gone Amiss" to answer Gene's Armor-Piercing Question in a manner that doesn't upset him even more strongly. Also, imagine how strongly Gene must have tried to hide his anguish over his parents' divorce in order to go almost five comics without asking that question to Winnie.
• "Love That Winnie" has Winnie fear that the Harper kids only love her so they can take advantage of her magic. Her attempts to prevent Gene from getting away with breaking Thomas' trophy sour her friendships with both Gene and Jessie. Distraught, Winnie decides to return to the witches' realm, but can't bear telling the kids, "goodbye". Even after she retracts that decision, she appears unable to restore the kids' memories of her. The Power of Friendship eventually restores them, but the promises Winnie makes both beforehand and afterward to always protect the kids still feel bittersweet.
• "Robb Harper Presents The Donald Trump Glorification Special" has a scene that could count as both this and a Heartwarming Moment, after Winnie, Jessie, and Gene consider the Bad Futures that could ensue if Donald Trump becomes president:
  Gene: Winnie...are we gonna die?
  Winnie: (solemnly hugging Gene and Jessie) YOU won't!