Tear Jerker / 13 Going on 30

• When Jenna thinks all is lost.
• Jenna breaking down over the big grown up world of hurt to Billy Joel's "Vienna."
• Jenna gradually finding out what a Jerkass she's been as an adult.
• Poise shutting down in the end. Especially when things were just beginning to get better for them, right before Lucy decides to be petty, and sell out Jenna's redesign pitch out of jealousy—therefore finishing what Jenna had originally started, and putting all the employees at Poise unemployed.
• What Matty went through in the original timeline: He and Jenna were next-door neighbors who probably knew each other from toddlerhood and became seemingly inseparable besties. Then one day, Jenna decides to become a "Six Chick" and not only abandons Matty from then on, but even mocks and bullies him at times. This gets bad considering he had feelings for her when that happened. In a single moment, what was once an absolutely beautiful friendship, turned into something that left a gaping hole in Matty's heart that wasn't filled for years. He did of course move on as an adult and ended up doing fairly well for himself, but that must've been an emotionally traumatic thing for a 13-year-old to endure.
• Jenna confessing her love to Matt right before his wedding to Wendy. He admits that he's loved getting to reconnect with her, but they can't just ignore the last 17 years and he's moved on. Jenna tearfully accepts it, and is given the dream house Matt had made for her 13th birthday. Before she leaves, trying to hold back tears, Matt says that he always loved her.
  • And after that, Jenna tearfully looks at the house as the wedding music starts playing behind her.