This Time Around (2003) Timeline Explained – Every Event in Order

Drew and his popular friend group played a cruel prank on Melissa. After finding her missing notebook filled with doodles of their names, they left a fake note in her locker supposedly from Drew, asking her to meet him at lunch to be asked out. When Melissa approached Drew hopefully, the group publicly revealed it was a joke to humiliate her in front of the entire school cafeteria.

Foreshadowing: Earlier scenes show Melissa's innocent crush and the circulating notebook that eventually reached the wrong hands.

• drew hesler
• junior high prank
• melissa humiliation
• popular kids bullying

Melissa still carried deep-rooted trust issues from the junior high humiliation. When her friend Gabby suggested using the restaurant project as an opportunity to make Drew fall in love and then break his heart, Melissa saw it as a chance to finally get closure on the past trauma by turning the tables on Drew.

Foreshadowing: The opening flashback establishes how deeply the humiliation affected Melissa, leaving lasting emotional scars.

• melissa revenge
• gabby plan
• getting even
• past trauma

Drew revealed to Melissa during their date that he had just ended a decade-long relationship with Cara Cabot, the popular girl from their old school. He explained he was ready to move forward and start fresh, suggesting he had outgrown the relationship and wanted something different.

Foreshadowing: Cara's appearance during the date hints at the recent breakup and her desperation to win Drew back.

• drew breakup
• cara cabot
• long term relationship
• moving on

When Cara's mother learned rumors about Melissa's junior high identity as "Pissy Missy," she warned Cara that Melissa might be more trouble than she's worth. This childhood nickname, likely derived from Melissa's name, was used to shame her and became part of Cara's attempt to drive a wedge between Melissa and Drew.

Foreshadowing: The junior high humiliation planted the seeds for this later weaponized nickname.

• pissy missy
• childhood nickname
• cara's mother
• rumor

As Melissa spent more time with Drew following the revenge plan, she discovered he had genuinely changed since junior high. During their date at the restaurant, Drew shared vulnerable details about his financial risks and recent breakup, showing honesty and growth. His willingness to acknowledge past mistakes and his sincere interest in Melissa gradually broke down her defenses.

Foreshadowing: The date scene marks the turning point where professional chemistry starts becoming personal.

• genuine connection
• drew changed
• vulnerability
• trust building

Gabby realized their revenge scheme had gone too far and was causing more harm than good to both Melissa and Drew. When Cara and her allies revealed the ruse to Drew, Gabby recognized her mistake and joined forces with Cara to try to push Drew away, though Drew insisted he wasn't the same person from junior high.

Foreshadowing: Gabby's growing discomfort throughout the plan foreshadows her change of heart.

• gabby guilt
• cara alliance
• scheme exposed
• redemption

When Cara confronted Drew with the junior-high nickname "Pissy Missy" to drive him away, Drew felt guilt about his past actions. He went to Melissa's apartment to talk things through, acknowledging that his behavior in junior high was childish and demonstrating his commitment to not repeating those mistakes.

Foreshadowing: Drew's guilt was building ever since he recognized Melissa's identity at the restaurant.

• drew guilt
• apartment visit
• confronting past
• making amends

Several factors contributed to Melissa's decision: Drew's genuine apology and acknowledgment of his past behavior, his demonstrated growth as a person, and Gabby's invitation urging Melissa to attend the grand opening. Melissa chose to separate her past hurt from present feelings, allowing herself to see Drew for who he had become rather than who he was in junior high.

Foreshadowing: Gabby's phone call inviting Melissa to the opening represents the shift from revenge to reconciliation.

• forgiveness
• moving on
• second chance
• personal growth

During their date, Drew explained to Melissa that the restaurant venture was funded entirely from his own money. If the restaurant failed, he would be financially ruined. This vulnerability showed Melissa a different side of Drew, one willing to risk everything for a new start.

Foreshadowing: The financial stakes add tension to the grand opening and raise the emotional stakes for Drew.

• restaurant funding
• financial risk
• drew investment
• new beginning

Cara arrived at the restaurant during Melissa and Drew's date to beg Drew to reconsider their ten-year relationship. Even though Drew had already broken up with her, she wasn't ready to let go and tried to win him back, creating tension and uncertainty in the budding romance.

Foreshadowing: Cara's desperation hints at her later attempts to sabotage Melissa's reputation.

• cara interruption
• jealous ex
• relationship tension
• dating