This Time Around (2003) Characters, Setting & Themes Explained

The film shifts between two main time periods. The past scenes take place in junior high and Catholic high school, while the present-day story unfolds in Melissa's public relations firm and Drew's restaurant. These contrasting settings highlight how childhood experiences echo into adult life.

• setting
• locations
• junior high
• restaurant
• office

The movie uses a two-period timeline. It begins with Melissa in 8th grade, then jumps forward about eleven years to present day where she works as a successful PR executive. This time gap shows how childhood experiences shape adult choices and relationships.

• time period
• present day
• flashbacks
• junior high

The film explores three interconnected themes: Revenge, as Melissa and Gabby plan to use romance to break Drew's heart; Growth, showing Melissa's transformation from humiliated student to confident executive; and Forgiveness, as both characters confront their past and work toward reconciliation.

• themes
• revenge
• growth
• forgiveness
• redemption

Melissa Rochester is a successful PR executive who still guards her heart after being humiliated by Drew in junior high. She uses strategic thinking and wit to navigate work and romance, but secretly craves genuine connection. Her character arc involves learning to trust again after past hurt.

• melissa
• pr executive
• main character

Drew Hesler is the once-popular boy from junior high who now owns a restaurant. He carries guilt about harassing Melissa in middle school and presents himself as changed. His past actions complicate the trust and romance in the present day, forcing him to prove his genuine desire to make amends.

• drew
• restaurant owner
• character background

Forgiveness is central to the reconciliation between Melissa and Drew. Drew's guilt over past cruelty and willingness to change becomes a testing ground for trust. The path to mending their relationship requires honesty, accountability, and becoming different from who they were in junior high. The ending reinforces that forgiveness can reset relationships.

• forgiveness
• trust
• reconciliation
• redemption

Revenge serves as the initial driving force when Melissa and Gabby plan to use Drew's affections to break his heart, mistaking revenge for empowerment. This scheme exposes the fragility of trust and the cost of manipulating someone's feelings. The consequences become a catalyst for self-reflection and ultimately lead Melissa toward genuine growth.

• revenge
• scheme
• manipulation
• consequences

The contrasting settings emphasize the story's emotional journey. Junior high represents where trust was broken, while the modern PR office and restaurant symbolize where healing occurs. The Catholic high school memories frame rivalries that resurface later, creating a full-circle narrative about confronting the past.

• settings
• junior high
• restaurant
• symbolism

Gabby Castellani is Melissa's best friend who becomes an ally in the revenge plot, orchestrating increasingly elaborate schemes at first. She underestimates the harm she causes until she witnesses the consequences for both Melissa and Drew, ultimately supporting Melissa's journey toward forgiveness.

• gabby
• best friend
• supporting character

Melissa's transformation from a humiliated junior high student to a confident adult executive is the film's emotional core. The romance tests her boundaries, teaching her to balance ambition with vulnerability. Small developments in maturing boundaries, better communication, and resilience after social humiliation ultimately reframe old hurts as lessons.

• growth
• transformation
• character arc
• maturity