Ashley Grant (played by Jodi Lyn O'Keefe) is a protagonist in Whatever It Takes.
Ashley is the school's most popular girl and Chris's cousin. Ryan initially pursues her as his dream date, following Chris's advice to act dismissively to gain her attention. She attends the prom with Ryan, but he eventually leaves to find Maggie after realizing Ashley is not the right person for him. Ryan Woodman (played by Shane West) is a protagonist in Whatever It Takes.
Ryan is a socially awkward geek who wants to date Ashley, while remaining neighbors and best friends with Maggie. He makes a deal with Chris to help each other romantically, but his deception and changed behavior hurt Maggie. He ultimately confesses his feelings, apologizes, and begins a relationship with her. Maggie Carter (played by Marla Sokoloff) appears in Whatever It Takes.
Maggie is Ryan's cute, intellectual neighbor and best friend, while Chris pursues her through their romantic bargain. She is misled into believing Chris wrote the love letters and becomes hurt by Ryan's dishonesty. After exposing Chris's plan at the prom afterparty, she accepts Ryan's apology and realizes they love each other. Chris Campbell (played by James Franco) appears in Whatever It Takes.
Chris is a football jock and Ashley's cousin who wants Maggie. He offers Ryan a romantic exchange, using Ryan's heartfelt letters while advising him about Ashley. Although he attracts Maggie, Chris plans to abandon her after sex, so she humiliates and leaves him restrained at the prom afterparty.
Whatever It Takes (2000) character relationship network mapped with AI analysis. Explore the connections, alliances, and conflicts between characters.
Characters
Ashley Grant
(played by Jodi Lyn O'Keefe) — protagonist
Ashley is the school's most popular girl and Chris's cousin. Ryan initially pursues her as his dream date, following Chris's advice to act dismissively to gain her attention. She attends the prom with...
Ryan Woodman
(played by Shane West) — protagonist
Ryan is a socially awkward geek who wants to date Ashley, while remaining neighbors and best friends with Maggie. He makes a deal with Chris to help each other romantically, but his deception and chan...
Maggie Carter
(played by Marla Sokoloff) — supporting
Maggie is Ryan's cute, intellectual neighbor and best friend, while Chris pursues her through their romantic bargain. She is misled into believing Chris wrote the love letters and becomes hurt by Ryan...
Chris Campbell
(played by James Franco) — supporting
Chris is a football jock and Ashley's cousin who wants Maggie. He offers Ryan a romantic exchange, using Ryan's heartfelt letters while advising him about Ashley. Although he attracts Maggie, Chris pl...
Canonical Relationships
Family, romantic, and professional connections based on plot evidence.
Maggie Carter → Chris Campbell
(Romantic Pursuer)
Chris has his eyes on Maggie and asks Ryan to help him win her over.
Ryan Woodman → Ashley Grant
(Romantic Unrequited Crush)
Ryan has eyes for Ashley, the school's most popular girl, and initially seeks Chris's help to woo her.
Chris Campbell → Ashley Grant
(Family Cousin)
Chris is explicitly described as Ashley's cousin.
Story Dynamics
Alliances, conflicts, and narrative interactions that evolve throughout the story.
Ryan Woodman → Chris Campbell
(Deal-Based Alliance)
Chris offers to help Ryan woo Ashley if Ryan helps him with Maggie, and they agree to the arrangement.
Ryan Woodman → Maggie Carter
(Social Best Friend)
Maggie is described as Ryan's neighbor and best friend.
Story Analysis
Two deceptive romantic bargains force Ryan and Maggie to recognize that genuine belonging and love matter more than popularity or manipulation.
Plot Progression
Four Hearts in Orbit
The Dating Exchange
Feelings Change Direction
Letters and Betrayal
The Honest Choice
Directed by David Raynr
Whatever It Takes (2000) · 5.8/10 · comedy, drama, romance
