The West Wing
S3E21
· Posse Comitatus

C.J. and Simon Tense Over Boundaries and the NY Trip

In C.J.'s office, Simon discloses he's Anthony's Big Brother for three years, prompting her warm approval. She insists there's no need for him to join the New York trip since she'll travel with the President, attempting to enforce distance post-kiss. Simon invokes Secret Service prohibitions against dating or kissing protectees, teasingly confronting her about their kiss—which she denies—while playfully breaching protocol by using her first name. Reaffirming professional lines, he stubbornly declares he'll board the plane anyway. C.J. watches him exit, their flirtatious tension underscoring fragile personal stakes amid duty's pull.

Plot Beats

The narrative micro-steps within this event

3

Simon and C.J. retreat to her office, where they discuss his role as a Big Brother and the upcoming trip to New York.

professional to personal ["C.J.'s Office"]

C.J. attempts to dissuade Simon from accompanying her to New York, leading to a flirtatious exchange about their previous kiss.

defensive to playful ["C.J.'s Office"]

Simon reaffirms his professional boundaries but insists on accompanying C.J. to New York, leaving her to watch him depart.

frustration to resignation ["C.J.'s Office"]

Who Was There

Characters present in this moment

5
Anthony (Toby Ziegler aide)
primary

Content and expectant, buoyed by earlier banter and impending souvenir

Anthony exits to the lobby at Simon's instruction just prior to the office entry, remaining absent during the private disclosure of their mentorship and flirtatious exchange, yet serving as the emotional pivot for Simon's revelation and referenced in Simon's exit plan to take him home.

Goals in this moment
  • • Await souvenir for mother
  • • Maintain brotherly bond with Simon
Active beliefs
  • • Simon handles threats competently despite teasing
  • • White House ties yield special rewards
Character traits
loyal affectionate
Follow Anthony (Toby …'s journey
C.J. Cregg
primary

warm and approving toward Anthony, tense and assertive with Simon

greets Simon and Anthony, arranges souvenir via Carol, enters office with Simon, insists he skip NY trip, denies kiss, watches him leave

Goals in this moment
  • • enforce professional distance from Simon post-kiss
  • • facilitate souvenir for Anthony
Character traits
resilient strategic poised terse dutiful
Follow C.J. Cregg's journey
Simon Donovan
primary

Playfully defiant with underlying confidence, blending attraction and professional resolve

Simon enters C.J.'s office post-lobby, discloses his Big Brother role with humble pride, initiates flirtatious banter invoking Secret Service rules, teases about their kiss, breaches protocol by using her first name, asserts job seriousness, mentions taking Anthony home, and exits declaring he'll join the New York flight.

Goals in this moment
  • • Advance flirtation while testing professional boundaries
  • • Insist on accompanying C.J. to New York despite prohibitions
Active beliefs
  • • Mutual chemistry overrides strict protocols without real risk
  • • Personal rapport strengthens protective duties
Character traits
playful defiant charming dutiful persistent
Follow Simon Donovan's journey

Location Details

Places and their significance in this event

1
Carol's Desk

C.J.'s office provides a confidential sanctuary immediately after lobby interactions, framing the duo's shift from public warmth to private tension; its enclosed space amplifies whispers of forbidden flirtation, backstory revelation, and rule-bending defiance, heightening intimacy amid the administration's moral and political tempests.

Atmosphere Charged with flirtatious electricity and restrained desire, taut with unspoken attraction
Function Private venue for boundary-testing dialogue and emotional disclosure
Symbolism Embodies the permeable divide between professional duty and personal vulnerability in the White House pressure …
Access Restricted to senior staff and assigned Secret Service, barring casual observers
Doorway as threshold for entry/exit, symbolizing breached barriers Intimate confines fostering hushed, pointed exchanges

Organizations Involved

Institutional presence and influence

1
Big Brothers and Big Sisters of America

Simon explicitly reveals his three-year commitment as Anthony's Big Brother, humanizing his Secret Service stoicism and prompting C.J.'s approving warmth; this personal tie counters the episode's themes of loss and control illusions, injecting mentorship's redemptive light into flirtatious friction.

Representation Via Simon's direct personal testimony as volunteer mentor
Power Dynamics Softens Simon's authoritative agent role, yielding relational influence over C.J.'s perception
Impact Highlights volunteerism as counterweight to political cynicism and personal grief
Foster long-term youth mentorship bonds Inspire replication through positive role modeling Member's lived experience shared in conversation Emotional appeal via familial 'Big Brother' narrative

Narrative Connections

How this event relates to others in the story

What led here 1
Character Continuity medium

"Simon Donovan's protective and flirtatious behavior towards C.J. escalates from playful banter to a more intimate connection."

Simon's Playful Big Brother Banter and C.J.'s Souvenir Gesture
S3E21 · Posse Comitatus
What this causes 1
Character Continuity medium

"Simon Donovan's protective and flirtatious behavior towards C.J. escalates from playful banter to a more intimate connection."

Simon's Playful Big Brother Banter and C.J.'s Souvenir Gesture
S3E21 · Posse Comitatus

Key Dialogue

"SIMON: "I'm not allowed to date a protectee.""
"C.J.: "Who's trying to date you?""
"SIMON: "I'm not allowed to kiss a protectee.""
"C.J.: "Who's trying to kiss you?""
"SIMON: "You did.""
"SIMON: "See you on the plane.""