Will's Awkward Oval Debut and Toby's Soft Landing
Plot Beats
The narrative micro-steps within this event
Will arrives expecting to meet Toby but learns Toby has been called to the Hill by Leo, creating immediate uncertainty.
President Bartlet unexpectedly invites Will into the Oval Office, leading to an awkward interaction where Will struggles with proper address and purpose.
Will attempts to recover from his blunder with Charlie, who offers half-hearted reassurance about his performance with the President.
Toby returns and ribs Will about his 'Presidential flameout', but sets up another meeting with Bartlet, showing belief in Will's potential.
Who Was There
Characters present in this moment
Neutral, focused on logistics and access, unobtrusively supportive.
Affirms Toby's request to arrange a few minutes with the President this evening, providing the scheduling authority Toby needs to convert the awkward interaction into a formal meeting.
- • Schedule a brief presidential meeting for Toby and Will
- • Keep the President's evening schedule organized
- • Staff must facilitate access when senior staff request it
- • Orderly process prevents chaos in presidential scheduling
Not directly emotional; functions as institutional reminder of outside politics.
Mentioned indirectly through campaign posters observed in Toby's old office windows; Sam's campaign is a contextual background presence rather than an active participant in the encounter.
- • Maintain electoral visibility (symbolically represented)
- • Signal continuing political activity outside the White House
- • Campaigning appears everywhere; lines between campaign and office are constantly policed
- • Visual presence can influence staff commentary
Teasing and pragmatic on the surface; quietly protective and authoritative, shifting the embarrassment into mentorship.
Returns from the Hill, teases Will about the 'presidential flameout,' arranges a later meeting with the President via Bonnie, offers blunt paternal advice about handling loneliness and the urge to drink, and directs logistics for the evening.
- • Shield and mentor Will after an awkward encounter
- • Secure a formal opportunity for Will to meet the President
- • Maintain communications team's professionalism and schedule
- • Embarrassment can be reframed as a learning opportunity
- • Senior staff must guide junior staff through career hazards
- • Direct, honest counsel is preferable to platitudes
Unremarkable, businesslike; performing expected clerical duties without fanfare.
Offers Toby a plain piece of paper (scheduling information), handing it to him as part of routine staff support; a brief, transactional action that enables Toby's scheduling of the follow-up meeting.
- • Deliver scheduling information to Toby
- • Keep communications office workflow moving
- • Small logistical gestures keep White House operations functioning
- • Timely delivery of information prevents scheduling errors
Calm and practiced; slightly amused but sympathetic toward Will's discomfort.
Greets Will in the Outer Oval, explains Toby's absence, introduces Will to the President, offers a weak attempt at reassurance after Will's embarrassment, and watches the interaction with quiet, protective professionalism.
- • Facilitate presidential access while keeping visitors comfortable
- • Protect the President's schedule
- • Defuse Will's embarrassment
- • The President's time must be protected but visitors deserve courtesy
- • A little humor can diffuse awkwardness
- • Junior staff will survive their first humiliations
Distracted but efficient; performing routine tasks while larger interactions proceed.
Alerts Toby that Lisa Lily at the Justice Department is on the phone asking for the date of Albert Anastasia's death; takes Toby's response and thanks him, keeping White House communications running amid interpersonal business.
- • Provide accurate information to external callers
- • Keep internal staff informed of outside inquiries
- • External agencies expect quick, precise answers from White House staff
- • Administrative duties continue even during personal moments
Amused and personable while remaining in control and focused on substantive business (the Congressional notes).
Casually opens the Oval, asks if Toby has arrived, recognizes Will, invites him in, references having sent notes on the Congressional section and gently redirects the meeting logistics, then returns to the Oval when excused.
- • Ensure staff are briefed on the Congressional section
- • Maintain accessibility to staff without derailing schedule
- • Gauge the competence of people working on White House communications
- • Face-to-face interaction is valuable for clarity
- • Substantive work (the Congressional section) is the priority
- • Staff should not be intimidated by the office of the Presidency
Composed and neutral; a stabilizing, domestic presence in the communications space.
Sits in Toby's office and answers his question about Albert Anastasia's death date without fanfare, then is left to wait while Toby and staff handle the evening's scheduling—a quiet, matter-of-fact presence that humanizes Toby.
- • Wait respectfully for Toby while he finishes work
- • Provide factual answers when asked
- • Family interactions can be simple and direct even in strange places
- • Answering a question honestly is sufficient
Off-screen urgency; expecting accurate, quick answers for a departmental event.
Referenced as an external caller (Lisa Lily of the Justice Department) seeking the date of Albert Anastasia's death—her request triggers a factual exchange but she is not physically present in the event.
- • Obtain historical date for a Justice Department event
- • Rely on White House contacts to provide detail
- • External agencies depend on White House staff for logistical help
- • Small details matter for official departmental functions
Objects Involved
Significant items in this scene
The 'notes on the Congressional section' are referenced by President Bartlet when he suggests they prompted Will's visit; they are the substantive reason the President assumes Will is there, framing the misunderstanding that causes Will's embarrassment.
A staffer hands Toby a plain piece of paper containing scheduling information; this small document supplies the 7:30 appointment time Toby tells Will, enabling the conversion of Will's humiliation into a concrete follow-up.
Toby jokingly suggests 'plain oak tag' as the appropriate material for covering campaign posters in federal buildings, using the object as a rhetorical prop to scold staff and restore professional decorum in his old office.
Shaving cream is invoked by Toby as a humorous, regulation-friendly alternative to overt campaign materials—again a rhetorical device that diffuses tension and underscores his wry managerial style.
The Oval Office window exists in the scene as part of the Oval's threshold when Will is ushered in; while not directly touched, it frames the Presidential space and underscores the institutional gravity Will experiences on entering.
Location Details
Places and their significance in this event
The Communications Office functions as the immediate follow-through space after the Oval encounter; Toby and Will move there to debrief. It is the workplace where Toby transitions from teasing to mentorship and where staff logistics (scheduling, posters, phone calls) continue amid personal moments.
Sam's West Wing Office stands in for Will's office (the private space Toby enters to confirm the 7:30 time). It is used for the private, paternal exchange in which Toby gives Will direct counsel about coping and drinking—turning public embarrassment into private mentorship.
Capitol Hill is invoked as the reason Toby was initially unavailable—Leo needed him there—establishing competing institutional demands that precipitate the encounter and underline the show's larger stakes between executive and legislative priorities.
Organizations Involved
Institutional presence and influence
Sam's Congressional Campaign appears as a visual and contextual presence (posters in Toby's old office windows), prompting Toby's comment about laws against campaigning in federal buildings and signaling the porous border between campaign activity and White House space.
The U.S. Congress is the substantive backdrop: Bartlet references 'notes on the Congressional section' and Toby was summoned to the Hill. Congress's existence shapes staff priorities and creates the scheduling friction that produces Will's ill-timed Oval encounter.
Narrative Connections
How this event relates to others in the story
"Julie's precise knowledge of Anastasia's death foreshadows his later attempt to explain his criminal past to Toby, deepening their familial tension."
"Julie's precise knowledge of Anastasia's death foreshadows his later attempt to explain his criminal past to Toby, deepening their familial tension."
"Will's awkward first meeting with Bartlet sets up his later passionate defense of campaign finance reform, showing his growth under pressure."
"Will's awkward first meeting with Bartlet sets up his later passionate defense of campaign finance reform, showing his growth under pressure."
"Will's awkward first meeting with Bartlet sets up his later passionate defense of campaign finance reform, showing his growth under pressure."
"Will's awkward first meeting with Bartlet sets up his later passionate defense of campaign finance reform, showing his growth under pressure."
Key Dialogue
"BARTLET: Want to come in?"
"WILL: Oh, no, no. No, no, no."
"TOBY: Listen, when you get home tonight you're going to be confronted by the instinct to drink alone. Trust that instinct. Manage the pain. Don't try to be a hero."