Then, in The Office’s season 2 finale, “Casino Night,” Jim finally confesses his love to Pam, which is followed by an impassioned kiss at his desk. Since Pam remains engaged to Roy, the moment is largely forgotten. Gleeful that she wasn’t embarrassed by her prolonged engagement again, the heavily-intoxicated Pam takes her Dundie and gives Jim an unexpected peck on the lips. However, Michael surprisingly gives her the “Whitest Shoes” award instead. While it isn’t until The Office’s season 3 finale that the pair finally go on a date, their romantic subplot was intensified by two key kisses in season 2.In The Office’s season 2 premiere, “The Dundies,” Pam gets exceedingly drunk at Chili’s when believing she’ll win the “Longest Engagement” award at the office event. Pam begins the series engaged to Roy, while Jim spends The Office season 1 quietly pining over her and hoping she’ll leave her long-time boyfriend. Part of why Jim and Pam have been established as one of the greatest modern TV couples is their compelling will-they-won’t-they dynamic in The Office’s first three seasons. Much debate has been had around whether Jim and Pam’s first kiss was in The Office’s episode “The Dundies” or “Casino Night,” with the context of the latter making it the couple’s real first kiss.
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