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The Saddest Moments In TV History, Ranked

#24: Jim Tells Pam He Loves Her On 'The Office'
Jim and Pam are one of those couples who can't get their timing right, and the whole series was spent rooting for them to get together. So when Jim confesses his love to her during the office's casino night, it was both elating and shattering at the same time.

Jim was about to leave the office branch for Stamford, so he confessed his feelings for her, even though he knew she was still engaged to Roy.

"I'm really sorry if that's weird for you to hear, but I need you to hear it. Probably not good timing, I know that, just — "

"What are you doing? What do you expect me to say to that?"

"I just needed you to know. Once."