Continuity: Anytime during Seasons One or Two. (Pre Casino Night.)
It's funny because he really sees her upside down.
Pam, the shy, quiet, receptionist.
Pam, the most ordinary, dull girl one could find.
Pam, the meek young woman with no goals in life.
Pam, the girl trapped in a loveless, never-ending engagement.
Pam, the definition of settling.
He doesn't see her in any of those ways. He knows better. His best friend, the girl he's desperately in love with, well, she doesn't match any of those statements.
The woman he loves is talented and creative and wants to pursue her passion for art more than anything else on the world.
The woman he loves can make him laugh until tears spill out of the corners of his eyes, whether it is by helping him pulling pranks on Dwight, or by simply sharing a look of shock or annoyance whenever Michael speaks.
The woman he loves is beautiful, so incredibly beautiful to him, that he thinks a new word should be invented, only to describe her beauty. None of the already existent words seem enough for him to convey it.
The woman he loves is caring, loving, compassionate, and she has the biggest heart among all the people he's ever met.
The woman he loves is the best friend he could possibly ask for – even when she might accidentally break his heart from time to time. It doesn't matter. He knows it's probably his fault for falling for her in the first place.
The woman he loves, with all her little dreams of art classes and a good husband who'll love her and a house with a terrace she can put flowers in, is, to him, the definition of being wonderful.
The woman he loves is flawless, and sometimes he thinks he's not worthy of her.
Yeah, it's as if he sees her upside down.
Every little thing people don't notice about her - he knows it by heart.
And every little thing she doesn't like about herself - he loves it dearly.
But he also sees her upside down in another way, when he imagines her in a situation that's different from her current life – when he pictures her being happy, and getting everything she ever wanted, and finding someone who loved her exactly the way she was.
Someone like himself.
Whenever he pictures his life with Pam – the dating period, the proposal, the engagement, the wedding, then kids… - he feels that he needs that desperately, as if losing the possibility of having that future might be his death sentence. He wants to have that so bad… he simply can't help by day-dreaming of it. Without those little fantasies he is sure he would not make it through the day.
Of course, seeing her the way he does has downsides.
Because despite how great it is to think of the happiness that can be achieved, but every time he sees the engagement ring on her finger, he is reminded of reality. He remembers she's not his, but someone else's, and that she will get married soon – that's when the little that's left of his hope fades away and suddenly he doesn't care much about life anymore – he knows he'll just keep on existing, but living like a normal person is impossible without her.
If only he could stop seeing her upside down.
Even better: if only reality could stop reminding him that he sees her upside down.