Hi anon! I’m having a hard time believing this was totally spontaneous. Even if it seems like it was a last minute thing, this show has to be prepared and organized before hand, so I don’t think he just decided to show up just before the ceremony. I think it was scheduled a minimum. I don’t know if it was his idea or The Webbies’ idea, though.
I’m guessing their team organized the whole thing knowing they’d both be in NY at the same time. I believe they did that behind Gillian’s back, though and she didn’t know. She looked genuinely surprised when he was presenting so it seems to me like she wasn’t prepared to receive her award from him, which makes the whole thing even sweeter!