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Really? 22-24 is normal? Have seasons always been so short? I don't remember this being the case even five years ago, but you're probably right. It just seems like summer break is so long and then there are all these other really long breaks too.
Besides the fact that the writers want to draw it out longer? Dunno I mean he's come close so many times, but he always lets something stop him, usually fear or pride. I love Chuck but if he were real I don't know if I could handle him the way Blair does. That's to me what makes them so epic and fun to watch though. In real life I'd have to walk away by now. I dated someone once who had a real problem saying it without a great reason and I couldn't deal with the drama of that personally.
It's funny you mention Grey's because the last episode really excited me again too. I hate the breaks too but it seems like a CW thing maybe because OTH is also gone for awhile. I think their shows must not have as long of a run as the major networks. Maybe because of money?
I don't know what you ship specifically, but Isabelle (who is now on hiatus thanks to Vuck) has I think some of the best fanfic out there. Her stories are really true to character for Chair and the best part is there is quite a few of them. She's on livejournal and at fanfiction.net.