It’s safe to say that if this particular mash-up happened, one of the two shows wouldn’t have aured for very long. Four seasons and counting with no word on Ted’s wife to be. Not in Chuck and Blair’s universe.
Dorota would clearly have been dispatched, stat, to do some digging.
But suspending that particular aspect of doubt for a second, how would Lily and Ted etc go down with the Gossip Girls. They’re all in Manhattan, which would help. The age difference might be a problem, but given that all the actors look the same age anyway, I think we could get over that.
Both shows are essentially about relationships, and there could be plenty of potential romances and bromances blossoming there.
Nate and Marshall could bond over ‘eating sandwiches’ together, Ted and Dan over being dumped by blondes who were way out of their leagues.
Barney and Chuck make strange bedfellows, but can you imagine the classic dialogue if the pair were to go on a night out together. They’d paint the town, they would.
Suits, suave, a splash on insincerity; Legendary,
And of course, Barney would try it on with all the Gossip Girls, but only Serena would be stupid enough to fall for his “It’s my last day on the planet” routine. Vanessa would probably punch him.
Blair would much prefer Robyn and Lily than any of the guys. Lily has excellent scheming ability; with Blair’s tuition she could certainly be the next Queen L of Maclarens. And Robyn? Always wears the trousers in her relationships, something Blair would definitely be on board with.
But in general, not a match made in heaven. Gossip Girl is all about glamour, luxury, class. The odd-bods on HIMYM just don’t have good enough credentials. They hang out in the same bar every night, their idea of fun is an ongoing slapping contest. Only Vanessa would be OK with that, and that’s only because she’d be being ‘ironic’.
They have jobs, and not acceptable ones either – Ted is a prof proffess professor (how do you spell that!) and Robyn presents a really bad early morning news show. Lily works with children.
To Blair, she’s basically Dorota.