The holidays are almost here, which means you might soon be awkwardly interacting with multiple generations of your family under one roof. So what's the key to bridging the generation gap? On this Now or Never, meet people going outside their comfort zone to try and connect with people much older — or younger — than themselves. A Toronto comedian asks her dad, the king of dad jokes, to perform stand-up with her — and has an eye-opening moment with him on stage. A millennial finds a creative way to bridge the generation gap in her workplace. And a grunge-loving musician creates an unexpected musical mash-up with his grandpa, the unofficial polka king of southern Manitoba.