From left to right: Soren, Dan, Michael, Katie, and Cody from "Cracked After Hours" (And possibly "Today's Topic". The two series seem to take place in the same universe, though Cody would need some explaining)
I always watched the videos without thinking too hard about it and just listening to their stupid pop culture conversations, but then I stumbled over the fandom and it was pointed out that the characters are implied to have almost soap opera level complex relationships (Michael and Katie having slept with each other, Katie moving on to lusting after Soren but Michael ruining it by trying to turn it into a threesome which scared Soren away, Soren and Dan getting closer, and Katie starting to resent Dan for it because it's heavily implied Dan is bisexual too so Katie might be thinking he's succeeding where she failed, despite Soren being straight and them clearly just being friends)
(EDIT: Turns out the real Daniel O'Brien have said the characters Soren and Daniel are in fact "accidentally falling in love" so ignore everything I said about them just being friends)
The picture is based on the Joss Whedon episode where the running joke that Soren, Michael and Katie doesn't seem to care much about their previous conversations is explained by their memories having been wiped by a shady group of people lead by Cody (he works for shadowy people in Today's Topic too, so they might not notice him being everywhere they go thanks to mind meddling). Dan cares more about them than they seem to care about him because he remembers more, which must be a bit of a nightmare for him considering how one of his biggest fears is for them to leave him.
And to make it even darker Michael has been memory wiped so many times he got brain damaged, and he seems to be aware of it on some level. He gets more intelligent when he gets drunk, he obsesses over alien abductions and having experiments done to him, and in Today's Topic he starts crying and admits to feeling empty and thinking of himself as a sleeping princess waiting for a prince to wake him up. He knows he "isn't all there" and want someone to save him from whatever is being done to him. His attempts at Soren could be because Soren is the closest they have to a classic Disney prince/hero, but unfortunately Soren is under the "spell" too, so Michael won't be getting any help from him.
Their biggest hope is Dan who for some reason isn't being memory wiped, but his self esteem is too low to do anything, and ironically they're making his insecurities worse for seeming like they don't care.
Hell yeah, I just overthought After Hours! How the tables have turned! Humon out! *drops chicken leg in soup*