S4:E14 “Last time I checked the intern packet, I don’t think “pimp daddy” was included in the description of duties.” – Other intern
So Blair was back at W magazine and everything’s great except for the fact her supervisor, Epperly, was giving her crap for not being able to do 10 things in an hour. To Blair’s credit, she knew she was more capable than completing a checklist, so when Epperly found herself in a crisis to find a venue for Florence + The Machine to perform, Blair offered her assistance. Epperly shot her down by telling her to stick to making sure the post-it notes were dripping in her fuchsia-tights-under-shorts-in-winter saliva was dripping all over the office post-its instead. Suddenly, Blair realized that in addition to finding a venue for Epperly and proving her capabilities that way, she was going to solidify a great performance review by getting her supervisor laid. So Blair brought Epperly to Chuck’s apartment and convinced him to lend them The Palace for the magazine’s event. She also introduced Epperly to Nate, who dutifully whisked her upstairs to check out the view from the roof and virtually out of the episode entirely. While alone, Chuck and Blair realized they both needed each other’s help for the first time in a long while (or at least since “Love The Way You Lie” was a new song in the real world).
In order to try and keep his father’s company from being driven into the ground by Mr. Thorpe, Chuck spent the previous three days having sex with Raina, Mr. Thorpe’s daughter, in hopes that her attachment to Chuck would make her convince her father not to ruin his father’s work. But his days in bed with Raina weren’t affecting her perpetual meeting attendance in amethyst at all. So when Chuck and Blair were alone together, he asked why his efforts to make Raina fall for him weren’t working, and Blair said that instead of sleeping with her all day he should spend some time trying to form a connection with her, by perhaps bonding over an activity that’s mutually enjoyed. Blair asked if Chuck would consider helping her in alleviating all of Epperly’s tension before her performance review was submitted, but Chuck said he was too zonked out from being with Raina. So obviously, who was next in line for the role? None other than Nate, whose dead relationship with his convict father has left him with no agenda of his own and two inches from starting an Upper East Side plant planting business.