I load up their open world games and fast travel them to a random discovered town.
If they pick it back up recently, they'll wonder why the hell they're in Ravenhold when they were last in Whiterun. If they don't pick it up soon then it doesn't matter anyways as they'll have no idea where they left off.
If you really want to fuck with him, cook him a nice dinner, get some romantic candle light, and throw down some rose petals, and wear that lingerie he really likes, and lie down sexily in his bed.
Do things that are nice, but werid.
Like, make his bed, but upside down. Turn the welcome mat around, after you take it out and beat off the dust. Put away laundry but turn all the hangers backwards.
Run out and get some frozen shrimp. Duct tape two or three at a time to the undersides of his furniture. Poke a few small holes in each piece of tape so that the eventual aroma can permiate.
If they pick it back up recently, they'll wonder why the hell they're in Ravenhold when they were last in Whiterun. If they don't pick it up soon then it doesn't matter anyways as they'll have no idea where they left off.
Like, make his bed, but upside down. Turn the welcome mat around, after you take it out and beat off the dust. Put away laundry but turn all the hangers backwards.