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Getting used to being human was taking its toll on Castiel, and he forgot to sleep and eat more often than not. Dean helped him as much as he could, but he could not look out for him 24/7, even though he would prefer to. He would hate if something happened to Cas, especially now when they were together, and when the former angel had given up his heavenly home and his immortality to be with Dean - something he could never reciprocate. Dean just wanted to do his damned best to make Castiel’s sacrifice worth it. So he did not scold Cas when he forgot to eat, and he did not get angry, when he found him, eyes red-rimmed and peering up from a book, at the ass-crack of dawn. He would simply extend his hand, grab Castiel by the sleeve and drag him to their bedroom. He would mute Cas’ apologies with light, sincere kisses to his lips and forehead, as he carefully took off his clothes piece by piece. Then he would drag him to bed, wrap him up in comforters and blankets, and tangle their limbs together, octopus style, in an attempt to prevent Cas from sleepwalking or getting nightmares. He would weave their fingers together, stroke his hair, and whisper sweet nothingness into his ear, until Cas drifted peacefully off to sleep. Yes, Dean did his best to make sleeping a pleasant experience for Castiel, and in time he would learn, and more often than not be the one to drag Dean of to bed, whispering ‘I love you’ and be the one to tangle their fingers together.