I’m not sure if Hook realizes how much Henry will be around when they are back in SB and that Emma would probably never leave him there to go off adventuring or something like that without him. Emma’s life has completely changed now because of Henry.
His previous involvement with a mother of an adolescent was leaps and bounds different than his current predicament. Milah ran away from her problems and put her child behind her lover in her priorities. They may have wanted to go back for Bae, but they never did. Fast forward and we have Emma, who is only now connecting with the son she gave up. A reversal. He’s going to be clear and present in her life and she’s no longer going to let him be sidelined into the background. Whoever she ends up with has to realize and accept this.
Keeper of Rumplestiltskin's and Neal's spears and war paint and crystal ball.