@the denial of holding of the Mafia bois: that sound like quitter talk, and i am quite strong and NOT a quitter.
(( Hmmm.... I really like your vibe there, so I’ll add two more headcanons just for you~ ))
Mafiatale Sans: Should you succeed in lifting him, you will absolutely catch the skeleton off guard. He’ll just kind of lay in your arms for a moment, looking at you in surprise... before absolutely lighting up. He’ll wrap his arms around your neck and make some half flirt/half joke about you carrying him away into the sunset. Anytime you pick him up after that will bring out the most genuine laugh and some serious quality time between the two of you. Probably the best method of getting him away from his work and onto the couch to cuddle.
Mafiafell Sans: He won’t be exactly surprised, as it takes a very determined sort to be around Don, but deep down you will earn a special little bit of respect from picking him up like that. He really likes the moxie it takes, so expect the flirting/teasing to increase tenfold while he’s in your arms. Secretly, he loves being held, it gives him a very good excuse to ignore thr responsibilities of a mob boss in favor of playing Casanova with his favorite human.











