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First scenario:
Pretty much the above? Hawks could slip into Endeavor's office everyday and troll the man, slapping his ass like above and the like, until one day Enji has enough and confronts Keigo about why the fuck he does it.
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Second scenario:
Every morning, like really early, Hawks goes out of his way to go on a run with Endeavor (uninvited of course). The pair some how manage to develop a bond through this, and it leads to something more!
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Scenario 3:
Enji is feeling bad about being left out (he understands why of course, he's just a lonely old man) and Hawks decides to try cheering him up by offering that he joins him for Christmas photos of their own.
Imjustawreck here sorry it took so long I had to drive