I’d lean towards fool around some and have some sort of a weird pseudo relationship going on that never really culminates into anything serious for either of them. the reasons for that can vary for both foggy and dean, which could have as much to do with dean’s extracurricular activities as it does with his uncertainty regarding his sexuality. I doubt he’s even 100% okay with his sexuality now (hello super heteronormative military). some good ol’ fashioned tension between them while still remaining good friends.

so let’s tentatively say dean’s parents move them to new york when he’s sixteen (he’ll drop out when he’s between 17-18 which I’m sure is a decision that foggy is super excited about). he gets his own super sketchy place in new york for awhile, but eventually his extracurriculars start to interfere with his ability to hold even a sketchy, under the table part time job, and maybe somewhere between 19-20 he lives with foggy for awhile. until foggy’s like “okay, listen, you gotta actually do something with your life buddy, wasted potential, yadda yadda, and dean decides around 20 that his only real viable option is the military at this point. how does that sound? (please feel free to alter anything or add any input to the timeline, foggy is yours after all.)