Hiya!!!

a “squid” is a slang term for riders who don’t wear proper safety gear and are generally reckless with their riding (squid stands for stupidly quick underdressed and imminently dead). so saying i think dean would squid (or be a squid) is to say i think he would ride in his regular jeans and possibly a leather jacket, but not proper riding gear.

a Fat Boy is a model of harley davidson motorcycle, first released in 1990. they’re a cruiser style, and based on dean’s love of classic american cars (and general rugged white guy style) i think he would be a classic harley guy. (if not a harley, then maybe a honda goldwing from the 80s)

the “german brain bucket” comment was harkening back to the “squid” comment. oftentimes you’ll see (usually older) guys riding cruiser style motorcycles with helmets that only cover their head, and no part of their face (called half helmets). this is the minimum safety required by law in the US (if your state has a helmet law), but they’re almost useless in the event of an actual crash since they have a tendency come right off of your head and do nothing to protect your face (which is often the first thing to hit the ground). people who wear them usually choose them for comfort since they’re much lighter than a 3/4 face (what you’ll commonly see motorcycle cops wear) or full face (think moto gp) helmet, m (although i’ve heard people describe their reasoning as not wanting to be alive if a crash physically disables them). the goofiest looking brain buckets i’ve seen around are the ones modeled after WWI/WWII german military helmets.

i do think dean would wear riding boots, though. i seem to remember him wearing riding boots in the early seasons of the show...

 Every morning when I wake up, Dean is inside the crib, arms wrapped around baby Sam. Like he’s trying to protect him from whatever is out there in the night.

shhhhhhh don't disturb him he is shifting into depeche mode