this isn't like an AU or anything but I think it'd be funny if Desmond worked at one of those bars that played popular shows and recorded their entire bar reacting to them. Game of Thrones was a popular one for this when it was playing. and it'd be funny to have Desmond have that "half paying attention mostly doing his job" kind of knowledge of popular shows. (and also imagine if that was how he was first noticed by Abstergo he'd be so mad he doesn't really use youtube and he didn't know the bar was recording it) (or he does know they record and instead he wears a mask during those events and gets a weird following online of people looking for him during the reaction videos like an active where's waldo)
This would work since Desmond would be still working in Bad Weather when Season 1 (2011) and 2 (2012) first aired.
Customers and regulars would first notice him because he doesn’t seemed to know a lot of tv shows or even movies but he likes to listen to people talk about them.
He’s also quite handsome and a lot of people like to comment that he could be an actor if he wanted to (or a model if he doesn’t know how to act)
Desmond just laughs it off, unable to tell them that, considering he’s hiding his past to everyone, he’s pretty much acting as the normal dude Derek Miller for years now.
He’s happy with his life and there’s no way in hell that he would jeopardize it by plastering his face all over those screens by becoming an actor and getting his father’s ‘cult’ on his tail.
He did realize that a lot of people liked to take pictures and videos when he’s working (especially when they’re playing the newest episode) but Desmond has had a lot of practice of dodging cameras as it was part of the training on the Farm (“Remember, Desmond, the Templars is always watching”)
This causes people to talk about the hot bartender that is so hard to get in photos and videos. It becomes like a game to the regulars because they honestly believe Desmond isn’t doing this on purpose.
Then, during the 2nd season’s final episode (because it just became so much popular), the bar decided to make all the employees wear costumes and everyone decided that Desmond just feels like he would do well as Jon Snow.
Desmond agreed because he didn’t really mind but he realized that he fucked up when everyone wants to take a picture of him because (1) he does rock the Jon Snow outfit and (2) he’s hot.
The fact that his father’s cult or the supposed evil megacorporation didn’t come bursting through his doors afterwards gave Desmond the courage to try for a motorcycle license.
And the rest, as they call it, is history.