Just a little idea that's been bouncing around my head for a while!
I figured since we got to a point in Boomer's Big Dinner where we've introduced Miles' parents and how ok they seem with their son dating a man, it's fairly obvious that even if Miles never came out to them they've always sort of known.
Between the look of Miles' outfit and the desktop PC, the CRT monitor displaying the Sims 1 loading screen, and the Fellowship of the Ring poster on the back (I've already established Miles really likes LotR several times) it's a very 2001-looking picture.
I know when I first introduced Miles back in 2020 he had 'milesniall84' as his username, which would have made him 35 at the time, but 41 now. I don't think I'm sticking to birth years so closely but I do think it's ok if the characters have aged a bit (I don't want to run into a Simpsons-type situation where, say, Homer would now have been born after the time the first season aired, Jesus Christ someone put that show out of its misery) so if Miles is 37 now that would make him 11 to 12-ish around 2001.
Considering what I usually draw, adjusting to these proportions for preteen Miles was a bit tricky and required some feedback from friends to get right but I think the end result looks alright. Also, I'm thinking Xavier used to have a shorter haircut when Miles was young and long hair was perceived as less appropriotate for men. He only started growing it out later in life as a bit of a flex, since the fact that he's not balding (or the tiger equivalent) in his early 60s means he likely had a stress-free life.