What I would do, is give him a more classic middle name (in terms of English fashions, if that's where you live).
I would definitely not be giving him Alan, Derek or Darren (or Wayne, Dean, Gary or Barry) as a mn, as altogether, that would sound like some weird 80s (named in the late 60s or 70s) tribute name. Like sticking a mullet on a baby. (Alan, Derek and Graham are more late 50s / early 60s, so kids of the 70s names).
There is something about the Sharon, Tracy, Donna, Dean, Wayne, Darren and, to some people's minds, Kev, era, that really sticks in people's minds, along with Essex Girls, white stilettos and Viz magazine. That social moment somehow transcends the normal background level of class prejudice. But, those of us whose minds it sticks in are mid-40s and older now, so older than your DS's school-friends' parents.