To be honest, if it were me, I’d ditch the Escher-esque drawing. As B said, it doesn’t sit well with the type
In a way, it is a fairly expected way of illustrating ‘unexpected’. Again, as B said, I’d make it just typographic and do something actually unexpected with the word, ‘unexpected’. Melt it, explode it, give it antlers, etc – obviously keeping it legible, whilst pushing that legibility to the extreme, you’ll get away with it as it’s for teenagers.
To my mind, the whole thing needs to be a lot edgier and 'yoof’ culture. Maybe look at graffiti tags and doing one in Baskerville, et al - dunno, just thinking out loud.
Perhaps flip the whole idea and rather than taking something sane and expected and making it unexpected, Take something anarchic and make it predictable. Not sure what. I am just spewing, hopefully to give you other avenues to explore.
To my mind, if you are dealing with kids – especially at-risk ones – you need to speak their language if you are going to get anywhere near getting them to engage with mainstream ‘conservative’ (as they will likely see it) culture. Have you got access to these kids? Speak to them. See what their influences are. What music they are listening to (ergo, album covers they are looking at), etc.
You’ve probably been through all these thought processes a thousand times already, but, if I’m being honest, the whole thing feels a bit like talking to kids using what ‘grown-ups’ think is ‘down with the kids’ phrases whilst wearing a baseball cap backwards.
Kids see through that sort of stuff straight away. At best, they may see it as patronising, at worst they will find it risible. Either way, they’d be unlikely to engage. That age group – especially if they aren’t on a fast track to the ivy-league – are very culture-savvy and extremely nuanced. You need to speak their language,
Apologies if it is not what you want to hear. Hope it helps in some small way.