Look at what happens when someone tries too hard to get down with the kids.
The poor old New Zealand police service embarrassed itself on Monday by sending a tweet that made light of having to tell someone their relative had died.
The message on the official police Twitter read: "When we have to tell someone their family member has died in a crash" and was illustrated with an image from TV comedy series The Office with the lead character saying: "This is the worst."
It was a shocker, which was quickly deleted and followed up by an apology.
"They were trying to do the right thing and connect in a different way and quickly realised within two minutes they had completely misjudged the tone and the imagery," a police spokesman said.
Since the emergence of youth culture, stuffy institutions and companies have been trying their best to tap into it in order to sell things, to engage or to appear relevant.
During the recent election we saw endless examples of politicians trying to play the cool mum or dad, whether it was Bill English's awkward walk/run video, social media posts of karaoke on campaign buses or selfies at brunch.
Hillary Clinton's attempt at it famously backfired during last years' US election when university students slammed her for tweeting: "How does your student loan debt make you feel? Tell us in 3 emojis or less."
In one tweet she lost the very people she was trying to engage.
Mostly these examples are no more than cringeworthy, but when it goes wrong it does more harm than good.
The thing about the language of youth culture is it's only really understood by those who have created it.
Culture changes constantly but authenticity will always connect.