Last year he was spotted cosying up to Nigel Farage during a boat trip for two.
Now he's swung full circle on the political spectrum and is trying to entice a rather more left-wing companion.
Joey Essex has been propositioning Jeremy Corbyn of all people - if the leader of the opposition's tweets are anything to go by.
The TV star turned up at an EU rally in Bristol, and managed to snag some one-on-one time with Corbyn, where they chatted about a whole range of issues.
The Labour leader is sometimes criticised for looking a tad scruffy, but this could be a thing of the past after he said he might take some fashion advice from his on fleek companion.
It is a strange marriage of minds, but could it perhaps work?