The 'This Morning' host was channelling her inner Patsy Stone as she was seen quaffing on champagne and puffing on a cigarette outside a West London bar with the reality star.
They then hopped in a taxi to exclusive drinking hole Groucho Club where they continued their evening.
Happily married Holly has revealed she has a 'crush' on Francis, and the pair have met up a few times after striking up a rather random friendship.
And yes, her husband Dan Baldwin knows about it!
Holly Willoughby and Francis Boulle
Holly and Francis were introduced on 'This Morning' when the cast appeared on the show.
She told him: "I have this weird obsession with you! Can we have lunch after the show?"
They eventually met up at Holly's local, tweeting a snap together, with Holly later admitting to Heat magazine that she has 'stalked' the star to get him to come out with her.
She said: "Francis Boulle is my favourite (from 'Made In Chelsea'), I stalked him, got his number, dragged him to my local and everything."
Talk about an unlikely pairing.