‘We’re not officially together!’ The Apprentice’s Courtney Wood takes to Twitter after ‘girlfriend’ Jessica Cunningham gets jealous about Calum Best and Chloe Ferry’s flirting on CBB And despite neither of them winning the show overall, Courtney Wood and current Celebrity Big Brother housemate Jessica Cunningham ended up forming their own partnership. It was revealed before Christmas that the pair had begun dating, jetting off for a winter break in the sun together over the holiday season.