In How to Lose Friends & Alienate People Sidney is a disillusioned journalist with a conflicted fascination with celebrity – and a personality that warns women off as effectively as a foghorn – who has a difficult time moving from an alternative London magazine to an upmarket conservative New York magazine.
On his first night in New York Sidney drives away every women he meets in a bar except the beautiful Bobbie (Charlotte Devaney) who he belatedly discovers is a pre-op transsexual.
When Lawrence, another journalist, steals one of his story ideas Sidney brings him a present – Bobbie performing a lapdance in his office. Unfortunately Sidney hadn’t realised it was bring your kid to work day and just as Bobbie turns around with everything hanging Lawrence’s wife arrives with his two young daughters.
Peter King was the hair & makeup designer. I don’t know who was responsible for Charlottes prosthetic appendage – if anybody can clarify the credits, please email themakeupgallery.