Bobbi Hepburn (formerly Robert) is the pre-operative transgender sister of Mimi Maguire who visited the Chatsworth Estate during Series 8. Though Mimi always spoke fondly of her brother who worked in Show Business and who she'd not been able to contact, she revealed her true feelings when Micky tracked Bobbi down. Bobbi was nearing the end of her gender reasignment surgery at the time of her visit in Series 8, waiting for the vaginoplasty alone.
Bobbi caused quite a splash with the Chatsworth residents and the Maguire Family, when she arrived and revealed her new gender. It was revealed that though Mimi always spoke fondly of her brother she had in fact hidden when he'd tried to visit and thrown away his letters, too ashamed and unwilling to accept her brother's burden.
Micky locked the siblings in The Jockey's cellar to sort out their differences, which they did. The siblings even went so far as to book into Micky's talent show at The Jockey, singing a duet. But Micky soon began to worry when he noticed Bobbi was insulting Mimi behind her back, using her for free drinks and because she had nowhere else to go, Micky confronted his aunt over her behavior only to be told that she doesn't care and she knows he would never break his mother's heart by revealing all.
Later, when using the toilet in The Jockey Micky noticed something sticking out of the back of a toilet. He lifted the lid and discovered a plastic bag containing a large wad of cash, The Jockey's takings, only for Bobbi to walk into the cubicle behind him. Bobbi tried to suggest they split the money, go on a sunny holiday together, all the while looking more and more nervous, promising Micky that his family will never respect him. Already angry with Bobbi over the insults she'd happily spread about his mother, Micky called for Jamie and Shane.
Confronting her sister Mimi was genuinely hurt by her actions. Bobbi explained that while Mimi often said she never got the brother she wanted, Bobbi never got the sister she wanted either. The siblings continued to argue over their upbringing, how they'd each been embarrassed by the other's entire persona and appearance. Mimi then asked how much it would cost to complete Bobbi's gender reasignment, to while she replied "priceless", Mimi handed back the stolen takings and said a last farewell to her sister.
- The young niece of Mimi, Ruby Hepburn arrived on the estate during Series 9. Due to her familial ties and shared last name it can be assumed, though it hasn't been mentioned, that Ruby and Bobbi and closely related.
- In the commentary for Episode 511 it is mentioned that some scrapped story ideas for that episode included Paddy Maguire being one of triplets, with the third brother being a transsexual and Mimi's brother arriving. These scrapped ideas seemingly combined into Bobbi.