Leo Macdonald is having a bad day. He's lost his job (this isn't the first time he's been sacked) and then ends up playing gooseberry on a night out with his brother James. Things start to look up though when he falls into conversation with his neighbour at the bar. Leo is immediately attracted to this beguiling older woman, Judy, and asks her out on a date. Leo's mother, Pam, is furious when she learns that her boy is going out to dinner with a 'much older' woman. But Leo doesn't care, he knows that he's just met someone very special.

Leo and Judy are looking forward to a low-key Sunday lunch at the Nelson. Their plans are thwarted though when Leo's family turn up at the pub and hijack their date. This awkward situation is then exacerbated by the arrival of Judy's mum Peggy and her sister Jackie. And then there's Geoff, an old friend of Judy's who's very confused as he hasn't seen her since she transitioned. Judy shares her story with Geoff and, as the day progresses, begins to feel that maybe she should come clean with the Macdonald clan too. But is this really a good idea? As Jackie says, "It could go seriously Jeremy Kyle!".

Leo and Judy go to see a new exhibition at the art gallery. They were expecting watercolours but end up viewing some provocative and surprising photographs instead - which prompt Leo to quiz Judy about what exactly was involved when she transitioned. And, more importantly, whether she is still able to have sex! Later, they go bowling and have a great time until two lads start querying Judy's gender and generally trying to cause trouble. Judy tells Leo to ignore them but the lads test her patience to the limit. Meanwhile, Peggy and Jackie pop in to visit Pam at the hair salon and decide to make a day of it.

Tonight's the night! Judy and Leo plan to spend their first night together as Tony and Pam are going away and Leo has conspired to get James out of the house too. Romance soon drops off the agenda though as Leo loses his nerve when confronted with hard evidence of Judy's former life. Judy is devastated by his change of heart and the evening ends disastrously. When Pam and Tony return from their trip they find a very depressed Leo who tells them that his relationship is over. But, following a tender heart to heart with his Dad, Leo realises that he really does love Judy and he goes to find her to try and make amends. Meanwhile, James puts his talent for mimicry to good use.

Geoff has promised to give Leo a try-out as a salesman at his car showroom. Tony is ill, but Pam is unsympathetic and leaves him in James's care. Having coerced Leo into agreeing that she can use his family's house for Judy's surprise party, Peggy arrives at the Macdonalds' 'to see what she's working with' and, hearing that Tony is unwell, appoints herself as chief nurse. James discovers that Tony has been reading up about transsexuals and assumes this means that his dad is gearing up to transition himself. When he discovers the truth he heads off to talk it all through with Judy. Meanwhile, Leo is repelled by Geoff's creepy and inappropriate interest in Judy - and ends up walking away from the job. Pam comes home to an unwelcome surprise.

It is Judy's fortieth birthday and the day of the not very surprise party. Leo wants to buy her a really lovely present but is strapped for cash. Party preparations are afoot at the Macdonald household and Pam's not happy about the gaudy makeover of her home - but that's nothing compared to how she feels when she learns the truth about Judy - and discovers that she is the last family member to be told. Leo proposes to Judy, but she assumes he is joking and turns him down. He puts on a brave face but is broken-hearted. While the party gets underway, Pam goes round to the Arkley house to have a very difficult conversation with Judy: "I've hit a woman before, oh yes! And don't think I wouldn't lay one on a transsexual!" Is this the end of the road for Leo and Judy?