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It's not a good day for Big Bob. After avoiding Iona all week, he finally plucks up the courage to tell her he's a virgin and she laughs in his face. From there on he just can't escape talk about sex and sexual experience, making him feel even more inferior. While Annie's party is in full swing, Jimmy finds Bob moping at home. Jimmy misconstrues the reason for Bob's glum mood and convinces him to go to the party, reminding him that Scarlett's illness has taught them to live each day to the fullest. Bob arrives at the party but is immediately embarrassed by yet more chat about sex and a comment from Deek about Iona's promiscuity. Bob jumps on the chance to evict a warring Robbie and Jack from the party then doesn't go back.

Weighed down by his feelings of inferiority, and desperate to get his first time out of the way, Bob seeks out a prostitute. But, just like the rest of his day, it all goes horribly wrong. The prostitute turns out to be a police officer and Bob is arrested for soliciting. Back at the party, Iona continues to try and reach Bob to apologise. She leaves him a message, only having the courage to say 'I love you' after she has hung up.

The next morning Jimmy presumes Bob spent the night with Iona, he is horrified when Bob confesses the truth. Bob is mortified but clinging to the fact that at least no one else will find out. Little does he know that the local newspaper is carrying a front page spread of his arrest and minxy Nicole is out to broadcast the gossip to greater Shieldinch. When Bob turns up for work he is immediately confronted by Murray and the paper. Bob's thoughts instantly turn to Iona and he quits his job just to get away and see her. But Molly gets to Bob first. She is quick to give him a flea in his ear but is ultimately sympathetic. When Bob finally reaches Iona he's too late. He makes an emotional plea for forgiveness during which he tells Iona he loves her. She tells him to leave.

Things are awkward between Jack and Hayley as he returns to work at the salon. Jack wants to clear the air but Hayley is behaving oddly. She tells Jack and Robbie to take the rest of the day off and as soon as they leave she empties the till's takings and heads out. Meanwhile, the Military Police turn up at the Brodie house. Coincidence? As Jack and Robbie get stuck into the fizz at Iona's, Hayley meets her secret rendezvous in a dodgy part of town. It's Leo. He tells her he's gone AWOL and she gives him the money from the salon to keep himself going.

Jack and Robbie make a show of themselves by getting into a drunken scuffle at the party. Big Bob kicks them out and they realise they've been out of order. They make up over Gordon's secret whisky stash and Jack confesses he never meant to hurt Hayley. Robbie says he knows. The next morning they wake up in No18 with stinking hangovers. Robbie convinces Jack to go round and clear things up with Hayley - and get some clean clothes. Jack lets himself into Hayley's flat to find a raging Hayley who practically throws him back out. As soon as Jack is gone we discover the reason for her overreaction - Leo spent the night. Leo then feigns a happy phone call to the family for Hayley's benefit and after a few awkward moments, they kiss.