In the first of three editions, he embarks on a road trip with fellow comedian Matt Forde to uncover different attitudes to relationships. They start off by meeting a couple who have been married for 54 years to see if they can provide answers. The boys then encounter people who contest the norm when it comes to co-habiting and marriage, such as swingers, and receive an invitation to the wedding of a couple who have six marriages between them. Jon also arranges for Matt to visit one of the UK's leading matchmakers, which leads to two dates in one night

The award-winning comedian gets to grips with mortgages, marriage and parenthood as he and his friend Matt Forde examine people's relationship with cash - does it buy happiness and if so, how much does an individual need to be contented? Jon has always had an uneasy relationship with money. Having grown up with his mother and sister not owning their own home, by his twenties he was driven to succeed as a stand-up and buy his own property. Jon and Matt visit a lottery winner whose windfall proved to be a blessing and a curse, discuss the effect of inherited wealth after encountering a billionaire's children, and meet the man who elected to give away his millions and move from a stately home to a two-bed flat.

On the final leg of his road trip, the comedian explores parenthood, asking whether he has what it takes to be a good father. He and Matt Forde meet a couple who have been through several cycles of IVF and have invited them to experience the birth of their child. They also talk to a 'Dink' - a dual-income couple with no kids - and are put to the test looking after a virtual baby and a toddler football team. Jon is also paired up with a seven-year-old for a survival course - can he build a shelter or simply hang out with a youngster for a day?