Theakston married Sophie Siegle in Ditchling on 15 September 2007, and they live in west London. They have two children. He was previously romantically linked to socialite Lady Victoria Hervey, actor Joely Richardson, and models Erin O'Connor and Sophie Dahl. He is a keen fencer and competed for Sussex in 1985. As captain of Ditchling Cricket Club, Theakston was a member of the first cricket team from England to play the Afghan cricket team in Kabul. He is a member of Mensa and a supporter of Brighton & Hove Albion. Theakston took a break in 2003 to travel to Uganda to meet with former child soldiers. He is a patron for CANCERVIVE – a charity established to address the needs of anyone whose family or friends are cancer sufferers. He played in his fifth successive Soccer Aid match at Old Trafford in June 2014. Having, in 2010, saved four penalties for England against the Rest of the World in a penalty shoot-out, before missing a penalty himself in a defeat, he was later named man of the match for his performance in goal. On 4 October 2019, Theakston took an 8 day break from Heart Breakfast to set off on his Bike Britain Challenge, a cycling event for Global's charity Make Some Noise. The event lasted 8 days, with Theakston cycling 650 miles from Edinburgh and arriving in London on the 11th. Along the way, he stopped at Newcastle upon Tyne, Leeds, Manchester, Birmingham, Cardiff and Bristol, and met numerous life threatened children and their families.