Matthew is the third son of landowner and entrepreneur David Matthews from his second marriage to Rhodesian-born Jane Spencer Parker, an artist. His mother was educated at the Slade School of Art. He is named for his maternal grandfather, Robert Spencer Parker, an architect. He has an older half-sister, Nina, and two older brothers James and Michael.
The family owned Caunton Manor, a 30-acre estate in Nottinghamshire, and Eden Rock in Saint Barthélemy, one of the top 100 resorts in the world. Matthews split his childhood between the two residences. He was educated at Eton. In 1999, when Matthews was 10 years old, his brother Michael was killed in a mountaineering accident on Everest, hours after becoming the youngest Briton to conquer the peak.
He attended the University of Southern California where he studied cinema and television with the aim of becoming an artist but he left after nine months. In 2007, upon purchasing a 10,000-acre estate with hunting lodge in Scotland, his parents acquired the Scottish courtesy titles of Laird and LadyGlen Affric.
Matthews worked as a public relations manager, actor and as a foreign exchange trader at Icap currency brokers. He came into the public eye through the E4 constructed reality show Made in Chelsea. His storylines have tended to focus around his love life, with the first series beginning with his friendship with Caggie Dunlop supposedly leading to something more. He has gone on to date several cast members, earning him a reputation as a Lothario. Matthews reportedly has left the show after media coverage of a supposed steroid drug problem.
In 2012, Matthews was the principal participant in The Bachelor UK series 5. In 2015, he participated in the fifteenth series of I’m a Celebrity…Get Me Out of Here!, but withdrew after two days. In 2013, Matthews wrote his auto-biography, Confessions of a Chelsea Boy. On 12 March 2017, Matthews won the fourth series of the Channel 4 reality series The Jump.
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