Anna Calthorpe, formerly Lady Anstruther-Gough-Calthorpe, has lost her legal bid to recover £427,000 from her former boyfriend, Stephen Constable-Maxwell. The funds were allegedly spent on rent, luxury holidays, dental work, and recreational equipment during their four-year relationship.

Southampton County Court Judge Glen dismissed Calthorpe's claim in its entirety on August 14. The judge also ordered Calthorpe to pay 80 percent of Constable-Maxwell's legal costs, with an initial payment of £75,000 due by the following Friday. Constable-Maxwell's counterclaim against Calthorpe was also dismissed.

Calthorpe, 51, who has four children, began her relationship with Constable-Maxwell, a 62-year-old former City financier, in 2016, following the dissolution of her marriage to Sir Euan Anstruther-Gough-Calthorpe. Constable-Maxwell moved into Calthorpe's farmhouse in Hartley Wintney in November 2016 and resided there until their relationship ended in August 2020.

Her lawsuit was based on a loan agreement signed in December 2016, initially capped at £50,000 with a 5 percent annual interest rate. Calthorpe contended that this agreement had been expanded to cover all her expenditures on Constable-Maxwell over the subsequent four years, citing WhatsApp messages as acknowledgment of the debt. Her claimed expenses included £160,177.96 for rent, £57,753 for holidays to destinations such as Cuba and the British Virgin Islands, and unspecified amounts for dental work and kite-surfing gear. She also claimed £215,000 put on her credit card for him and an additional £343,595 transferred to his account, minus £273,500 he reportedly paid to her builder.

Constable-Maxwell denied owing any money, asserting that the only binding agreement was the £50,000, which he claimed was fully repaid with a £76,000 payment in 2019. His counterclaim alleged that Calthorpe had assaulted him on multiple occasions, including pulling a knife, repeatedly punching him, breaking his nose twice, and kneeing him in the testicles, which required surgery. His counterclaim also sought £26,460 for counseling and £148,500 for farm work he claimed to have performed.

Neither party was awarded any funds from the other. The dispute began when Calthorpe first issued her demand in March 2021.