Lord Denning (1899-1999) is commonly considered to be the greatest judge in the world, at least within the past couple of centuries. However, he also had a difficult love life

When he was 15, Denning fell in love with the 14-year old daughter of the vicar of his church. However, she only wanted to be friends. For 15 years, he tried to win her love, and when he was 30 and she was 29, she finally fell for him. While he wasn't a judge yet, by the time he earned her love he had fought in WWI, graduated top of his class in math at Oxford, taught Math and Geology at Oxford, became a lawyer, won a legal scholarship, wrote a legal case commentary, and wrote the manual for the Railway police.

Regarding his marriage, he did not have a happy ending as she became ill soon after, causing the couple to spend a lot of time apart, and she died after 11-years of mutual love. https://en.wikipedia.org/wiki/Tom_Denning,_Baron_Denning#Early_life_and_studies