At the age of seventeen, he was discovered by Albert Mondego who was looking for a young boy for “The Count of Monte Cristo”. After that, he has done many films and at the age of twenty, he was getting lead roles in many movies and television series. In 2008, he won Emmy awards and got the title of 'Most Dashing Duke' by the Entertainment Weekly.

In 2011, he got engaged with Ellen Whitaker. Their relationship did not work for a longer period and they ended up their affair with mutual consent, after a year. In 2012, he started dating actress Gina Carano but still, they do not have any plans of marriage. He is very ambitious person and always thought of living life on peaceful node. He has three wishes in his life; first one, is to live a content life with his family, second one is to have a wonderful marriage and the last one is to be successful and happy person.

Henry’s girlfriend Gina Carano is also an actress, pursuing her movie career. Carano has appeared in movies such as "Fast and Furious 6" and "In the Blood." This career move makes her closer to what Cavill does, as he is also quite busy filming blockbusters.  Despite having blip in their relationship, they are still together. After knowing about Henry’s relationship with Kaley Cuoco, Gina took him back. The set back of having an extra marital affair did not have a lot of impact on their relationship and also in-spite of this relation, their relationship went through many ups and downs. Apart of having so many ups and down in their relationship, this couple is dating each other from several years. Even though they are in a relationship since many years, marriage is not on the cards. While shooting for the Man of Steel sequel in Chicago, Gina was also spotted there with the Henry. Not only this, they have also spotted at many places in the recent times like Vertigo Sky Lounge and the SushiSamba in the city. They seem to be very open about their affair but still avoid discussing their relationship publicly.

Recently, Henry and Gina adopted a puppy together. After spotting so many times together now also with a puppy, it seems they are planning to get married. According to reports, it may be a publicity stunt. There are many rumors about their engagement also, but nobody knows the truth a. Henry always refuses to talk about his personal life.