47. Keanu Reeves and Alexandra Grant

Keanu Reeves, one of the A-list bachelors of Hollywood, has, to a huge degree, dated a long list of celebrity women in the past. However, he never got married and has yet to succeed in making his romances turn into marriage.

In the past couple of years, it seemed like The Matrix superstar has taken a different path and started dating women who are not in his line of work and at par with his age. He started dating Alexandra Grant in 2018, a visual artist who specialized in painting, sculpture, videos, and other forms of media. Not only did Grant and Reeves form a romantic partnership, but they are also in business with each other. Together, the two put investments in a publishing company. They met in 2011 when they started working together for a book entitled Ode to Happiness and they’ve since become inseparable.