Love's Greatest Mistake is a 1927 American silent drama film directed by A. Edward Sutherland and starring Evelyn Brent. The film is now lost.

Philandering husband George Montfort purchases railroad tickets for a weekend tryst in the mountains with his latest paramour. When his wife Yvonne finds the tickets, George hastily explains that they were bought as an anniversary present for her. Yvonne doesn't believe George, but she decides to use her ticket anyway, while George remains behind in Paris on "business."

Playboy Teddy Ward wants to marry Jeannie King, an artist, but his father wants him to marry Loris Lane, but tells Teddy he can marry whom he pleases if he will make the Mountain Inn a profitable operation. Teddy agrees, and with the support of his friends arranges an ice-boat race with a $10,000 prize to the winner. A problem arises when his father refuses to pay such an amount. Teddy thinks one of his friends will win the race and refuse the prize, but champion racer "Duke" Slade shows up and Teddy knows he will take the money. Some movie stars show up and, while using their own names, are definitely not playing "Self" in this fictional film.