This is a typical modern comedy starring Douglas Fairbanks, before he began on his path of adventure swashbucklers with "The Mark of Zorro" in 1920. Some of them, such as "Wild and Woolly" (1917), are quite good. "Flirting with Fate", however, is lacking. As fellow commenter wmorrow59 said, the pacing is slow to begin, especially when compared to a film like "Wild and Woolly". It's much too tiresome for a comedy.
The pacing does pick up after Fairbanks's deal with Automatic Joe, though. Finally, Fairbanks employs his acrobatic skill for humor. Hiring an assassin to kill oneself is always a promising plot device, and the resulting irony this time had me chuckling. Giving a receipt for the business transaction is hilarious. On the other hand, the comical intertitles in the style of Anita Loos lack her cleverness. Sometimes they address the audience--or the orchestra, but they seem forced. Loos had worked with Fairbanks on "His Picture in the Papers", "The Mystery of the Leaping Fish", and, later, "Wild and Woolly", giving him his voice. This film could have used her and her husband director John Emerson.
The pacing does pick up after Fairbanks's deal with Automatic Joe, though. Finally, Fairbanks employs his acrobatic skill for humor. Hiring an assassin to kill oneself is always a promising plot device, and the resulting irony this time had me chuckling. Giving a receipt for the business transaction is hilarious. On the other hand, the comical intertitles in the style of Anita Loos lack her cleverness. Sometimes they address the audience--or the orchestra, but they seem forced. Loos had worked with Fairbanks on "His Picture in the Papers", "The Mystery of the Leaping Fish", and, later, "Wild and Woolly", giving him his voice. This film could have used her and her husband director John Emerson.