Lewis Milestone was a fine director, who did many fine films in his lifetime -- but as this movie demonstrates more than adequately, comedy (especially frothy romantic comedy) did not suit him. Charles Winninger is the best thing in My Life With Caroline, though everyone tries hard, to little avail -- Ronald Colman is Ronald Colman, so no one paying money to see this film was going to feel cheated on that level. But what should have been a clever, bright romantic romp instead seems leaden in key spots and often just plain annoying elsewhere, with Anna Lee, in particular, seemingly in over her head portraying a character who is supposed to be flighty in the cute way but comes off as obnoxious. My Life With Caroline was a major RKO production in its time, but it's easy to see why it never carried much of a reputation, and it is definitely not a "lost" classic waiting to be re-discovered, despite a seemingly stellar cast.