The Complex Relationship Between James Bond and Miss Moneypenny

The Evolution of Miss Moneypenny

James Bond's relationship with women is one of the most complex and essential aspects of his character, but his connection to one woman in particular has always remained somewhat enigmatic. Appearing in 23 movies since her debut in 1962's Dr. No, Miss Moneypenny is an MI6 stalwart, pivotal in both Ian Fleming's novels and the movies they subsequently inspired. However, for all her ubiquity, Moneypenny's relationship with Bond is relatively mysterious.

Ian Fleming with Daniel Craig as James Bond

For the first 14 films in the James Bond franchise, Moneypenny was played by the same actor. Lois Maxwell defined the character throughout the Connery, Lazenby, and Moore eras, providing a subtly sympathetic and occasionally flirtatious foil to Bond's debonair ego. After Maxwell retired, the role was filled by Caroline Bliss, who played the part in both Dalton installments. Samantha Bond and Naomie Harris followed, each bringing a new interpretation and energy to the part. However, throughout each iteration, questions around Moneypenny persist – particularly over whether she and 007 were ever romantically involved.

James Bond kisses Miss Moneypenny in Die Another Day.

Despite all four versions of the character having a very intimate relationship with Bond, 007 and Moneypenny do not sleep together during any of the James Bond movies. In fact, a key feature of Moneypenny's character, certainly through the earlier Bond films, is that she is one of the few women with whom he has a platonic relationship. Despite some films using outdated stereotypes, Bond and Moneypenny are friendly with a flirtatious edge, rather than anything more explicitly amorous.

James Bond with Miss Moneypenny in Goldfinger.

The Unconsummated Connection

Although the two characters are never shown sleeping together on-screen, there is plenty of evidence that the relationship is more than a simple friendship. For instance, Lois Maxwell is seen weeping at Bond's wedding in On Her Majesty's Secret Service. Meanwhile, Samantha Bond's take on the character was simultaneously repulsed by and attracted to Brosnan's super spy. In The World Is Not Enough, she reacts with jealousy when Dr. Molly Warmflash sleeps with Bond. She even imagines herself in a similar situation in Die Another Day, only to realize that her fantasy is a holographic projection. Scenes like this suggest a complexity between the pair, even if the feeling is never consummated.

James Bond with Miss Moneypenny in You Only Live Twice.

One of the films that best explores the romantic side of Moneypenny and Bond's relationship is Skyfall. Not only does she accidentally shoot Bond in the film's opening scene, but she is then seen suggestively shaving him in his hotel room. Given the circumstances and Bond's track record, the situation seems perfectly set up for the two characters to sleep together. However, despite the romantic energy, the characters do not actually sleep together. This has been confirmed by none other than Moneypenny actor Naomie Harris herself. In an interview with Cinemablend, Harris hypothesized: 'People always ask me if they slept together. I don’t think they did. I think Moneypenny and Bond can’t ever cross that line because they’re both so professional. There’s definitely something that’s been bubbling underneath but the question is, ‘Will it bubble over?''

Skyfall Naomie Harris as Eve Moneypenny Sniper Cold Open

Bond and Moneypenny in Literature

Much like the James Bond films, Ian Fleming's books depict a platonic relationship between the pair. Part of the reason for this is that Moneypenny's role is very different in the literary source material. For one thing, Bond actually has his own secretary who fulfills the role that Moneypenny does in many of the movies. In some cases, this can create the sort of complications some viewers have anticipated from Moneypenny's characterization in the movies.

James Bond with Miss Moneypenny in Skyfall.

For instance, in the novel The Man With The Golden Gun, one of Bond's former secretaries (Mary Goodnight) actually becomes the story's main love interest. By contrast, Moneypenny is generally a more peripheral figure, who may harbor unrequited feelings for Bond, but never lets her professionalism falter. Although the Moneypenny seen in the movies is more of a composite of Bond's literary secretaries, it's telling that neither the books nor the James Bond films have decided to change the core dynamics of their relationship.

James Bond with Miss Moneypenny in Tomorrow Never Dies.