Of all the Bond Girls, Moneypenny was always my favorite. Long-suffering, administratively excellent, frumpy, pragmatic, saucy and salty Moneypenny. You could depend on her to be in her seat, doing her job, making the world safer for 00 agents everywhere (and everyone else by proxy), and you could depend on her to flirt shamelessly with James Bond. And in full knowledge of the flirtation’s futility.
Dr. No (1962)
Miss Moneypenny: James! Where have you been? I’ve been searching all over London for you.
[Picks up phone]
Miss Moneypenny: 007 is here sir.
[Slaps Bond’s hand away from the papers on her desk]
James Bond: Moneypenny! What gives?
Miss Moneypenny: Me, given an ounce of encouragement. You’ve never taken me to dinner looking like this. You’ve never taken me to dinner…
James Bond: I would, you know. Only “M” would have me court-martialed for… illegal use of government property.
Miss Moneypenny: Flattery will get you nowhere – but don’t stop trying.
Lois Maxwell, who originated the character, was not an unattractive woman. Take a look at her and Honor Blackman, the notoriously well-bedded-by-Bond Pussy Galore, side-by-side from Goldfinger:
Not a lot of difference there, but miles of difference in how Bond related to them.
I could always relate to Moneypenny. I wasn’t ever going to be the girl James Bond went out of his way to wrangle. I would be the one fetching his coffee and bantering back at him. It would be okay and friendly because we would both know, though he would be kind about it, that he had absolutely no interest in me (or even recollection of me) once he’d hung his hat and passed by my desk into M’s office, leaving me to daydream over what it might be like to be fancied by the world’s most dangerous spy. Would I have tapped that given the chance? Absolutely not. I’m smarter than that. And that’s why Bond never would have really given Moneypenny a go. She was too smart for that.
What I didn’t get as a child was that it was no negative reflection on me that James Bond would have passed me by. It was all on Bond himself. Aside from his likely fear of rejection from someone he obviously respected, Bond was too damaged to manage a relationship. There was always the whisper that Moneypenny was too smart, too professional, and too important for Bond to bring into the vortex of his romantic life. He didn’t worry about destroying cars, watches, or anything else Q gave him, but you know that Bond would never have intentionally hurt Miss Moneypenny. Misuse of government property is right.
If Moneypenny had been some little dink secretary, do you really think he’d have given a go a second thought? He bagged less attractive babes. But Moneypenny was a smart woman with a tongue as sharp as his, and a wit to challenge his best one-liners. She was one of the only other characters who ever got to give Bond as good as he gave her.
This is why I am so disappointed with the new Moneypenny, who took a desk job because she wasn’t good enough to be in the field. Real Moneypenny had her job because she earned it–you don’t get to that level chewing gum and missing shots. Real Moneypenny could match Bond’s wit. As gorgeous as Naomie Harris is, and she is STUNNING, I will always prefer Lois Maxwell’s guns.
Also, Bond respected Real Moneypenny enough to know her name.
Goldfinger (1964)
James Bond: What do you know about gold, Moneypenny?
Miss Moneypenny: Oh, the only gold I know about is the kind you wear… you know, on the third finger of your left hand?
James Bond: Well, one of these days we really must look into that.
Miss Moneypenny: How about tonight? You’ll come over for dinner…
[playfully tosses Bond’s hat onto the hat rack]
Miss Moneypenny: and I’ll cook you a wonderful angel cake.
James Bond: Well, nothing would give me greater pleasure, but I’m afraid I have a… business appointment.
Miss Moneypenny: [laughing] That’s the flimsiest excuse you’ve ever given me. Oh, well, some girls have all the luck. Who is she, James?
M: [over intercom] “She” is me, Miss Moneypenny. And kindly omit the customary byplay with 007. He’s dining with me and I don’t want him to be late.
Miss Moneypenny: [to Bond] Then there’s hope for me yet.
James Bond: [gives Moneypenny a playful peck on the cheek] Moneypenny, won’t you ever believe me?
The Outside Lane 