James Bond: His 5 Most Promising Relationships (& His 5 Worst)

James Bond has been paired with a lot of women, and even saying “a lot” is putting it very mildly. There’s an entire list where the women are segregated according to chronology, film, and designation as either love interest or femme fatale. Suffice it to say, this guy’s had a lot of relationships.

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There were a certain few we think he had a special connection with and who could be seen as continuing as his love interest; there are also those girls who could never be with him for a number of factors, mainly because most wanted to kill him. In this list, by “promising”, we mean the ladies that had further potential to be with him, which eliminates Bond’s wife straightaway. So, read on below to see which women were promising and the ones most ill-fated for him.

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Vesper Lynd's death scene from 'Casino Royale'
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10 Worst: Vesper Lynd (Casino Royale)

Vesper Lynd's death scene from 'Casino Royale'

Many consider Vesper as the ultimate love for James, as these two were most definitely in love – something that’s remarkable for Bond. However, it was easily destructive due to the fact that she was a double agent for Quantum and her betrayal of Bond led to her death.

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Before her passing, his love for her prompted Bond to resign altogether from his role as a secret agent and run away with her. Because of Vesper’s influence, Bond had let go of his livelihood, and he didn’t even realize the girl was never his to begin with. The relationship ended in the death of Vesper and the death of Bond’s spirit.

9 Promising: Octopussy

These two started out at odds with one another, as Octopussy was a smuggler and was being built up as the antagonist of the movie. However, things would turn around and they would become lovers, then allies. As far as chemistry is concerned, Bond had loads of this with the character, and they even seemed to have what one might call “puppy love”.

It helped that they were on different sides at the start, as it made for a kind of 'opposites attract' situation. By the film’s end, they reflected the freshness of a new relationship where one is confident things will work out. Her attitude also seemed promiscuous like Bond’s, so they were quite alike.

8 Worst: Severine (Skyfall)

You can’t call a relationship with someone successful if it resulted in their deaths, can you? And Bond’s association with Severine is especially bizarre if you view it on paper. All in all, he approached her to question her about Silva, and then somehow managed in becoming her brief lover.

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The next time we see them together, Silva has figured out Severine’s betrayal, and attempts to get Bond to kill; Silva then executes her himself when Bond intentionally misses. There was no room for growth between these two, not when Bond basically used her for his own ends and was rather cold when viewing her death.

7 Promising: Eve Moneypenny (Skyfall)

Naomie Harris as Moneypenny in Skyfall

In the same film as Severine, we got Eve Moneypenny as well. Moneypenny’s role in Skyfall was unlike any other in previous iterations of the character, as it was Bond doing the chasing rather than her hopelessly pining after him. This was a fantastic swerve from the norm, since it made Moneypenny a prize worth acquiring.

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We don’t know if she ever did become more than just an associate of Bond, but the two continued having a connection in Spectre as well. Some believe that Moneypenny might just end up being the one for Bond in this continuity of the series, due to the potential they have as a couple.

6 Worst: Elektra King (The World Is Not Enough)

Elektra King The World Is Not Enough

There was something definitely there between James and Elektra throughout The World is Not Enough, be it chemistry or underlying feelings. It’s a shame that she turned out to be a nutcase who was really in love with the antagonist, as this lands her in the “worst” pile.

Again, you can’t call their relationship promising in any way, not when he was the one doing the killing this time. Bond did feel for her, as he was visibly distraught for having to kill her; when she brought up he’d miss her too much, that was her mistake. Because James Bond never misses.

5 Promising: Madeleine Swann (Spectre)

All things point toward Madeleine biting the dust like Bond’s wife in the previous chronology, once Bond 25 rolls out, but for the time being, we can consider this coupling a success. Bond not only vanquished all of the Quantum business he’d been dealing with for a decade because of Madeleine, he finally found a woman with whom he could retire.

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They also had an excellent rapport with one another, having been able to beat several villains that came their way as they formed a battle couple of sorts. This relationship holds a lot of promise for the future, although her death is the most likely thing that will kick off the next film.

4 Worst: Miranda Frost (Die Another Day)

Another love interest for Bond, another one who attempted to kill him after betraying him. We’re starting to think James might not have had the best choice in women, as Miranda Frost became the latest lover who fooled him into trusting her.

While their status as romantic partners never carried the emotional weight as Bond had with some other women in this list, he did put his confidence in Miranda. It turned out she was the one responsible for Bond being incarcerated for over a year, and then planned to foil the good guys’ plans until she was killed by Jinx. This one’s disaster level might be the highest due to the lengthy months of torture Bond had to suffer because of her.

3 Promising: Natalya Simonova (GoldenEye)

Almost exclusively, the women Bond has enchanted have a status of being femme fatales, or are very active physically even before they met him; Natalya was always the Plain Jane type of lady, and this made her dynamic with James all the more interesting.

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It was clear she was way in over her head with the conflict she was in the middle of, and the story with Bond felt like an exciting romance on the run. It was nice to see Bond paired with a woman who wasn’t too comfortable among all the guns and shooting; she did everything on the fly, and Bond was attracted to her for it. Unfortunately, it appears as if the secret agent lifestyle was just too much for her.

2 Worst: Strawberry Fields (Quantum of Solace)

We hardly knew ye, Strawberry. But from what we can make of her, she died a brave person. Her characterization onscreen was basically being all talk about not falling for James’ charms, before she inevitably did just that and fell into bed with him.

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However, just before her death, she did accomplish in warning Bond that the villains were coming for him, making her more than just an ex-lover. Still, as far as her relationship with James is considered, we’d be willing to wager Strawberry would’ve preferred never meeting him rather than being subjected to such an awful death like getting dunked in crude oil. Calling this death a “disaster” is more than appropriate here.

1 Promising: Jinx (Die Another Day)

If you think about it, the first chronology of James Bond ended with this couple having been made official. Using that logic, we can conclude that this version of Bond finally found the woman for him in Jinx. There could be no better either, as Jinx was pretty much Bond in female form.

She was fast, dangerous, quick witted, and maybe even more experienced in prowess than Bond. They didn’t need the other to stay safe, and just enjoyed each other’s company as equals. Since there will never be a sequel to this timeline, Jinx and Bond can be considered together forever.

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