Leon Scott Kennedy's Relationships
Leon's known relationships in the Resident Evil universe. All the ones I felt like writing about, anyway...
Claire Redfield
Claire is the first human Leon encounters in Raccoon City. He saves her life in the game intro (I'd say establishing him as the real Hero of Resident Evil 2?) and stays in contact with Claire with a radio walkie talkie until the game's conclusion. Leon was frustrated that Claire, who is a sweet girl but fiercly independent, wouldn't listen to his advice whenever he offered it. "Inexplicably" he trusts this young lady's abilities- you know this because he lets her wander the police station and the highly dangerous sewers on her own, while by comparison he doesn't want Ada Wong to leave his side.
We never get enough Claire and Leon interaction to really understand their relationship. But we can tell that the two trust each other and hold each other's abilities in high regard. They seem to work effectively together as a team. Although there's not one tiny bit of a hint of the two having a romantic relationship (Sorry, Claire x Leon fans) it's a pity they don't get to interact again in another video game. Maybe in the future...
Ada Wong
Leon's most important relationship is the one he forged with Ada Wong in Resident Evil 2. With Leon being naive and Ada being cold, calculating, and secretive, they made an odd couple. But sometimes, opposites attract. Leon's unwavering innocence and dedication to justice warmed Ada's heart and made her feel emotions she hadn't felt in a long time, so we can deduce by how she attempts to articulate her feelings in Resident Evil 2.
Ada: I know I'm not capable of caring about anyone but, I don't want to lose you.
Perhaps Leon inspires her to bring out the good in herself that she once abandoned. Maybe she dreams of abandoning her position in the Grey area and running away to make a decent life with Leon on the "good" side. Or maybe she thinks he's really hot and she just wants to fuck him. Either way, we know Ada is attracted to Leon and dedicated to using her abilities to protect him.
Leon still has feelings for Ada in Resident Evil 4, although he is skeptical of her motives and cynical when he interacts with her in the game. He might not be madly in love with Ada, but Leon tells us his own feelings about Ada at the end of Resident Evil 4, "She's a part of my life I just can't let go of, let's leave it at that."
Annette Birkins
By the time Leon meets Annette, she's aggressive and emotionally unstable. Leon is one of the few people left in the city unscathed, and Annette automatically assumes he's a spy sent by Umbrella to uncover the G Virus. Even after she learns the error in her assumption, she's openly hostile towards Leon. In turn, Leon is skeptical of her and her motives. Understandable, considering she shoots him in the chest during their first encounter.
Sherry Birkins
Leon and Sherry hardly interact, but he does go out of his way to ensure her safety more than once. He does so in the B Scenario of Resident Evil 2, and in the one of the Resident Evil 3 Epilogues:
Leon Scott Kennedy is confronted with a man who claims to be a US government agent. Leon says, "Leave Sherry alone. She is innocent." "She knows too much." The man replies. He looks at Leon and says, "But you have value. This is a good deal. Make your choice." Without regret or hesitation, Leon closes his eyes and then sharply replies...
Like Leon did for Ada and Claire, we can assume Leon would go above and beyond his duty to protect Sherry. I may have said some harsh words about Sherry in the past, but didn't mean them. She was a cute addition to the game, and a sufficient member of the team. Unlike another individual who unfortunately must be mentioned next...
Ashley Gramm
Ashley Gramm is the president's daughter, and she has no qualms about flaunting her status. Leon's priority in Resident Evil 2 is bringing this privileged brat back to her parents intact. Ashley is the first character that we see Leon encounter in the game series that is completely helpless. Even significantly younger 12-year-old Sherry Birkins had stronger self-defense skills. Sherry skillfully evades enemies. Ashley will (seemingly intentionally) rush into their arms, then make Leon's (and subsequently, our) lives a living hell as we try to retrieve her before its "Game Over".
Aside from risking his life and going through hell throughout the entire game to save Ashley's ass, his interactions with her are scarce. If he does find her attractive, it's hidden behind a veil of professionalism. This is the president's daughter after all, and if he decided to take her for a test ride the secret service would find out (Ashley would claim Rape, isn't she just the type?) and blow his cock off. Smart move, Mr. Kennedy.
We would have been able to tolerate Ashley had she displayed the least bit of graciousness for Leon's courageous rescue. Sure, she tries to remunerate him by offering her cavernous, diseased twat for him to penetrate (Literally, by asking if Leon would like to engage in some "Overtime"- Not that any female with two eyes could blame her), but that's not as nice of an offer as an earnest, "Thank You." That, or should could have promised him she would speak only when spoken to for the rest of the ride home.
Luis Sera
Leon happens upon Luis Sera early in Resident Evil 4. Leon's interactions with Luis Sera show some of the remnants of trust Leon left back in Raccoon City 7 years ago. A tender interaction occurs early in the game with Leon telling him about his infamous 'first day on the job.' With a forlorn expression. Luis' assistance saves Leon's ass a couple times in the game. But his background and true motives are still mysterious. We get one of the more irreverent quotes in the video game from a Luis x Leon interaction.
Luis Sera: Have you got a cigarette?
Leon Kennedy: I've got gum.
Jack Krauser
Uhm, half robot, half man.... ALL Man? Who IS this guy? I'm not even sure. And I don't even want to know. Really.
Leon's relationship with Krauser goes back to the military academy, where these two received government agent training together. Soon after Krauser is introduced, we sense some animosity. Then engage in a knife fight. Their conversation reveals that Leon was lead to believe that Krauser died in an accident two years back. Krauser also admits to kidnapping Ashley Gramm and drops the "U" word. Horrors!
Ingrid Hunnigan
Her character just screams, "Unnecessary Last-Second Add-On," but regardless, she has become a part of the series and even had a brief cameo in Resident Evil Degeneration. Ingrid Hunnigan communicates with Leon via a high tech radio in the beginning and at the end of Resident Evil 4. She lacks the foresight to send Leon the army sized back-up he needs in any kind of timely manner. Oh sure, leave Leon to save the world alone, bitch.
Thanks to Leon's flirtacious quips with Hunnigan, we know that although Leon may not be able to forget about Ada, he's not about to force himself into celibacy on her behalf. Translation: Leon is not a complete pussy, and he's likely a putrid whore with an affinity for exotic brunette babes (he hits on 3 we know of).