Leon's flirting in Infinite Darkness
This scene has, since day one, been one of my favorites in Infinite Darkness. The series did an excellent job at bringing a lot of aspects of Leon's character to the surface. Things we were already very familiar with, like his kind and attentive nature, but also darker aspects of his character he generally tends to keep hidden, such as his anger, his resentment, and the extent of his trauma regarding Raccoon City. What I love about this scene is that it is also a prime example of one of those darker aspects of Leon's character. One that is integral to understanding who he is as a person — his desperation.
I've seen the idea of his flirtation with Shen Mei in this scene being interpreted as platonic become popularized. For some people, choosing to ignore what is being presented here is easier than accepting that Leon S. Kennedy would ever be okay with going on a date with someone already in an established relationship. Though I think that idea discredits the deeply human sentiment present in this scene. As morally objectionable as Leon's actions are here, there's something incredibly authentic about them. Unknowingly, he's disclosing his desires, and not just sexual ones.
It's very clear that Leon is asking her out to dinner with romantic intent. This comes down to my own personal life experience, but I've come to understand this as a universal truth: when a man you hardly know asks you to do anything with him, it's a date. He is asking you out romantically, guaranteed. In the case of Leon in this scene, when you take the context of Shen Mei being in a relationship and Leon's lifestyle into account, you can paint a clear picture of him not only asking Shen Mei out on a date, but he's doing so to get his foot in the door, so-to-speak.
He's not looking for longevity, he's doing this with the sole intention of sleeping with her. That's why he disregards her relationship — approaches this with a shameless 'I'm willing to be the mistake she makes at least once' mentality — because he's not looking for a relationship. He's desperately yearning for pleasure; for the burdens of his life to melt away, even if the moment is fleeting. Even if it comes at the cost of someone else's relationship. An act of selfishness — something we don't often see from Leon — but desperation has a way of making people act impulsively. I think this speaks volumes about his character.
Leon lives a life that doesn't allow for him to be able to settle down. Given how compassionate and empathetic he is, he more-than-likely views relationships as impractical at best. He'd constantly feel like his happiness would come at the cost of his partner's, and that's not something he could live with, so he submits to loneliness. It's practical, it's fair, and it's the only option that makes sense given his career. A long-term committal relationship is just another opportunity his service to the government has taken from him, and while he can have it, he will not willingly drag someone else into a relationship that would surely be filled with disappointment to do so.
So instead, he seeks momentary pleasure. He flirts with women like Shen Mei and Hunnigan while on duty. He self-sabotages by pursuing emotionally unavailable women like Ada. One could argue that flirting with Shen Mei and Hunnigan are also him self-sabotaging, as they are also women that are most-likely going to reject him due to the professional nature of their relationship. He's going out of his way to avoid genuine connection, and therein lies the tragedy of it all.
At the end of the day, he craves normalcy. He yearns for a life he can't have and deeply resents being denied it. Moments like this are just displaying how Leon navigates the circumstances of his life, actively denying himself a happiness he is so deserving of, but deems as unfair to others. He wants to feel needed and appreciated in a way that makes him feel like anything other than a weapon pointed at the government's problems — to feel loved, in the most intrinsically human way possible, even if it's only for one night with someone and ultimately means nothing in the end.
This moment perfectly encapsulates something that has always been a crucial component of Leon's character, the extent of his tragedy — the lonely and isolating nature of a life he didn't choose.
