Ok since Ashley and Leon are canon in RE4R, do you think there's a way for them to actually be together? Isn't their situation pretty much impossible since she is the president's daughter and the president's is Leon's direct boss.
I would love to see more of Ashley in the future and to see her interact with Leon after RE4, but I honestly don't see how they could have a relationship, mostly because I feel Leon wouldn't allow himself to get too close to her with his position as an agent and because he probably hates himself and think she deserves better.
What do you think?
The realistic and honest answer is: Leon and Ashley will never be together because Capcom will never commit to the ship, because they don't commit to ships in RE. The only reason why they ever committed to Aeon was because Hideki fucking Kamiya was the director of OG RE2, and he doesn't give a fuck. So, once Kamiya already made a kiss and a declaration of love canon, Capcom was like "welp. I guess we're stuck with that."
The more story-based answer is: President Graham resigns a few months after RE4 (like, basically right after Infinite Darkness) so it's not like Leon and Ashley are going to be stuck in limbo for four or even eight years of her dad's presidency. And, chances are, Leon consciously decided to give Ashley some space after returning home because he didn't want her to become dependent on him.
So, by the time President Graham resigns, that's probably around the time that Leon would want to reach back out to Ashley anyway just to check on her and see how she's doing -- especially since her dad is leaving office and it's not like he'll be able to just drop in on her whenever anymore.
So, the whole "boss's daughter" thing, I don't think would be an issue.
I also don't think that Leon's self-loathing would be an issue, either. I've said it before in previous meta, but I am not entirely sure that Leon actively realizes that he's started to feel some type of way about Ashley -- or, if he does, he's purposefully repressing it. So, I think any developing relationship would happen the same way. I don't think Leon would realize just how serious or intense things were getting until it was too late for him to just back down.
And then, at that point, it's like... A serious conversation has to happen. I don't think Leon's #1 thing would be "I'm not good enough for you." I think it would be more along the lines of "I don't want you to put your life on hold for me." Because, realistically, he can't just commit to being a regular boyfriend type of guy. He has no way of knowing when or even if he'll be around or for how long. He'll inevitably end up missing birthdays and anniversaries and weddings and funerals. They'll never be able to plan anything around his schedule, and he'll never be able to promise her anything, because any promise he makes is one he might not be able to keep.
There's also the issue of basically everything Leon does in his job/life being classified. Would he be willing to share his life with someone that he can't actually... share his life with?
So, at most...? I would see Leon and Ashley having the ultimate on again/off again relationship between his missions -- where, he disappears into radio silence for months on end, but then he inevitably drops back into her life for a few weeks of constant companionship and dates and hot sex, and every single time they tell each other "This has to stop, we can't keep doing this" because it's not fair to either of them emotionally, but it never actually does stop, because the emotions are real, and they both want the relationship to be real, but it just... can't be.
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