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Because I don't support someone being with more than one person.
I think he should get with Claire sometime down the RE Timeline but it will probably never happen sadly enough.
I hope not. They're friends, not romantic.
Edward is edward as always but I don't get why you'd want to further ruin your life if your beloved one rejects you. I mean its both logical and smart to just continue through your life and find a new girl. Theres billions of them in the world, millions in every country. Though this may just be your personal experience (with that girl in 6th grade or whatever), its not a correct way of thinking.