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The VN or the games gave kisses and there were hookups if I remember correctly, but it drew the line with wedding dresses. No weddings in-game, but the girls tried on the dresses, giving obvious implications that wedding should be a future step for the couples.
So despite routes and whatnot, the canon wedding couldn't be threathened with a non-canon wedding in the games. At least that's how I remember these things. I could be wrong.
A spin-off manga taking place in the present timeline post-wedding, even without any sort of romance could be fun, but Negi shouldn't supervise it in my opinion. It feels like WSM/Kodansha constantly tests the staying power of the work, yet not attempted to do anything within the universe. Once Naito Marcey finishes Amagami-san, they should really persuade him to do some adult spin-off for the quints. He was once Negi's assistant and some of his designs are reminiscient of the quints in my opinion.
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