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Sometime during the Infinity War [yes, another one because my brain can't stop and this one came out so long oops]: (1/3) Loki and Tony have an affair. Suddenly the Grandmaster arrives and finds out about Tony and is so heartbroken like "Oh you wanted someone younger, but sweetie it's gonna backfire on you so quickly because in a moment he'll look way, way older than me or be dead" and Loki says "I know. He's only 50 but already looks like he's 3000."