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Marrying Medic just for the tax benefits (he is only aware of this 10 years into the marriage)
And cheating on him with Scout, of course. Which also comes out upon hearing about the tax benefits. I mean, according to Demoman in-game, Medic is canonically a cuckold, it's canon-compliant in a way.
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Wonder if it's the other way around for the other team, Medic ends up sleeping with Demo's partner (who may or may not be eyelander)
Red vs Blu cucking lore goes crazy