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My friends and my rule of thumb is if he is a real ex (from a relationship that had a title and lasted months/years) then he is off limits. Even if you've moved on and your over him. It's not worth bringing-up old memories or making things awkward.
I'm getting married in a month, but if one of my friends started dating an ex-boyfriend of mine, things still would be pretty awkward whenever we would run into each other or talk. I'd be happy they're happy, but it still would be awkward.
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