Briarwood has slept around, in fact, he's pretty much a manipulative dickwad - so in order to get what he wants, he would probably engage in flirting. And then crush everyone's dreams.
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I should point out Nicolai is at least bisexual, I've never used him with women before though as I'm horrible with straight couples, So don't be surprised if flirting happens. Nicolai is extremely cocky xD