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Play it safe. If the girl was worth it, she'd accommodate you.

Aren't you neglecting to consider the (in these days, very real) chance that it is worth him accommodating the girl, rather than the other way around?

Both he and she could have substantial reasons making it worth being accommodated by the other. I wouldn't assume that only the boy is worth accommodating - especially since he's in tech, where there's a lot more flexibility than usual for working remotely, etc.

Working relationships are about compromise. Without compromise all you're left with is parasitism. Take this morsel of wisdom from a happily married man.

But why should she compromise for him? By your wisdom shouldn't there be mutual compromise?

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