Crisitunity!
That does suck about Doug and the ex, but hey, it means you don't have to feel awkward around either of them. If I were you I wouldn't hang out with them if it's just the three of you, I couldn't stand that.
Instead I'd take this as my opportunity to meet someone else, make some new friends (certainly keeping your old friends if you want), have some X3NO time, all that stuff.
If those two are going out now it means two problems have now just become one. Less to worry about, less to fuss over. And I don't think I even need to say this, but don't let yourself become Doug. Don't be the middle man, don't be the one they come to for advice, don't be a mediator. Mabye I'm too harsh but in my mind they're gone.
You know you're better off without her, and clearly better off without Doug. Doug knows what he's getting himself into, let them deal with it themselves.
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