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All this information came up over the course of our 10-hour date, and to some extent, the process of James discussing it was akin to someone waving a red flag in my face. The point of course is this: There are some serious pros to dating a divorced guy. The Cons: (I thought we’d get the negatives out of the way first. ” You’ll have to manage her continued pining, her continued pursuit. You will see him see old photos, you will see him cry or scream or fume or mourn. And – lest it bears mention – this is all as much fun as… A guy who’s lived with a woman for a significant period of time has a pretty good sense of what to say and when to say it. If you’re boyfriend’s divorced, you can be 99 percent sure he’s lived with someone else for a while and has a solid understanding of shared space as a result. A divorce is a horrible thing to be sure, but from what I’ve observed, it’s also pretty humbling.