Living Repurposefully

To quote the Facebook relationship status, "It's complicated." I went out with this man a few times and slept with him once. It didn't work out, and now his sexy guy friend, who's also his boss, has asked me out. However, the boss guy used to date one of my female friends. We are all in the same social circle. What's the protocol here? Do I need to ask permission or give anybody a heads-up about my going out with the boss guy?

--Messy Picture

It can be a little touchy for all involved when everybody's answer to "Where have you been all my life?" is "Having sex with your friend." But perhaps you missed the news. They passed an amendment against owning people. In, uh, 1865. So, assuming your girlfriend isn't in a fetal position behind her couch sobbing over the boss guy, you should feel free to go out with him. But considering how often first dates end up being last dates, it's best to avoid putting out a press release about your plans. If dating the guy does take a relationshippy turn, that's when you give your girlfriend a little heads-up: "Hey, just wanted to let you know, I was rummaging through your trash and I found this fabulous old chair, along with your ex-boyfriend." Stay classy -- that is, avoid any temptation to go gloaty: "They both are, like, so comfy and are really perking up the bedroom!"