My girlfriend just asked me to go out to dinner with a male friend of hers that I have never met and whom she often talks about. I have a feeling she's had a previous relationship with this guy, and it doesn't seem like a good idea for the three of us to have dinner. Should I ask her if she's been with him in the past, or ignore it and go out to dinner?
He Said: I'm concerned that you don't already understand the context of your girlfriend's relationship with this "male friend." Whether he's "just a friend," a former lover, or something else entirely, it is the kind of significant relationship that ideally should have already come up. One of the great things about a budding romance is sharing your take on past friends, hookups, and lovers, and it is one of the ways we understand how we fit into each other's relationship history. It’s how we figure out how to turn each other on—and off. It’s one way we avoid making the mistakes of past loves. It’s how we turn jealous rages into fodder for great passion.
Now you may well decide, after a long conversation, you prefer a "Don't Ask, Don't Tell" (can we still use this military metaphor even after Obama killed the policy?) arrangement in regards to this male friend, and perhaps others, but you will only know this after your conversation. Rather than being accusatory about this lapse (it may be your lapse as well), tell her how much you want to share both your pasts in order to help create a great future. So, yes, by all means: Do Ask, Do Tell before agreeing to dinner.
She Said: Hear hear. Especially the part about turning jealous rages into fodder for great passion. Though you may get there eventually, it sounds like you and your girlfriend are at more elementary stage of your relationship right now. By the time some San Francisco couples get together in their thirties or later, there can be literally hundreds of past lovers between them, especially when you count one-night-stands and friends-with-benefits. So it may not be so surprising that you haven’t yet discussed this particular friend.
What concerns me is that you are considering just ignoring the question and going out to dinner, even though your gut says that’s a mistake. You need to calmly and honestly say something like this to your girlfriend: “Have you ever been more than friends with ___? I ask because, if you want to remain friends with past lovers, I’m okay with that, but I’d like full disclosure if you’ve slept with someone, and I’m not really comfortable having dinner with them.” That should start a conversation. The fact that she mentions him a lot can either mean they simply hang out a lot (if that bothers you, say so), or that she still harbors some lingering attraction to him. But during your talk, try not to overreact to anything you learn. We all have the tendency to dramatize and enlarge past lovers’ importance in our partners’ lives, but by and large that’s an illusion. The important task is to decide what boundaries you’d like to have around ex-lovers and communicate them to your girlfriend, whether that means you refraining from having dinner with him or asking her not to have dinner with him at all. It’s your turn to be the main character in her life. Show her—and yourself—how strong, honest, and self-knowing you can be.
“She” is Robin Rinaldi, 7x7’s former executive editor, currently at work on a memoir titled The Wild Oats Project.