DEAR HARRIETTE: I was out at a bar with a girlfriend of mine when we ran into a man I used to casually date. She couldn’t stop talking about how handsome he was, and she even asked me to set them up. I didn’t mention that we have a romantic history because it didn’t seem worth mentioning at the time. We weren’t serious at all. He and I don’t even speak anymore unless we run into each other somewhere.
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Is it important to tell my friend about our history before I introduce them? She probably wouldn’t be interested if she knew we used to see each other, but I don't want her to pass without giving him a chance. He was a nice guy, and they might really get along -- he just wasn’t right for me. What do you suggest I do? -- Brief History
DEAR BRIEF HISTORY: Tell her now. This saves any misunderstanding in the future. Be honest and simple. Yes, he is a nice guy. You know that firsthand because you went out with him before. He wasn’t the right fit for you, but not because there was anything wrong with him. He just wasn’t your guy. Avoid going into every little detail about whatever history you do have, including the level of intimacy you reached. That is none of her business. But you can be upfront about the fact that you went out with him.
Make it crystal clear that you do not mind at all if she goes out with him -- or even if she marries him. You want to be direct about this because very often people want their exes to remain off-limits for life to their friends. Since this is not the case, make sure your friend knows.