“So Tell Me About Your Past Relationships…”

"So Tell Me About Your Past Relationships..."

Indeed, it’s a question many women are tempted to ask on a date …and it makes men cringe. Here’s how to discuss former flames with finesse.

By Steve Friedman

“So,” she said, on our second date, after dinner, after a casual exchange of professional resumés, after lingering smiles and downcast glances had convinced us both (I think) that chances were good for future dates... “So,” she said, “tell me about your past relationships.”

She was smiling, but all I saw were sharp teeth. Danger. This is because I am a man.

Six simple words, but I froze. Should I mention the woman who dumped me, who I then decided would respond favorably to a stream of loving emails and cheesy poetry, until she suggested I lose any and all information I had regarding her since it would really be more pleasant for all if legal authorities didn’t need to be involved? No, I decided, something told me that might not be the best answer.

Perhaps I should mention the woman who fell in love with me, the sweet analyst who liked to do crossword puzzles and who baked me blueberry pies and introduced me to her parents and who went out with me for two years before I broke up with her because... well, I was still trying to sort that out.

No, I decided. Some of the details of that story might help my case here, but there would be the follow-up questions to consider. The “why’s.” I didn’t want follow-up questions. I wanted to avoid ‘why's.”

Maybe, I thought, I should go all Zen on her. As in, “You know, it’s so great being here with you, in the moment, I don’t want to distract myself by bringing up the past.”’ Ugh. That sounded bad even to my ears.

Then I got irritated. (Of course, all this happened in approximately 2.5 seconds; date time is a strange and weird thing.) Why was she asking about my past relationships? Why do all women want to know about past relationships? What's their problem?

Their problem, or so I’ve been told, is that women tend to be inquisitive and intelligent creatures, constantly gathering data and sniffing the air before making big decisions. “Kind of like those cute little prairie dogs,” says my friend Jack, who dates a lot, but never for long. “They want to make sure there are no hungry predators around before they move to a new little prairie home.”

“That’s absurd,” says another friend, Lizzie (who happens to detest Jack). “Women ask because they want to get to know a guy. All they want is some information.”

Both Jack and Lizzie are right. And that’s the problem. When a woman asks a guy to tell her about his past relationships, what a guy often hears is this: “What are you doing without a girlfriend?” Or “What's wrong with you?” Or, “What red flags should I, cute little prairie dog-like woman, be watching out for?” Here, a guy’s point of view on the best way for a woman to gather the information she craves:

  • Don’t ask until you know each other. That might happen on the third date. Or the fifth. Or the tenth. It won’t happen on the first or second. How can you be sure when the right time is to ask? Here’s a rough guide. Sometime after the first kiss that lasts longer than three seconds. Sometime before you plan a weekend trip together. Wait too long, and you might learn about the restraining order when it’s too late to do you much good. Ask too early, and you might sound more interested in his past and your collective future than you are in him.

  • If you can’t help yourself and do ask early on in the dating relationship, and the answer is “I'd really rather not get into that,” smile, offer assurances that you meant no offense, and proceed with some—but not too much—caution. I mean, his is a perfectly reasonable response. If he gives the same answer after he’s asked you to accompany him to Belize, proceed with lots of caution.

    And when you do ask? And when he does answer? Listen closely, because there are warning beeps audible to the careful listener. Here are a few:

  • “She was psycho.” This means he isn't taking any responsibility for the failure of the relationship. Either that, or he likes psychos. Neither indicates a happy and healthy future.

  • “I just haven't met the right person.” That's OK if he's younger than 35. But after that, he's probably met at least one or two “right” people. Blaming his loner status on others may mean he blames a lot of choices he's made on others. Not good.

  • “Women just don't understand me." If they don't, then you won't, either. Finish your drink, and say goodnight.

  • What if he says "I've spent the past few years getting to know myself and I think that until now I haven't really been emotionally available to anyone, but now I am"? Well, that means he's either a world-class con artist, or he's remarkably self-aware and romantically intriguing. How do you find out which? That's what the next date is for.

    Speaking of which, what if he throws the ball in your court and asks about your past relationships? Some pointers:

    Be careful. What if you wanted the relationship to move forward with more of a commitment, and he was perfectly happy seeing you only two nights a week and “not getting too serious”? No need to call this possibly emotionally stunted individual names. “We wanted different things” will do just fine.

    Be selective about your bad behavior. Your last relationship didn't work out because he caught you in bed with another man? Or because you got drunk at your boyfriend's company picnic and flirted with his boss? Boil that down to “We eventually learned we were better as friends than sweethearts.”

    Be selective about his bad behavior. You split up because when your mother died, he declined to accompany you to the funeral because it interfered with his weekly golf game? Or because you found him in bed with his coworker? Or because he called your best girlfriend “a controlling harridan”? “He seemed like a really sweet guy, and it took me awhile to realize he wasn't,” will do.

    Be honest, but not too honest. You haven't had a sustained monogamous relationship that's lasted for more than three weeks in the past ten years, and you desperately want to have a child and you see a shrink four times a week to figure out what's wrong? Here's how to package that: “Until recently, I haven't been sure I wanted a relationship. So it was probably my fault as much as anyone's that none of my romances lasted very long. But now I'm more clear on what I want and don't want. And one thing I want is honest and open communication.” Guaranteed, this will stop most any guy from asking any more questions.

    Steve Friedman is the author of seven books, including Lost on Treasure Island: A Memoir of Longing, Love, and Lousy Choices in New York City. More information at

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