Cindy Chupack
Can we talk about past loves with present-day sweethearts? The rules of remembering out loud.

Q: When is it okay to talk about exes with a new guy? I wanted to tell my boyfriend about my ex, but that made him uncomfortable. I did get him to open up about his past, then found myself walking on eggshells when I thought I was doing something he told me he hated about an ex.
— Jenny, New York

A: Greg Behrendt—whose new book, It's Just a Freakin' Date! (written with his wife, Amiira), comes out in December—once told me that when he met Amiira, they decided not to talk about past relationships. None! Zero! Zippo! "All we needed to know was that our pasts got us to where we were so that we could meet each other," he explained.

I found this astonishing. First of all, what did they talk about? I usually spent my first few dates performing my one-woman show, Why a Great Gal Like Me Is Still Single and—if the guy hadn't left at intermission—listening to his one-man show, I Musta Been Crazy Not to See She Was Crazy. Then I spent the next few dates trying to ascertain how skinny his exes were without seeing photos or asking him directly. I thought this was a necessary part of the mating ritual. Turns out it can be skipped, like dessert!

I remember in Jerry Maguire, Renée Zellweger's character starts to talk about her past marriage, then stops herself and says, "Let's not tell our sad stories." So that's what I was going to suggest, Jenny, that maybe we shouldn't tell our sad stories, because you often get more than you bargained for. For example, I used to think I was open to hearing about a boyfriend's ex as long as the point was that I was better/nicer/smarter/saner than she. But even then, a boyfriend might accidentally reveal too much, as in: "I'm so glad you don't need to bring other women into the relationship. Believe me, a threesome is not as great as it sounds!" I got that sad story once and never fully recovered.

Then again, my entire relationship history is available in paperback, so what do I know about discretion? Before giving advice, maybe I should seek advice from someone better/nicer/smarter/saner than I. Thus I called Toby Salter, a Los Angeles-based marriage and family therapist, and she thought the idea of bottling up our sad stories was the saddest story of all.

Although she admits that therapists have a different perspective—they believe your past makes you who you are—she also believes the intimacy of the disclosure should reflect the intimacy of the relationship. For example, if a guy buys you a drink, you don't need to thank him by telling him about the bastard who broke your heart, but you're certainly allowed to discuss the bastard once you get closer. "Openness, honesty, and the freedom to reveal yourself is what love is all about," Salter says.

The bigger question in her mind, Jenny, was why your boyfriend didn't want to hear about your past. What scares him (or any of us) about knowing everything about a partner? And as far as "walking on eggshells," Salter says: "If you're contorting yourself into being someone to get someone…you should stop to wonder why you're auditioning."

So although you don't have to share everything—or anything, as Greg and Amiira proved—you shouldn't be afraid to talk about your past. If your boyfriend can listen to your sad stories and accept you for who you are (and who you were), maybe he's your happily ever after.

Cindy Chupack is the author of The Between Boyfriends Book (St. Martin's Griffin).


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