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Why This Dating Coach Thinks You Should Reconnect With Your Ex

Kelly Gonsalves
September 22, 2019
Kelly Gonsalves
Contributing Sex & Relationships Editor
By Kelly Gonsalves
Contributing Sex & Relationships Editor
Kelly Gonsalves is a sex educator, relationship coach, and journalist. She received her journalism degree from Northwestern University, and her writings on sex, relationships, identity, and wellness have appeared at The Cut, Vice, Teen Vogue, Cosmopolitan, and elsewhere.
September 22, 2019

How can you learn to be a better person in your relationships?

I recently discovered one of the most powerful and admittedly terrifying learning methods for this endeavor that I've heard in a while. In the pages of her new dating workbook The Game of Desire, popular sexologist Shan Boodram suggests the unthinkable: Reach out to your ex and get their honest opinion of you as a lover.

"Our exes are road maps," Boodram tells me over the phone. "They are a part of the breadcrumbs that make up who we are, how we like to be loved, and how we don't want to be loved in the future. They are important gems of information that can be tapped into."

Here's how it works: Boodram recommends reaching out to an ex-partner to have a sincere, honest, peaceful conversation. The purpose of the activity isn't necessarily to create closure or to smooth over any lingering tensions, she emphasizes. Rather, the purpose is to get a clear window into what you specifically were like in the relationship, what your strengths were, and what made you challenging to be with.

A few of the questions she recommends asking:

  • Was I a good listener to you?
  • Did you find me reasonable?
  • Was I too sensitive or emotionally unstable?
  • Was I emotionally unavailable or distant?
  • Did I make an effort to understand and meet your needs?
  • Did I apologize often and effectively to you if I was in the wrong?
  • Did you consider me an independent person or a needy person?
  • Where do you think we were incompatible?

(There's a whole worksheet with more ideas in the book as well!)

Boodram says this exercise was inspired by the teachings of philosopher and author Alain de Botton. You might remember his widely shared essay in the New York Times from 2016, "Why You Will Marry the Wrong Person." A key message Boodram took away from his teachings on the subject is "the lack of self-work, self-insight, and emotional intelligence that we have that really prevents us from making logical decisions on who we should partner with," she explains. We don't know ourselves well, we can't see our flaws clearly, and so we continue to make the same mistakes in our relationships—and end up in relationships that simply don't suit our true needs and our authentic selves.

By reconnecting with your ex and asking them to give an honest assessment of you as a partner, you're able to receive a kind of report card—just like in school—that can help you identify the areas that you need to work on and also start to understand the types of dynamics you're more likely flourish in.

"When it comes to relationships, period, we really aren't getting these enhanced assessments as to what we're doing wrong, where we're coming up short, and a real picture of our strengths and weaknesses, which makes it difficult for us to decide who we should partner with long term," Boodram says. Your family and friends might be able to give you some of that information, she says, but because they don't have to go home with you at the end of the day, they might not actually know what you're like behind closed doors or in a truly intimate relationship with vulnerabilities on full display.

"Your exes hold a wealth of information as to what it's like to be romantically connected with you," she says. "There were sides of your personality that you wouldn't show in a friendship, and if you're trying to learn how to be a better intimate lover, that's the best source."

So I guess Ariana Grande was on to something: Every past relationship in our life can be a lesson for us to grow into better, stronger, kinder people—provided we really take the time to be truly open to learning from them.

If you want to give it a try, here are a few important things to keep in mind when having this conversation with your ex.

How to have a productive, enlightening conversation with your ex:


Pick the right ex.

"This is not an exercise to go back to the ex who didn't mean well for you while you were together, the ex who you were only with because you were going through a really tough time and you were deeply insecure and that person played on your insecurities," Boodram says. "That kind of individual doesn't have the tools to improve themselves, so they're not going to have the emotional intelligence to give you tools to improve yourself."

The right person for this conversation is someone who generally treated you well and had your best intentions at heart. It's not necessary that the relationship ended on mutual or pleasant terms, she says, but perhaps it was a "right person at the wrong time" situation or a relationship that ended poorly simply because you were young and didn't have the tools to end it well at the time.


Stay on task.

When you initiate the conversation, be sure to state your intentions up front so your ex isn't wondering about your motives: Tell them you think positively about your past relationship, you've moved on, and right now you're working on your own personal development and want to ask them a few questions about how you showed up in the relationship.

And remember: Closure or peacemaking is not your goal here. "I also did this exercise, and when I first did it, the person who I was speaking to was making these really general statements like 'we didn't really communicate well' and 'we were never on the same page,'" Boodram says. "I had to stop him and say, 'This is not figuring out why this didn't work. It's been so many years. I'm OK with the fact that it didn't work. I need to learn what I have to work on. So that's what this conversation is about.'"

Stay on task and make sure the format of the conversation is you asking questions about what you were like and your ex talking about their thoughts on you, your behaviors, and your actions. Don't deviate to "more neutral ground that actually isn't progressive for you," Boodram says. "This is a CTA phone call. This is a call to action for you to say, here's what I know I have to work on, here's what I know I have to reflect. So if you have a conversation that's more vague, more about the relationship, and more about peace and closure, you might leave that feeling better but actually not having any tools to be a better person."


Joint responsibility is not your focus here.

For once! In general, a lack of accepting joint responsibility is exactly what can drive couples apart. The two sides fail to recognize how they're jointly responsible for their conflicts. We're often quick to point out what the other person has done wrong but tend to be blind to how we ourselves have also contributed to the trouble.

This exercise is an opportunity for you to do the exact opposite: put your finger away and put the spotlight on what you did wrong. That means it's important to avoid getting defensive or jumping in to point out how your ex did bad stuff too. (A "battle of the egos," as Boodram calls it.)

"A report card is not a mutual assessment of how your teacher did. It's really just an assessment of what kind of student are you," Boodram offers as a comparison. "As much as I think our ego wants to make it about joint responsibility, I don't think the value of it will be as fruitful if you go that route versus just focusing on, how did I suck in this relationship?"

You can always have another conversation separately if you want to hash out the details of how you both contributed to the relationship's end, but for the purposes of this exercise, you're here as a listener and learner.

This isn't easy! It's OK if the conversation is daunting, damning, or just extremely uncomfortable for you. You'll hopefully gain a lot of insight from it, and if you're willing to really reflect and improve on what you learn, you and your future relationships will be all the better thanks to it.

Kelly Gonsalves author page.
Kelly Gonsalves
Contributing Sex & Relationships Editor

Kelly Gonsalves is a multi-certified sex educator and relationship coach helping people figure out how to create dating and sex lives that actually feel good — more open, more optimistic, and more pleasurable. In addition to working with individuals in her private practice, Kelly serves as the Sex & Relationships Editor at mindbodygreen. She has a degree in journalism from Northwestern University, and she’s been trained and certified by leading sex and relationship institutions such as The Gottman Institute and Everyone Deserves Sex Ed, among others. Her work has been featured at The Cut, Vice, Teen Vogue, Cosmopolitan, and elsewhere.

With her warm, playful approach to coaching and facilitation, Kelly creates refreshingly candid spaces for processing and healing challenges around dating, sexuality, identity, body image, and relationships. She’s particularly enthusiastic about helping softhearted women get re-energized around the dating experience and find joy in the process of connecting with others. She believes relationships should be easy—and that, with room for self-reflection and the right toolkit, they can be.

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