29 Questions We've All Wanted To Ask Our Exes

My friends and I spend more time than I'd like to admit discussing our past relationships. And by discussing, I mean pondering over, occasionally pining for, and (always, without exception) lightly stalking our exes across various social media platforms. No one is proud of it, but sometimes all the unanswered questions that follow a breakup are hard to shake.
Enter my friend Judy. Judy is the bravest person I know. She's the type to scale a fence around a private beach without a second thought or saucily slide her phone number over to the bartender on a napkin. I've genuinely never seen her embarrassed or flustered — she's just cool. Anyway, during a particularly moony round of wallowing (on my part), Judy asked why we didn't just pick up the phone and dump all of our lingering queries on our actual exes, instead of each other. Thus, the challenge was born.
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Being far too much of a baby to do it myself, I dared Judy to have dinner with her former boyfriend of about nine months and ask him 29 of the most candid, no-holds-barred questions she could think of. I figured if the cast of Bravo's A Night With My Ex could do it, fearless little Judy could, too. Below, read the 100% real transcript of Judy's conversation with her ex, James. Fair warning: It just might inspire you to schedule your own recon mission.
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1. Judy: "What initially attracted you to me?"
James: "You had a mysterious and standoffish presence. I couldn't tell what you thought of me, and I wanted to know more."
2. Judy: "What are three things you think we have in common in this moment?"
James: "We both haven't seen each other since 30th March. We’re both enjoying papaya salad; I would venture to guess we both wish it were a little more spicy. We're both wondering about how the other feels in this moment."
3. Judy: "Can you pick an appetizer off the menu for me?"
James: "They're all super different. Do you want the crepe? With roasted mushroom sweet pea puree?"
4. Judy: "What was your least favorite memory with me?"
James: "The day I said 'I guess that's it' over the phone. Technically, the day we called it quits."
5. Judy: "How did we break up? I don’t really remember the specifics of that phone call..."
James: "I was waiting to get picked up for a company ski trip. We talked on the phone, and the gist of it was that my heart wasn't in it. I think I was just tired."
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6. Judy: "Would you say you broke up with me?"
James: "I don't remember exactly. I just remember being really sad. It was one of those conversations that teetered between whether to invest more and try to fix it or call it quits. We didn't try to fix it."
7. Judy: "If you could change one thing about our relationship, what would it be?"
James: "I wish I could have been more communicative. And for you, I think you weren't having a great time. You were having a hard time with work and that's tough on a relationship."
8. Judy: "Do you think you've changed from our relationship? In a better or worse way?"
James: "I don't think people change. I do think that after each relationship you're better at accommodating the needs of your next partner, though."
9. Judy: "What do you think was the most intimate moment in our relationship?"
James: [Laughs] "Buying poppers from the sex shop near your place. They obviously went unused but that doesn't diminish the intimacy at all... Okay, also, the weekend my grandmother died you came out to my parents' house with me. I didn't tell you that at the time — we didn't really know each other all that well yet. But I liked having you there."
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10. Judy: "What do you think we lacked in our sex life?"
James: "We could have used more of it."
11. Judy: "Favourite sex sesh?"
James: "My parents' house that weekend in May. We had sex three or four times in a row."
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Judy: "The weekend of your grandmother’s funeral?!"
James: "Well, when you put it that way..."
12. Judy: "What is your favourite thing about me, physically?"
James: "I really liked how I could just wrap my arms entirely around you when we were hugging. Like if I squeezed you hard enough I could consume you entirely."
13. Judy: "How are you feeling right now?"
James: "I feel fine. I don't want to be here. Want to come with me? To my house?"
Judy: "No! Not at all!"
James: "Okay. Too bad for me, I guess."
14. Judy: "Who would you say put more effort into our relationship?"
James: "There’s no real way to tally that up, but I’m willing to admit that I should have tried harder. I definitely didn’t bring openness and communication to the relationship — that’s something you provided. But I think I brought an unwavering foundation to the relationship."
Judy: "So I’m reading 'unwavering foundation' as you giving yourself credit for just being a part of the relationship."
James: "Let’s move on to the next question."
15. Judy: "Did you see yourself falling in love with me?"
James: "Probably. I certainly cared enough about you to feel that way someday."
16. Judy: "Is there any part of you that wants to try dating again?"
James: "There is always some part of me that longs for you."
17. Judy: "Is what you're looking for in a girlfriend different now that we've dated?"
James: "No, I haven’t narrowed it down. If anything, dating you has probably broadened my 'type.' You were very different from the other girls I dated. You’re more 'live-in-the-now,' and the others were very future-oriented. I like that about you."
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18. Judy: "Describe your dream girl."
James: "Smart, well-spoken, likes to have long, drawn-out conversations about things and maybe watch a Ted Talk or two. Also, someone I can run with."
19. Judy: What qualities do you seek most in a relationship?
James: "Laid back and calm with a little crazy mixed in."
20. Judy: "Do you think I'm crazy? Did you tell your friends that I'm crazy?"
James: "No."
Judy: "I think that you're lying."
James: "I didn't say you were crazy. I said 'bananas.'"
21. Judy: "Do your parents know about me?"
James: "Dad, yes. Mum, not sure. I don't like to talk to her about women anymore."
22. Judy: "Do you think there's anything we could have done to save us from breaking up? Or was it inevitable because of who we are?"
James: "I'm not sure — maybe a different time or a different place. You wanted to keep pressing forward — get into 'I love you's' — and I wasn’t sure that I wanted that yet."
23. Judy: "Would you say I put a lot of pressure on you?"
James: "Yes. You wanted me to be more communicative than I had ever been or was able to be. That was one of the things that brought us down — that I wasn’t able to give you what you needed."
Judy: "I feel like I did the right thing when I broke up with you. I mean, in my mind I broke up with you. I wanted you to disagree, but you didn’t. I feel like if you knew that's what I wanted in a relationship, you should have broken up with me first."
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James: "Well, I liked things how they were and I wasn't unfulfilled."
Judy: "That's so selfish."
James: "No it's not."
Judy: "You knew I was unhappy — I told you all the time."
James: "I thought you were being dramatic."
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24. Judy: "What kind of person wants a monogamous relationship that doesn't turn into anything more serious?"
James: "Um, pass."
25. Judy: "Describe a typical day in our life at 35 if we were married."
James: "We take off work on a Friday and have breakfast together. We probably have a toddler, and we take him out on our boat. We sail around, anchor somewhere, and spend the weekend there. That actually sounds really nice, doesn't it?"
26. Judy: "Do you think we will ever be friends?"
James: "I hope so, at the least."
27. Judy: "All in all, you’re saying I just wasn't the right person?"
James: "I’m saying it wasn't the right time."
Judy: "I don’t think I’m the right person."
James: "You don’t think I’m the right person?"
Judy: "No."
28. Judy: "Describe to me in detail how you feel about me now."
James: "You're a wonderful and fun-loving person with a very big heart. You deserve to have your needs fulfilled by someone."
29. Judy: "Would you have sat down with me when we were dating to answer all these questions?"
James: "Probably, yeah."
Judy: "You’re such a liar."
James: "You’re right. Probably not."
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