Questions to ask your boyfriend about past relationships

Sometimes, when relationships break down, the reasons are clear: they cheated, you cheated, one of you moved away, you drifted apart, you fought all the time, you wanted different things. But sometimes you have no idea what happened, because the person was so afraid of hurting your feelings during the break-up that they hardly say anything at all, leaving you to draw your own conclusions, put two and two together, and come up with a story that could be so far off the mark, but which you and your friends think is the most likely explanation. So that becomes "what happened." In these cases, the relationship can stay hanging in the wardrobe of your past for years. So when enough time has gone by that your feelings probably won't get hurt, what is the harm in asking? Saving face is so 2010.

Eight years ago on Valentine’s Day, my boyfriend of four years, who I planned to marry and love forever, was waiting outside my work with a huge piece of my favorite cake. We went back to my place, watched Requiem for a Dream (widely regarded as one of the most depressing films ever made), and broke up. Seven years on, I still joke that Requiem for a Dream was the reason he dumped me, since from my perspective, everything was totally fine until that point. I was devastated and didn’t understand what had happened, asking if he liked someone else, if he was bored, the usual questions — he said no, not really, he just didn’t feel the same anymore. I told myself I must have missed the signs, and privately suspected he'd cheated on me with that woman from his work.

Roll on to present day. We’re both in happy relationships and keep in touch a bit over email but haven’t seen each other for a few years. He's not on social media, so there's nothing to stalk, which is nice. When I emailed him to ask if he’d be willing to answer 29 highly personal questions about our relationship and the real reason we broke up for an article, he said sure, send them over. My colleagues cringed at the questions when I showed them, but now I have all the answers, and it turns out I was right about Requiem for a Dream.

1. What initially attracted you to me?

"Your unconventionally beautiful face, luscious hair, and good chat."

2. What do you think initially attracted me to you?

"My conventionally beautiful face, shaved head, and good backchat."

3. What is your favorite memory of me?

"Two things come to my mind. 1) Building an adult-sized igloo with you and your family in your garden at Christmas. 2) Sitting side by side on the front row of the Nemesis Inferno rollercoaster at Thorpe Park and doing the unconditional 'no fear' handshake we used to do."

4. What is your least favorite memory of me?

"Aside from breaking up… looking after you one night when you were drunk. I sensed a vomit eruption was about to happen so [I] grabbed the nearest bin, only to find the bin was perforated. Carrying you half-conscious to the shower to then wash the sick off both of us, covered in sick… well, say no more. But I will, because then I put on marigolds and scrubbed the sick off the carpet, at 4 a.m., with baby wipes because there was nothing else."

5. Why did we break up?

"Things had started to take off at work for me. Things had definitely taken off at work for you. I think I was in too much of a routine. I didn’t like waiting outside your work for you all the time. Things started to annoy me more. I wanted more attention. You started to do drugs. I fancied other girls. I needed some independence."

6. Describe the night of the break-up, from your point of view.

"The break-up, in my mind, started from the moment we finished watching Requiem for a Dream. That film was so emotionally destroying, I don’t know, it’s like it gave me the push to do it somehow… it was the straw that broke the camel’s back. I thought breaking up was the right thing to do, so I did it, but it was horrible. I’d never broken up with somebody I loved before. That night was a messy blur, but I remember calling my best friend halfway through it for emotional support, but he couldn’t speak because he was in the cinema! I had second thoughts throughout, but I was too stubborn to change my mind."

7. What was I like as a girlfriend?

"Great. You had your good points and bad points, but I certainly fell madly in love with you to the point of obsession. You had your own sort of way about showing love and affection, though. I’m a naturally affectionate person: kissing, touching, hugging, saying things, messaging things. You weren’t like that. I remember I used to call you Ice Queen. But I think I only called you Ice Queen because you said your previous boyfriend also called you Ice Queen?! That being said, I did feel loved. And love and affection aside, you were super fun. Great sense of humor. Outgoing. You always wanted to do stuff, or had something interesting to do (most of which was work-related, not that that matters). You were great with my family. My mom thought we’d be together forever, and you’ve been the benchmark ever since. You were so easy to be around and you were also my best friend."

8. What did you learn about women from going out with me?

"That they are often like their mothers."

9. Was there anything I did that you found really annoying but could never tell me?

"Took work too seriously."

10. What were my worst traits as a girlfriend?

"This is being fairly picky but: working too much, being quite cold with affection, and not being able to cook, lol."

11. What were my best traits?

"Intelligence. Sense of humor. Very attractive. Fashion sense."

12. What would you have done differently in the relationship?

"I wish I’d been less intense, less obsessive, less controlling. I wish I’d included you more in stuff I did with my friends. I wish I’d been more honest and open with you at the time about the stresses and the strains I thought were affecting our relationship."

13. What did you do differently in your next relationship after me?

"I learned to compromise. I was less moody and less obsessive."

14. What do you think was the most intimate moment in our relationship?

"That time I thought I saw a ghost, or a devil, and started freaking out about religion. You were so kind and empathetic. Never felt more for you than I did that night."

"Hopefully I’m not alone in thinking this, but nothing."

16. What is your favorite thing about me physically?

17. Who were you sexually attracted to more, me or your girlfriend before me?

18. How many times did you seriously think about cheating on me?

19. How many times did you cheat on me?

20. What! I thought that was the reason we broke up. How long did you wait until you got with someone else after the break-up?

"I think just over a month. Safe to say that was a disaster."

21. What did you tell your girlfriend after me, about me and our relationship?

"That you were my first love."

22. Who would you say put more effort into our relationship, you or me?

23. Would you go out with me again, given the chance?

24. Do you think we should have got back together?

25. Can you remember our biggest argument (besides the break-up)?

"The night I found out you'd done drugs."

26. Having been out with me, what do you think I need to be happy in a relationship?

"You need a rock, a best friend, and a good sexual partner."

27. What did your parents really think of me?

28. Describe a typical day in our life at age 35 if we were married.

"We’d be living in another country in a super cool house. You’d be at home writing your third novel. I’d be at work doing God knows what."

29. Describe our relationship now.

"It comes and goes, but it’s a very easy friendship. Something more will always be there, which is beyond my control, but it’s like those lifelong friendships everybody has where you go years without seeing someone and then when you do, you just pick up where you left off, as if nothing had happened in between."

What should I ask my boyfriend about past relationships?

7 Questions To Ask Your Partner That Can Reveal How They Truly Felt About Their Ex.
"Who Broke Up With Who?" ... .
"How Long Ago Was The Breakup?" ... .
"What Did You Two Used To Do Together For Fun?" ... .
"If You Could Do It Over Again, What Would You Have Done Differently?" ... .
"What Was One Thing You Really Disliked About Your Ex?".

Is it healthy to ask your partner about their past relationships?

“It might feel awkward at first, but it's also perfectly healthy to talk about past relationships if it's done in a conscious way. It can help you understand each other better when you share these things; it can alleviate any fears you might have.

Is it good to talk about past relationships with your boyfriend?

You might feel awkward discussing exes with your new partner, but having an honest conversation with them about past relationships is perfectly healthy. It can bring you closer together and help you to better understand your significant other, and vice versa.

What are some serious questions to ask your boyfriend?

Serious Questions to Ask Your Boyfriend.
What makes you the happiest?.
How can I support your interests?.
Do you hold grudges?.
How would you describe your family?.
Tell me about your relationship with your parents and siblings..
What do you want to improve or change about yourself?.
Do you have any regrets?.

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