Hey, listen, I know it was 20 years ago, but can I please get my sweatshirt back?
In two very different ways the only two that have mattered would be unable to answer honestly due to mental defect/mental illness. Not that the answers would matter.
Outside of the two big relationships in my life there was the first woman I ever said I love you to. I wondered what I did to cause her to break contact and never speak to me again. But I don’t have to ask because several years ago she did contact me and we spoke for many hours. Cleared a bunch of things up. Turns out it was only about 10% me and 90% family issues I never had anything to do with.
I suspect you are not my ex, but nice story. 
“Will you please excuse me?” and then I leave.
10 years post-divorce, I still get physically ill when I have to be near her. I’ve put the badness behind me and don’t hold any grudges. It’s just an involuntary anxiety response. PTSD, I guess.
Ignorance is bliss and some things are better left unsaid, I have two kids with an ex-wife and I could ask her all these things but I prefer to let sleeping dogs lie. We got divorced last year, she wanted it and I never tried to make her stay. I’m kind of in a weird situation right now, probably not a healthy one, we are basically “fornication buddies” and I spend the night at her house a lot of the time.
The way I see it I get to be around my kids more and I still get some sexual release with a familiar partner. I don’t love her anymore and I don’t think she loves me either but we do have sexual chemistry and we can get along ok now that we don’t live together. Obviously it won’t go on forever and it kind of holds me back from pursuing a real relationship but it’s ok for now, I’ve read it’s actually not that uncommon after a divorce at least for a couple years after.
Do you know the meaning of the word narcissist?
I tried to avoid this trap by taking the advice of friends and becoming a manwhore for a while. Started with a friend who was in a similar situation, also freshly single. Yeah…we got married like 5 months later.
I can’t think of a single thing that would be helpful. At one time I would have liked to know why we broke up, but the simple reason is that she didn’t like me well enough to continue a relationship with me. How would hearing her say that to my face help?
It’s not like I’m going to hear something that would make me feel better about getting dumped. No matter what she said it would boil down to “I didn’t enjoy our relationship enough to continue it”.
Why didn’t you just tell me that it was over, instead of treating me like shit for a few months, and then telling me it was over?
Depends on the ex. One I would ask ‘why?’, another I’d ask ‘what is the airspeed of an unladen swallow?’, and to another, no questions, just an apology.
As long as you are reasonably sure (after some serious thought) that you’re not fooling yourself about potential disadvantages to this, then if it works for you…
Did you ever find my coin collection?
“Why didn’t you have the courtesy to say goodbye?”
The last time we were together was the best time. The next day I left a message on his machine. Didn’t hear from him, so left another message. Nothing. We didn’t have a fight or even a disagreement. It was just over.
He’s dead now anyway.
After all these years, are you ready to admit you were wrong about breaking up with me?
If I imagined I could possibly get even one honest answer there are a few questions I might ask. That’s a very big “if”.
When I think of it I mostly just regret ignoring my old best friend’s direct question when I told him (the friend) about her (the eventual ex-wife). His question was, “Have you lost your mind?”
I miss my friend, who died a few years ago. I don’t miss her.
I have idly wondered from time to time if I was as big an asshole 35-ish years ago as I remember, and whether there was anything redeeming about me, but I don’t actually want to know.
I could ask my teenage sweetheart why she lied to me (and said a bunch of other thinly disguised vile stuff behind a thin veneer of false virtue) about writing and singing a song about me. And not just any song, but one where she not only peered into my darkness and despair (I was crying in bed one morning, and she came to rouse me out-crying about her, in point of fact), but also told me how to overcome it all. Directions I subsequently followed, to the letter, in the interim years.
But, since no coherent logical answer is possible, I know it would be a waste of time to ask (as someone intimated upthread, it would come out as gibberish, no matter how strictly/narrowly the genie in question would enforce any truth clause). I could instead ask what the hell caused her to change so much, but, again, she probably would be unable to grasp why and then tell me.
Well I see that “What the hell were you thinking” has been covered so I’d go with “How’s your mom?” - she was a very nice lady if I was asking my college sweetheart.
I would ask my first true love(I thought) why did he have to go and die on my effing birthday. About 6 years ago his Mom saw me in a parking lot (she loved me) and told me he was sick. I found out he was under hospice care the month before my birthday. Yep, he died on my birthday. He was always vindictive. The idiot.
Most of my exs remained friends and even with the few who didn’t the various questions I had got answered over the years. But one girlfriend I had in the carefree days of my youth died suddenly; I was actually near her when it happened. I would like to ask her all the regular questions about “did I mean as much to you as you did to me” and all that but mostly I would like to know if she knows I still remember her fondly all these years later. Without starting the whole religious debate in the wrong place, that is maybe the one question I have if there ever comes a time when all things are revealed. 
(She had a dentist appointment I took her to and stroked out in the chair as far as anyone knows. I was in the waiting room and had to go and notify her mother; one of the many reasons dentists still frighten me to this day.)