Polls: Dating

Let's assume, here, that it's a date, not a hookup. You're trying to get to know the person.
They're not freshly off a really bad breakup.
They're not angry and ranting.
You're not a rebound person to them.
A decent amount of time has passed since they've been in these relationships, so their emotions are not too heated, but they do have some feelings of love, pain, etc.

Now, do you want, or not want, to hear about their past relationships and people?
Does it make a difference whether it's the first date, or subsequent dates?
If you are answering yes, I assume you want to hear a bit about it, but not take up the whole date. That doesn't need to be specified.

There's no right or wrong answer here. I'm just curious, because I've heard people with strong opinions on this.

My opinion is that I want to know. It's interesting to me, and it's informative.
I would be worried, though, that if I ask, it could open up a whole can of worms, and the person might get in a certain mood, and/or it could be hard to get them off the topic, once started.
So then I have to think, is it worth the risk?
And in most cases, I would probably err on 'yes.' Except if the date was going really, really well, and we were both flirting and having a lot of fun with banter. Then I wouldn't want to talk about anything serious at all. I'd want to live in that moment, and stretch it out as long as possible, no distractions. But if the date was more serious, had more lulls in conversation, I would ask the question.

Just wondering what guys prefer

My friend told me that my ex was on an app and i found out that he used a picture I took of him where he's driving and you can hardly see him since its zoomed in and all you can see is his jacket, my jacket and my hair. You can hardly see whats going on in the picture besides his arm up driving.
*He was the one that broke up with me and told me he's not going to be on a dating site for a very long time/ if ever and he needed to work on himself.

So I have an issue...
2 guys in my life have already ended things with me based on the issue of "maturity"
My ex-boyfriend (23) and a guy I dated briefly afterward (23).

-My ex-boyfriend and I were on and off for a while b/c of his commitment issues + he was unsure of me. He would end things and come back to me multiple times because "there were things he liked about me and things he didn't like" One of the things he didn't like was that I was younger, still in school, and didn't have as much life experience
-The guy I dated briefly went out with me for 4 dates. Later on, he confessed he didn't see us dating because "maturity-wise him and I were at different spots" He even gave an example of immaturity based on my part with the first time we kissed which was was "awkward and weird"

I am a 21-year old female that works two jobs, is in college full time, is saving up for an apartment for the end of the year, and I already have my career goals in mind.
I didn't date in high school because I wanted to focus on school and I also didn't even think guys liked me + I had very low self-esteem for dating
I just started seriously dating around 2 years ago... do you think because I dated later on in life that guys that are older think I'm immature? Do I just need more experience with dating?

I feel like for a 21-year-old female, I know myself pretty well. I'm loyal, sweet, caring. supportive, open-minded, creative, have hobbies and am social
However, I can also be emotional, sensitive, shy, passive-aggressive, needy, and sometimes lazy.

Is there something wrong with me or am I just picking wrong guys? Or maybe it's both...

I do not enjoy it. Whether it's with a possible romantic relationship or platonic relationship. Usually I do all the asking. It's so annoying. I wonder if it's just me. I've me this girl who never does the asking out!!! She always gets asked.