If You Must Know Details From A Man's Past, Ask These 4 Non-Jealous Questions

How to get enough information without prying.

Last updated on May 13, 2025

details from man's past ask non-jealous questions Remy_Loz | Unsplash
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Find out the details about his marriages and romances that didn't work out, and you'll get a good idea of whether or not he's relationship worthy, right?

Wrong. I've been married to my wonderful husband for about 8 years, and we've spent a total of maybe three hours talking about his past marriages, and that's just the way I want it. Yet, the American Psychological Association showed "the important role of self-disclosure in the initiation process to help reduce uncertainty and allows rapport and trust to develop." 

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So, how do you dig into his past without overstepping?

Here are 4 questions to ask about his ex without looking jealous:

1. 'What are some things you learned from your ex?'

A relationship is a "thing." These are three separate entities: him, his ex, and the relationship.

In the spirit of discovering what this man is made of and how he might fit into your life, you want to learn about him, not the relationship, and certainly not her. Wouldn't it help you the most to know how his relationships formed who he is today? 

  • What did he learn? 
  • How did it make him a better person? 
  • What will he use from his past to make his future (potentially with you) brighter and better?

Knowing his ex drank too much, how they grew apart, or if he was unhappy for 5 years before finally divorcing gives you little insight into who he is today. My husband's first marriage was when he was 19. If I were judged on what I did at that age, I doubt anyone would even want to be my friend.

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You can learn these things about him by asking questions like:

  • What are some things you learned from your exes?
  • What were the positive aspects?
  • How does having been in that relationship make you who you are today?
  • What will you do differently?

Do you see the difference? No war stories, just learning more about him.

Men think before they talk. Many women process verbally, but most men don't. So, when you ask these types of questions, give him time to think before he answers. Ask the question, then be quiet. Silence is OK; in fact, men value it.

It's not a good sign if, after thinking about it, there's nothing positive he can say, or doesn't have a clue as to what he got out of the relationship. Red flag!

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RELATED: 11 Teeny Red Flags That Immediately Make You Not Want To Be Friends With Someone

2. 'One important thing I gained from my last relationship was..." and "How about you?" 

gained from past relationships details man's past non jealous questions PeopleImages.com - Yuri A via Shutterstock

Modeling the question in this way can help him get started. Don't finish that sentence with something like, "I'll never trust a man again." Set a positive, open tone that lets him know what you've learned and how you've grown. And by the way, if your answer is the trust thing, you shouldn't be dating or in a relationship yet.

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Tell the truth, but be sure to share the positive outcome that affects who you are today. This is a perfect opportunity to get in some of your nuggets about what kind of mate you want to be and what kind of relationship you value. Nuggets are magical pieces of information that help men get to know you in a remarkable way.

Think carefully about how you want to express yourself honestly and be prepared to share. When you open up this topic, it's a fantastic opportunity to dig deep and get to know very meaningful facets of each other's personality, lifestyle preferences, and problem-solving.

RELATED: I Played The Field For 30 Years. It Changed My Attitude Toward Dating: 'Don't Expect Men To Act Like Women'

3. 'How did that experience affect your dating life now?'

You need to know how to manage conversations with men. This is a powerful skill. When you do this, you can stop this from turning into a "let’s bash our exes" session. I know it's tempting, especially if you have common stories such as being cheated on or exes with substance abuse issues. Check yourself and him to keep the conversation positive and about yourselves, not your exes or the relationship.

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If you find the conversation going there, you can redirect with something like "When it was finally over, what did you learn from the experience?" or "How did that experience affect your dating life now?" If he can't see anything positive or if he keeps talking about "them" after you redirect, that is a clue he hasn't moved on. So, you should.

RELATED: 3 Secrets For Getting Over That Guy You Can't Stop Thinking About (And Finding Someone Better)

4. 'Do you want to talk about it? If not, it's OK'

There are things about my past relationships I've never shared with my husband (and vice-versa, I'm sure) and probably never will. We are both OK with that. Sometimes, what happened in the past should just stay there. Here we are in our 40s, 50s, 60s, and beyond. Do we need to know about the mistakes we made 30 years ago? I think not.

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It's perfectly wise to want to know as much as you can about a man to decide whether he is a good mate for you. But the time for this deeper discussion has to be right, and it's not on the first date.

When the time is right to learn more, keep your questions about him, and keep your comments about you. As long as neither one of you goes down the TMI rabbit hole, this conversation will be a positive turning point in your relationship, one way or another.

RELATED: Psychology Says If You Can Master These 3 Conversational Skills, You'll Always Get A Second Date

Bobbi Palmer, founder of Date Like A Grownup, is an internationally recognized expert helping women over 40 find grownup, lasting, passionate love with the right man.

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