4 Ways To Learn About His Exes (Without Looking Psycho)

How to satisfy your curiosity without making it weird.

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The general belief is that you learn a lot about someone by knowing their relationship history. 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?

When we're dating after 40, the men we're meeting have decades of this history. They can (and do) tell stories for hours. But here's my opinion: the stories are meaningless. 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.


But even women who are well into long-term relationships still want to know their guy's story of his past relationships and breakups. Women want to know how to dig into a man's past, but how to do it without sounding too nosey or overstepping.

Here are my very specific guidelines to help you learn about your man's ex girlfriends in a way that is respectful, yet direct, and gets you the real juicy information you need:

1. Focus on him, not his relationships.

A relationship is a "thing." These are actually three separate entities: him, her 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 out 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 that his wife drank too much, that they just grew apart or that he was unhappy for 5 years before finally divorcing gives you very little insight into who he is today. My husband's first marriage was when he was 19. If I was judged on what I did at that age, I doubt anyone would even want to be my friend.

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

  • What are some things you learned from your ex girlfriends?
  • 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. Literally, ask the question then be quiet. Silence is okay; 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!

2. Be ready to share meaningful information about yourself in a positive light.

Model for him what sharing about oneself in this way is like. For example, "One important thing I learned after my marriage broke up was..." 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, sister.

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.


Please do some careful thinking 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, problem solving skills, etc.

3. Don't go down the TMI rabbit hole.

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.

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 "her" after you redirect, that is a clue he hasn't moved on. So, you should.


4. You both have the right to keep certain things private. Forever.

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

It's perfectly wise to want to know as much as you can about a man in order to make a good decision about 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. And as long as neither one of you goes down the TMI rabbit hole, this conversation will be positive a turning point in your relationship, one way or another.

Now, can you tell me how you've been doing this in the past and how that has worked? And, how will doing it this way help you? I'd love to hear from you!

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. As a first time bride at 47, Bobbi shares her compassionate but powerful advice in her free video series "The 4 Devastating Mistakes Women in their Search for Love" at DateLikeaGrownup.com.