The Secret to Learning About His Past Relationships (Without Ruining Yours)

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 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 is my opinion: The stories are meaningless.

I’ve been married to my wonderful husband for about eight years and we have spent a total of maybe three hours talking about his past marriages. And that’s just the way I want it.

MARGIE’S STORY

When we’re dating after 40, the men we’re meeting have decades of history. They can (and do) tell stories for hours! But here is my opinion:

The stories are meaningless.

I’m currently coaching a wonderful client, Margie, who is going on her third date with a new guy. Margie is 58 and widowed, her guy “Bob’ is 62 with two divorces   behind him. She likes him, but she’s dying to know more about his failed marriages.

Margie has been an ideal client. As we do the inner work of my first three steps of my 6-Step System,  as “man-shop” online together and as we carefully debrief all her dates, she takes in my information and expert advice and immediately applies it to her life…even if it’s a little scary or vastly different from what she has ever done.

So with dating Bob, Margie has followed my very important tip of not oversharing, and not letting him overshare either. She has learned to manage conversations with men quite skillfully. (Maybe that’s one reason they are on their third date? Just sayin’.)

Margie understands that the purpose of dating is to discover what you can about your guy and share what you want him to know about you. While that discovery begins from the moment you connect, it’s important to delay asking or sharing too much too soon. (Read about my “bushel basket” theory to learn why this is so important.)

Date three is generally a good time to start deciding about how you might feel with him as a long term partner. (Notice I said “start deciding.” Gathering the information you need can take time.) You want to start getting a sense of how he handles adversity, his views on relationship roles and responsibilities, his ability to communicate his needs and respond to the needs of others…you know, the stuff that makes for a solid grownup relationship.

Margie wanted to know all this and thought that getting him to talk about his divorces was how to find out. She asked me how to bring up the topic and how much could reasonably ask him.

I get this question almost every day as I’m guiding women through their dating journey. Even women who are well into a longterm relationship still want to know their guy’s story of his breakup long ago. Women want to know how to dig into men’s past, but how to do it without sounding too nosey or overstepping.

Here are my very specific guidelines to help Margie and you learn about your man’s past 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 of 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 past relationships? 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.

And here’s are a couple extra tips:

  • 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 ok…in fact men value it. ☺
  • It is not a good sign if, after thinking about it there is 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. “One important thing I learned after my marriage broke up was…..” And 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 ultimate positive that affects who you are today. “My breakup was difficult for me but I finally learned…which has helped me so much in relationships ever since.”

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. Because 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.  Do not go down the TMI rabbit hole!

I talked earlier about Margie learning how to manage conversation 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. It’s tempting, I know, especially if you have common stories such as being cheated on, or exes with substance abuse issues. Check yourself and him and 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 does that experience affect your dating life now?” If he can’t see anything positive or if, after you redirect he keeps talking about “her” 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 Larry (and vice-versa I’m sure) and probably never will. And 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 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’d be 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!

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