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How To Ask Him About His Past Relationships – 4 Relationship Experts Share Their Best Tips + Insights

by Kate Houston – Love Coach, Katherine Woodworth – LPC, CRC, Amy Sherman – M.A., LMHC, Michelle Henderson – MA, LMHC

How To Ask Him About His Past Relationships

“It is necessary, and even vital, to set standards for your life and the people you allow in it.”

~ Mandy Hale

Mandy Hale Standards Quote
Michelle Henderson

The past is oftentimes our greatest teacher. 

After all, all of our past experiences have led us to this current moment in time and play a role in why we make the decisions we do now. For many people, talking about the past (especially the traumatic or painful parts) can feel like re-opening a wound. 

They hesitate to do it because they don’t want it to hurt. Some people also hold a belief that the past “shouldn’t matter” and that it’s best to set our sights on the future without looking back.

When it comes to a relationship, I believe it is absolutely essential to know the nuts and bolts of someone’s past. While talking about these things can be painful and uncomfortable, moving forward into a new relationship without an understanding of the other person’s past can create an emotional divide. 

There are many things that are “optional” in terms of sharing about the past, but I would say at the bare minimum, it’s important to know the answers to the following questions:

  • How many relationships has he been in? How many sexual partners has he had?
  • Has he ever been in love? Has he ever lived with a romantic partner?
  • How long ago did his most recent relationship end? What was the reason for it ending?

The key thing to note about these questions is that some of them can be answered with a simple yes or no answer and the rest can be answered in one sentence, normally just by saying a number. You don’t need to know every single detail and many times those details will come out organically over time. 

If he seems uncomfortable opening up, try the following:

1. Tell him he doesn’t have to talk about now.

It’s crucial that this conversation happen only when both people are ready to discuss it. If he’s not ready, give him some time and re-visit it again in a couple weeks if he hasn’t come back to it. If he still refuses to talk about it then, move on to the next suggestion below.

2. Talk about why it’s uncomfortable.

Maybe he had an ex who got super upset when he was honest with her about the details of his past. Many people carry shame about their past which makes telling the truth about it very difficult. Ask if there’s anything you can do to make it feel safer for him to open up and assure him that you don’t need to know everything. When he does start to share, listen without interrupting and pay full attention to what he’s saying. It may help if you hold hands while he’s talking.

3. Lead the way.

If nothing else, try talking about your own experiences first to see if that helps him feel more comfortable with opening up. Many times, this creates a space of vulnerability for the other person to do the same.

Michelle Henderson, MA, LMHC – www.nextchapter-counseling.com

Sally LeBoy

Information about past relationships is a delicate and maybe, one could even say controversial topic

I think it’s a topic that should be brought up when a relationship seems to be getting serious.  There is value in having information about past relationships because as we all know, the past is a pretty good predictor of the future.

It might be a bad sign if your partner is secretive about past relationships

That is assuming that you are asking for the right reasons.  Sometimes people ask because they are jealous or possessive. Your insecurities are not his responsibility. Unless your feelings are coming from your relationship with him, you have to figure those out for yourself. 

Nobody needs to justify their pasts, but sometimes the information is really important

  • Has he had serious relationships or does he tend towards serial monogamy?
  • Were his relationships characterized by drug or alcohol abuse?  
  • How has he handled conflict? 
  • Was there ever any physical or emotional abuse?  
  • Did he or his former partner cheat?  

These dynamics are serious, take hard work to overcome, and could impact the quality of your relationship with him.

We all make mistakes but learning from them is the way to become better partners in the future.  Is he able to take responsibility for the part he played in past relationships that ended badly?  

It is never just one person’s fault.  Relationships are a system created by both partners.  Each partner has to take responsibility for his or her part in creating and maintaining the dynamics.

You have the right to know anything that would affect you ranging from past marriages, kids, hereditary illnesses, and struggles with any kind of abuse.  

But that’s all you’re entitled to know.  We are all entitled to privacy.  Being in love doesn’t give anyone a free pass into somebody’s past.  

Ask yourself why you are interested in the answers to the questions you want to ask.  

Is it information you really need to know?  If it is, it’s important that the questions get asked and answered. But be sensitive. Think of how you might feel answering those same questions yourself.

Sally LeBoy, MFT – www.sallyleboymft.com

Kate Houston

What is it women actually want to know when they prod for information about a man’s past relationships?

Where does this need to know come from? And how can women get the answers they actually want while also opening up, being vulnerable and creating the kind of intimacy with a man that leads him to fall in love?

First, let’s look at the why.

Why do women have a insatiable need to know all about a man’s past relationships? Usually, this sudden pull to find out comes up once women begin to emotionally invest in the man. They begin to take their hearts off the market and direct all their hopes and dreams toward one guy. They want emotional assurances that the man is a good guy and will treat her well.

The thing is, this whole process is backwards and is a disaster waiting to happen because women make a couple of key errors that start them down a path of doubt, distrust and fear instead of make decisions where they could completely empower themselves.

Women simply aren’t asking the correct questions. Nor directing these questions to the right people.

Yes, women DO deserve to be treated well, but often they want to know the excruciating details of what happened in a man’s past relationships. What he said, what she said. This information doesn’t give women the information they really want – it only propagates their fear that this guy could do that same thing to them.

Instead, when women start to feel a tug on their hearts that makes them believe they should direct all their feelings and attention onto one man, they should ask these questions:

  • Do I feel this way because I want HIM to be exclusive with me?
  • Do I ask him about his past, thinking it’s a safe way to find out how he will treat me?
  • By asking him about his past, am I looking for reasons to judge him, be critical of him or close my heart off to him?

Women who answer yes to these questions probably feel too scared to share their fears with their man and want to protect themselves from being hurt. That makes sense. But it also creates distance instead of connection with the man.

When women feel grounded and empowered in their vulnerability, they can ask for what they want and need from a man. 

That creates intimacy and connection and makes a man fall more in love.

So what DO women ask a man and why is this more important than knowing the details about his past relationships?

Be curious! Ask him what he learned from his last significant relationship. 

And then be quiet and listen. He will tell you a lot. And it will let you know who he is and how he wants to be now, in the present, and in a growing relationship.

He will tell you if he takes any responsibility for the demise of the past relationship, what he learned about himself and what he wants to experience in relationship now because of it. If he doesn’t hold himself accountable for anything and completely blames the woman for everything, then that tells you how he will treat you and the relationship. 

And it won’t be  the loving, growing partnership you desire. 

Kate Houston, Love Coach – www.rockstarlibrarian.com

Amy Sherman

It’s always hard to find out personal information about your boyfriend and you certainly don’t want to appear intrusive

So there are some guidelines to consider before you even broach the subject and many have to do with where you are in the relationship. If you feel insecure it means you do not feel confident in your abilities and have doubt or uncertainty about yourself.  It is not a good feeling to have when you are in a relationship and curious about your partner’s past history.

Examine these guidelines so you feel more in tune with your motives:

Rehashing his past, reliving negative feelings from your past, opening up long gone emotions only keeps you experiencing all those feelings that make you angry, sad, disillusioned and disappointed.  

Why go there if your new relationship shows good potential for something long term and permanent? In other words, if it’s not important to your relationship now to delve into the past, why bother? 

Trust your intuition if anything about him makes you feel uneasy; just don’t ignore it, but be sure the “messages” you are receiving make sense from a logical perspective, rather than an emotional one. Is he hiding stuff about his past because he’s evasive?  Is he being secretive and mysterious?  You have a right to know what’s going on.

Talk about his past when relevant issues come up.  

For instance, if he was married before and has a kid, you would want to know about his ex-wife and what she was like, so you can better relate to this child. Let him know your unease about his ex and why, so he can adjust his behavior appropriately – if he cares to.

Be open and clear in your communication style with your partner.

If something bothers you, can you express how you feel without ridicule or fear?  When you feel comfortable discussing your expectations, concerns, and desires, you are less likely to misinterpret your partner’s actions or behaviors and also not be disappointed in his reactions.

Your relationship is a work in progress, and as you continue to grow and learn together, your relationship needs to be based on trust, respect, ease of conversation and transparency.  

These elements leave no room for doubt, mistrust, or suspicion.  So work through your insecurity because this aspect of your character and personality will impact the success and depth of your potential relationship.

Amy Sherman, M.A., LMHC – www.yourbabyboomersnetwork.com

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