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Let’s discuss past relationships…

15+ Questions to ask about past relationships before getting too serious

Besides finances, a discussion on past relationships is probably the last thing anyone wants to talk about with their new boo. However, open and transparent conversations about past relationships offer significant insight into the person you are dating and may uncover red flags for you to be aware of.

In this second installment of tough questions to ask your significant other before getting married, we tackle the topic of past relationships.

Broaching this topic may cause some apprehension, but if you both are seeking a long lasting relationship, you have nothing to loose!

Ask the question…start the conversation.

But remember….even if you are really into this guy, don’t just take his words as gospel. He is telling you his perspective on his life experiences. The other actor in this play likely has a different perspective…and somewhere between the two is the truth!

So, acknowledge that if you don’t have personal experiences with his ex, any bias you may have against her is based on second-hand information.

Take the time to ask yourself the question…Would I act differently or the same way as his ex in that situation?

Be honest!

Don’t rush to judgment or worse, vilify the ex-girlfriend based on his experiences.

You haven’t walked in her pumps…so you simply don’t know what went down.

However, if you have personal knowledge that the ex is crazy, then you are at an advantage!!

Most of us, do not have the luxury of personal interactions with the ex-girlfriend or ex-wife. And even if we did, you must ask yourself whether she became ‘crazy’ because of how things unfolded in their relationship or was she always crazy??

If the latter, you should want to know what your boo was thinking when he got into the relationship… and stayed?

If the former, then you should be even more cautious!!

That’s why this discussion is so important. The list of questions below are simply primers for more in-depth conversations.

Don’t just accept a yes/no response. Your objective is to get to know your new boyfriend on a deeper level.

Perhaps the answers to these questions may help you realize whether he is the guy you want to build a future with.


15+ Questions to ask about past relationships before getting too serious


  1. Do you believe in monogamy?
  2. Have you ever cheated or been cheated on?
  3. Have you ever been in love? What was it about that relationship or that person that made you know that it was love?
  4. How does someone show you that they love you? Are you familiar with the book The 5 Love Languages ?  What’s your love language?
  5. Has your heart ever been broken? What happened?
  6. Have you ever had unprotected sex?
  7. Have you been tested for STDs, including HIV? What were the results? Are you willing to get tested again?
  8. Have you ever gotten into a physical altercation with a female? What were the events which led up to the altercation?
  9. Why did you and your ex break-up (or divorce)? If that reason was no longer an obstacle would you be together?
  10. What would your ex(es) say about you and the circumstances surrounding your breakup?
  11. Are you friends with your ex? Do you still communicate with your ex? Why?
  12. What did you learn about yourself from your last relationship?
  13. Was your ex-girlfriend/wife liked by your friends and family? Why or why not?
  14. Have you ever been physically attracted to or had sex with a man?
  15. Have you ever gotten a woman pregnant? What happened?

Let’s go into this relationship with eyes wide open!

While he answers the questions above and he recounts a particular situation with his ex, ask yourself how you would respond if you were in her shoes? When he recounts a situation with his ex and his behavior in that situation, ask yourself if his behavior was acceptable.

Was his behavior reasonable? Would you have accepted that kind of behavior?

Don’t excuse the behavior.  But remember it…store it in the back of your mind and retrieve it if necessary.

Maybe it’s a little red flag or perhaps his reaction was unique to her and he wouldn’t react that way with you.

Either way, know that at the first sign of that not-so-flattering character trait or behavior that caused you to pause, he is simply showing you who he is.

A famous Maya Angelou quote says  ….When someone shows you who they are, believe them the first time!

Therefore, you must either heed the warning signs and walk away.

Or accept the signs and continue on…with eyes wide open!

It’s your choice!

I’d love to hear how your conversations are going and whether there are any other questions I should add to the list!



  1. Those are pretty good questions, whether the person you are looking to date is either male or female. I think we frequently go blind into situations because we don’t want to know.

  2. My husband and I definitely talked about some of those before we got too serious. It’s very telling to hear the answers from him, and I’m sure he felt the same way about hearing them from me.

  3. Very important questions indeed. The awkward part of asking things though is a struggle don’t you agree? having said that, of course we should all grow up and ask what needs to be asked like you said! Thank you for sharing.

  4. Boy this is a loaded list of questions. But in today’s world they’re necessary. Might be a good idea to write a post on HOW to broach these topics in a tactful, non-interrogational way. LOL!

    1. Ola, thanks for the suggestion…I will definitely consider writing a post on the HOW TO ASK these questions. Take care.

  5. It’s so important to discuss these types of issues. If you or the other person don’t want to talk about these things then it’s not the right relationship!

  6. Yes, these are so important to ask! I met my husband in high school, so he didn’t have as much history at least. But I did ask about past relationships and such.

  7. So important to get to know of the person you wish to take relationship ahead.. It builds a sense of faith & an open relationship must for a great life!

  8. I love that Maya quote and I think in the past relationships I saw the warning signs but I still went in with eyes wide open. These are truly important questions to ask

  9. Yes! These are so important!! These questions were brought to light early in my relationship with my SO. We’ve new. Together 3 years, it’s necessary to have these questions answered

  10. I wish I had these words of advice before my first REAL relationship in college. My ex always compared me to his ex and it turned into an abusive relationship. I never even really thought to have this conversation or ask these questions! Could have saved me a lot of heartache. Great post.

  11. It is very important to share honestly with the person you want to have a relationship with, and to start conversations like this. It will promote a longer, healthier marriage!!

  12. These are pretty good questions. I am not going to be dating any guys ever in my life who refer to their ex as “crazy.” I have had too many experiences to know that a “crazy” woman has been mistreated by her partner and if HE is calling her that, then he’s the partner who caused it. So no.

  13. I believe in honesty from the get go. You never know if you will be with this person for one week or forever so why have any lies or dishonesty you may need to explain yourself out of later? Great points here.

  14. These are great suggestions for talking to a new potential mate. It’s good to think about all these before you get too far into the relationship

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