Have you ever had an experience where you look back and wish you could have done things differently? Perhaps it was a missed opportunity, or something you wish you had spoken up for.

I am certain we all have had an experience like that at one time or another.

In my own life, I find myself asking this question in my relationships with men, both dating and when I was married.

Growing up I did not have much experience with boys or dating. In many ways, I was very naive and insecure. I understood dating as a time where you get to know the other person and spending quality time together. Included in that would be asking questions, listening, and learning to be vulnerable and authentic.

When I was dating my former husband, I missed a lot of red flags. But particularly, there were certain questions I did not ask but I wish I had asked: questions about sexuality, addiction, and problematic sexual behaviors.

We live in a culture that is sexually broken and wounded. There are so many unhealthy, destructive attitudes about sexuality that hurt both men and women. These attitudes affect how men and women relate to each other, especially in serious relationships.

As a woman whose marriage was deeply impacted by sexual addiction and pornography, I want to encourage other women to ask men they date (or are thinking about marrying) the questions I wish I had asked before getting married.

I am convinced women today need to be brave to open up these difficult conversations with men they are in serious relationships with.

The following questions are a list I actually created with my own counselor. They include:

  1. What was your first sexual experience?
  2. When were you first exposed to pornography and masturbation? What is your history with these behaviors?
  3. In the last year, how often have you watched pornography / times a week or month? What are your favorite kinds to watch?
  4. In the last year, how often have you masturbated/ times a week or month?
  5. Have you ever been to a strip club?
  6. Have you ever forced a woman to do something sexually she didn’t want to do?
  7. Have you ever propositioned a woman for sex / paid for a prostitute?
  8. Have you ever lied about the nature of your addiction? (If it sounds like he has addictive behaviors)
  9. If yes, what are you doing for recovery? What are you willing to do to be healthy?


In the aftermath of my divorce and part of my healing work, I worked to create this list of questions. I promised myself I would ask these questions and discuss them with any man before I entered a serious dating relationship ever again. These questions were based on what I was not willing to put up with in what I wanted in a healthy relationship.

And I have kept that promise. I have asked these questions to the man I have recently started dating.

It was not easy. I was so anxious and scared but I knew I had to ask these questions to protect myself. I was so afraid of the answers I may hear but I knew I couldn’t allow myself to settle on this. I was not willing to be lied to or mistreated again.

I knew I had to ask these questions to protect myself. I was so afraid of the answers I may hear but I knew I couldn’t allow myself to settle on this. I was not willing to be lied to or mistreated again.

We women need to be brave and lead in asking these questions. Regardless of the fact if your life has not been affected by pornography or not, the majority of men today have been impacted by it on some level.

Knowledge is power and this knowledge for women early on can help them discern and decide if this is a healthy relationship to stay in or maybe it is best to take some time apart for healing and sobriety to happen.

It sounds silly looking back and I feel a little bit embarrassed admitting it to you now. No one told me I needed to ask these questions.

I know it sounds crazy.

For whatever reason I did not have these conversations and I wish I had.

But now I know more.

I am stronger, healthier, and more whole than at any other time in my life.

I am taking the knowledge from my own recovery and healing journey to encourage other women to ask these difficult questions. Will it be messy and probably pretty awkward? Of course it will!

But you need to know these answers if you seriously dating or thinking about marrying a man.

Is this impossible to do? No, but it may be difficult.

No matter the answers you receive upon asking these questions it gives you knowledge with which to make the best decisions for yourself moving forward.

Have you ever discussed these questions with your boyfriend, fiance, or husband?

Are there other important questions you think that also need to be discussed?

Patty Breen

Patty Breen has been working in lay ministry for over ten years and writes online for various publications including Verily, Blessed is She, and Catholic Match. A Midwestern girl from the Mitten state, Patty finds joy in running, strong cups of coffee, Ignatian spirituality, and writing. Having gone through a divorce as a young Catholic, Patty has a heart for speaking to and supporting divorced Catholics and women dealing with sexual addiction in their dating relationships. She is passionate about messy conversations at the intersection of faith, culture, and ministry.

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