Updated on November 7, 2022

18 Questions to Ask a Divorced Man Before Dating Him

If you're thinking about dating a divorced or a separated man, there are a few things you need to know first. Divorce can be a difficult time for all people involved, and the last thing you want is to start something with someone who is still going through it.

Whether if it is over or not, there are some things that you will need to know. When talking to a divorced man your questions should be different than with a typical online dating chat.

In this blog post, we will discuss 18 questions that you need to ask before getting involved with a divorced man. By asking these questions, you will get a better understanding of what he is going through and whether or not he is ready to move on. 

1. Do You Want To Get Married Again?

Asking him this question will give you a better understanding of what he is looking for in a relationship. If he isn't sure or doesn't want to get married again, it's important to know that upfront. If he is hesitant to answer, it may be a sign that he isn't ready to move on from his previous marriage and find a new life-partner. 

2. Do You Have Kids?

If he does have children, it's important to know how involved he is in their lives. If he has primary custody, it means he will have less time for you. If he doesn't have custody, it's important to know how much contact he has with them and whether or not they get along.

3. What Was The Reason For The Divorce?

It's important to know the reasons behind the divorce so that you can understand where he is coming from. If it was an amicable divorce, then it's likely that he is in a better place emotionally than someone who went through. 

4. What Went Wrong In Your Marriage?

This is an important question to ask so that you can understand his mindset and why he got divorced in the first place. It will also give you insight into his relationships and how he handles conflict. 

5. Have You Gotten Over Your Ex Yet?

It's important to make sure that he has moved on from his ex before getting involved with him. Otherwise, there is a chance that he is still hung up on her and not ready to move on. 

6. Do You Hold Any Resentment Towards Your Ex?

If he is still angry at his ex, it's a sign that he hasn't healed from the divorce yet. This can be a red flag that he is not ready to date again. 

7. Are You Financially Stable?

Divorce can be expensive, so it's important to make sure that he is in a good place financially before getting involved with him. Otherwise, you could end up helping him pay off his debts or even worse, having to support him financially. 

8. Do You Have Any Emotional Baggage From Your Previous Marriage?

It's important to know if he has any emotional baggage from his previous marriage. If he does, it's a sign that he hasn't healed from the divorce yet. This can be a red flag that he is not ready to date again. Obviously, you should phrase it differently and not use the word "baggage" but I think you understand what it means. 

9. Are You Ready to Date Again?

This is an important question to ask yourself as well. Make sure you are in a good place emotionally before getting involved with someone going through a divorce. Otherwise, you could end up getting hurt in the process. 

10. What Are Your Dating Expectations?

It's important to know what he is looking for in a relationship so that you can decide if it's something that you're interested in as well. If he is looking for something serious and you're not, then it's probably not worth getting involved. 

11. How Much Time has Passed?

Time heals all wounds, but sometimes it takes longer than we think. If he has only been divorced for a year or two, then it's possible that he is still working through some things. If it's been 5 years or more, then he is likely in a better place emotionally and is ready to move on.

12. How Was Your Relationship With Your Ex?

If he had a good relationship with his ex, it's a sign that he is capable of having a healthy relationship. If the divorce was bitter and there is still bad blood between them, it's a red flag that he might not be ready to date again. 

13. Have You Been Hurt In The Past?

It's important to know if he has been hurt in the past so that you can be sensitive to his needs. If he has, it's possible that he is guarded and might not be ready to open up emotionally.

14. What Are Your Deal-Breakers?

It's important to know what your deal-breakers are before getting involved with someone who is going through a divorce. Otherwise, you could end up getting hurt or disappointed if things don't work out the way you wanted them to. 

15. Do You Want More kids?

Some divorced men might have kids already. Whether you have kids or not, is he willing to have more? If you want kids and he doesn't, then it's probably not going to work out.

 16. Who Decided to End the Marriage?

Asking him who wanted to end the marriage can give you some insight into his mindset. If he is the one who wanted to get divorced, it's a sign that he is ready to move on. However, if his ex was the one who ended things, it's possible that he is still hoping to reconcile with her. That could get pretty messy for you.

17. Do You Still talk to/Associate With Your ex?

If he still talks to his ex, it could be for a variety of reasons. The main one if if they share custody of their children. If they don't have kids, and they still talk, you should find out if they have decided to remain friends. If that is the case, are you going to be prepared to deal with that?

18. What are you Looking For?

When a divorced man signs up for a dating site, some might just be looking for a fling. If you're down with that, then more power to you. However, if you are looking for a relationship, be sure to flat out ask him what he's looking for. An open-ended question like this is going to reveal a lot. So be sure you ask it exactly this way to get an honest answer.

Conclusion

These are just a few questions to ask yourself before dating a divorced man. 

Obviously, you'll want to tailor the questions to fit your own situation and relationship goals. But these should give you a good starting point.

Divorced men have been through a lot, so just be straightforward in asking him these questions. It's a whole lot easier to ask behind a computer or phone when you're dating online so just go ahead and do it!

He will probably appreciated your straightforwardness. 🙂

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