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19 Questions to Ask Before Dating a Separated or Divorced Man

Questions to Ask Before Dating a Divorced or Separated Man

The world and its people have come out of their shells now. People are more liberal now than ever. Society today affirmatively accepts separated or divorced people. So, if you've fallen in love with a separated guy and are wondering if you made the correct move, then you must remain stress-free. It is wonderful to find your true love in someone who was once somebody else's love. It is undoubtedly an amazing feeling to be someone's first, but it feels best to be his last one.

However, while for other situations, you need not bother much about your man's past. This is a situation where you must be aware of almost every essential thing about his past relationship. Getting hitched to someone requires building a robust and trustworthy bond. And it is impossible to do that if you carry doubts inside you.

19 Important Questions to Ask When Dating a Separated or Divorced Man

You indeed have lots of questions in your mind. And you must need to clear them as well before making your relationship official. But remember that it is not only about you but him too. It might be a bit difficult for you to commit a man with a wedding history. But it is not easy either for him to trust someone again under the same commitments. Hence, while you ask your questions or consider factors, make sure you are not hurting his sentiments.

Below are some questions listed sequentially. You can follow up the list if you feel at sea.

1. Is He Comfortable Discussing His Divorce/Separation? 

Don't jump straight into the topic of divorce. Initially, inquire about his problem. If he is still undergoing the process or recovering from it, he might feel a bit uncomfortable discussing that topic. However, if he always tends to beat around the bush, then there could be some trouble you need to clarify.

2. What's the Current State of His Separation?

Generally, there are four types of separation that couples undergo. It could be trial separation, living apart, legal separation, and permanent separation. It can be he is just living apart and cheating on his wife. You must have a clear idea about your partner's separation procedure.

3. How Long has He been Separated?

If he has already been separated, ask him how long it has been since their separation. If it is long enough, then you might not have anything to worry about as such. But if it is a brand new event, then be cautious about his feelings for you and his previous relationship.

4. What are His Views on Marriage Currently?

Being in love and being responsible are two different things. Someone who has had a terrible experience, in particular, may be hesitant to repeat the same step. You can ask your man to share his views on marriage. And see how positively or negatively he takes it.

5. Is He Ready to Get Hitched Again?

Every relation requires a strong commitment to experience a smooth acceleration. It may take some time for him to reach that point in this case. But it shouldn't take too long. Some people are afraid of repeating the same venture if the prior one was a failure. Thus, get to the terms of what your man thinks about the future of this relationship.

6. Did He Want the Separation?

You need to know who initiated the divorce. It is crucial to understand if he wanted it equally as his ex. If he did, then it could be a positive sign. It might help you to assure if he is entirely out of that relationship or something is still holding him back.

7. What was the Reason behind the Divorce?

It doesn't matter how silly the matter was and who came up with the idea of divorce. You have the right to ask its root cause. The way he tried to handle it would tell you a lot about him. Also, if he was responsible for the separation, you need to analyze how healthy or valid his reason was.

8. Are They Both Still Living Together? 

He might not be yet divorced or undergoing the process, but it matters if they are still living together. If he does so and is also serious about his relationship with you, then his soon-to-be-ex must be aware of you. However, that should be the case anyway, even if they already had a divorce. But it becomes crucial while they are still somehow connected with the once taken vows.

9. What are His Feelings for His Ex?

A man's attitude towards his ex can explain a lot about his nature. If he is too rude or accuses her of being an apple of discord, then there is something you need to worry about. Also, if he is still emotionally involved with her, then it is better to give him some time. But be careful and stay aware of all the possible connections between them.

10. Does He have a Child? 

If you are dating an already married person, then this is something you must know about. You should be familiar with the members and people related to his previous marriage. If you are dating a man with kids, then there is a considerable responsibility waiting in your way. It is better to approach further only if you feel like you are ready.

11. How did He and His Ex Split their Parenting Duties?

You don't necessarily have to become the mother of his child while being his wife. You can be that kid's friend or whatever relation you feel to develop with them. Thus, it is better to have an initial idea of how the ex-couple is parenting mutually.

12. Did They Both Mutually Agree to see Other People?  

It doesn't matter if they are on the verge to divorce or are confirmed to separate. Everyone should agree with each other. Even if your guy is content with his relationship with you, his ex's acceptance is as significant. If she isn't at ease, it might lead to problems in the future, especially if they haven't divorced yet.

13. How often do they Communicate with Each Other?

It's important to stay aware of everything of how often he meets or communicates with his ex-wife. So that you don't evidence a bolt from the blue if you observe them talking someday.

14. Which Type of Relation Both of Them Choose to Continue?

It is okay to be above board with your partner. Hence, you can directly ask him for that type of relation they decided to maintain. Some people choose to stay friends even after their divorce. There is nothing wrong with it. But in case you don't feel comfortable, you must clear it out with him.

15. Are there Things He Expect to Happen Differently in this relationship?

There might be tons of things he learned from his previous marriages. You can ask him how he decides to put effort into his relationship with you. Also, how he plans to build your relationship stronger and different from the earlier one.   

16. What is His Financial Condition Currently?

You don't need to present yourself as a gold digger. But finances are a part of life that can't be ignored. Your partner might have several things to carry with him, like alimony or child expenses from his previous life. Being his would-be partner, you might also have to take part in his some or the other thing. Thus, it's better to be aware of that from the beginning.

17. Is He Emotionally Available for You?

Action speaks more than words they say. It is true in many ways. He might often say how important you are or this relationship is to him. But you need to observe if he is always there to support you emotionally and mentally.

18. Does he believe that he can spend his life with you?

It's better to know at the beginning what the person thinks about you and the relationship. If he is not looking for a long-term relationship and doesn't want to spend the rest of his life with you, you need to think before going ahead.

19. How do you feel when you are with Him?

The vibration of a person says a lot. If you feel good and safe with him, you can move to the next step; otherwise, you need to think. It would help notice his reactions to small things, whether it shows care for you or frustration with his previous experience.


A relationship needs to be honest and straightforward. It is okay to be open and ask everything you have in your mind. But make sure you don't hurt your partner's emotions in that procedure.

It doesn't matter if your man is divorced or separated. His previous relation doesn't define his nature and attitude in a marriage. However, it can be the opposite at times. And to sort that out, you can begin with considering the questions mentioned above. Then make a better decision for yourself based on your observance.