7 Awkward Questions Millennial Women Should Ask a Potential Husband

Some of these questions may seem intrusive, even outrageous. But you should have answers to all of them if you're considering marriage.

John Elliott | June 5, 2018

Some of these questions may seem intrusive, even outrageous. But you should have answers to all of them if you're considering marriage.
7 Awkward Questions Millennial Women Should Ask a Potential Husband

So, you’ve met a guy. You have dated for a couple of months and you have the feeling that this could be the one. If you are a typical millennial, then you are probably in your late twenties or early thirties. You know the clock is ticking. On the surface, your new love interest appears to be okay. He has a job, drives a nice car and pays for your meals. Maybe you’ve even spent some money on a website to see if he has a criminal record. So far, he checks out. What then do you need to know about him? 

I suggest the following seven awkward questions. You need not pose them all at the same time. But you should have answers to all of them if this man is going to be the father of your children.

1. “How much debt do you have?”

Financial pressures are one of the biggest causes of divorce. You do not want to start a marriage wondering how to pay the rent. Does he have student loans, credit card debt and car payments? You need to find out. You may not have to go as far as asking for his credit report or his 1040s. Nevertheless, this first question should provoke a healthy discussion about his earnings, spending habits and priorities.

2. “Do you have children from a previous relationship?”

If he does, then you will be married to the child, and the child’s mother, for the rest of your life.  Ex-wives can become vindictive when they see their former husbands or love interests move toward remarriage. I have watched female friends mired in lawsuits after marrying divorced men with children. In each case, the ex-wives involved had been amicable, until the new woman showed up. Children are not necessarily a deal-breaker. But you should have no illusions about what awaits you. 

3. “Do you have an STD?”

 As rude as this question might seem, it should open the door to an honest discussion about his “past”, particularly if it involved risky sexual behavior.  What did he do on that Vegas vacation?  You need to know.

4. “Do you have a  problem with drugs or alcohol?”

If the answer is yes, you walk.  Period. 

5. “Do you like my mother?”

There is a good chance your mother is your best friend.  If you have children, she will be a regular house guest. The fact is, the mother-daughter relationship is the closest one. It is very important that he gets along with your mother. Correspondingly, your mother should like him too.  In fact, your family is often a better judge of these things than you are. If they don’t like him, that is a bad sign. I once intervened to break up one of my son’s engagements after everyone in the family urged me to do something. Assuming you don’t come from the Manson Family, you’d be wise to listen to the counsel of your family.   

6. “Will you stand up to your mother?”

The mother-in-law/daughter-in-law relationship is a minefield. It’s rare that a mother becomes the BFF of the woman her son marries. Men naturally have difficulty navigating the space between the two most important women in his life. For that reason, you have to know that he will put you first and will protect you from her meddling. My own father failed to stand up to his mother in the first years of his marriage. The result was decades-long estrangement between my mother and grandmother. The Book of Genesis says, “A man shall leave his father and mother and cleave to his wife.” That is a serious command with far reaching consequences. 

7. “Will you let me be a stay-at-home mom?”

This puts the question of children front and center. It forces him to articulate a vision about the kind of family that he wants. If he does not want children and you do, then the prudent thing to do is to end the relationship. By posing this question, you are asking him to be a provider and a leader. If he does not want that role and you wish to stay at home with your children, you’d be entering a marriage fraught with difficulty. My recommendation? Don’t do it.

These questions may seem intrusive, even outrageous. But since millennials tend to marry in their late twenties and early thirties, most accumulate a lot of “history.” Previous generations married earlier. They often grew up together. They knew a lot about each other already. That is no longer the case. 


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