10 Most Important Relationship Questions to Ask a Guy

These are the most important relationship questions to ask a guy before you get serious – plus a list of fun questions that will show you his personality, hobbies, and tastes in life.

Relationship Questions to Ask a GuyIf you don’t think the guy you’re dating is for you, read Calling in “The One”: 7 Weeks to Attract the Love of Your Life. Katherine Woodward Thomas shares her own personal experience to show women that in order to find the relationship that will last a lifetime, you have to be truly open and ready to create a loving, committed, romantic union.

In Questions to Ask Yourself Before Starting a New Relationship, I share seven relationship questions that you should think about before dating a guy. These questions are the ones you should ask him – and that you should think about yourself. Hopefully, he’ll ask you for your answers to these questions after you ask him. If he doesn’t express any interest in your thoughts on these relationship questions, he may not be as into you as you hope.

Important Relationship Questions to Ask a Guy

There are no right or wrong answers to these relationship questions. If you feel like you can’t ask a guy these relationship questions, that’s your first sign it’s not a good idea to date him. Never do anything with a guy that you can’t talk about, and never start a relationship with a guy if you can’t ask him questions.

What do you want from a relationship?

Does he want to casually date you, Michelle, and Tom? That’s fine, as long as you want to casually date him, Terence, and Lasheika. Or maybe his answer to this relationship question is: I want to get married tomorrow and get you pregnant and start building a family of children. That’s fine, as long as you want the same thing out of your relationship.

Why did your last relationship end?

You don’t need to know all the dirty details of the breakup, but he should be able to explain what happened in his last relationship. Here are a few warning signals for this relationship question: he hates his ex, he has kids with his ex that he doesn’t see or support, he doesn’t know why they broke up, or he refuses to talk about his previous relationship.

Again, this is one of those relationship questions to ask a guy that you need to be able to answer yourself. If you’re still friends with your ex, read 7 Reasons You Should Not Stay Friends With Your Ex.

What are you looking for in a girlfriend?

If he can’t answer this question right away, give him time to think. This is one of those relationship questions to ask a guy that takes some thought. You don’t have to get all the answers today…give him space before you jump into a relationship with him (and do not have sex with him yet!).

Do you have any STDs?

This is one of the most awkward questions to ask a guy, but it’s also one of the most important! STDs can affect your fertility, long-term health, and future relationships. If you have STDs, you need to tell him about your health, and how your STDs might affect him.

Is your relationship in trouble?

Get 7 Steps to Fixing Your Marriage - and FREE relationship advice. No strings attached.

How often do you see your ex-wife and children?

Unfortunately, How to Deal With Your Husband’s Toxic Ex-Wife is one of my most popular articles. If your potential partner has an ex-wife and kids, you need to know how he’s getting along with them, when he sees them, and how they affect his life.

If he’s divorced, you might be able to look up his divorce file and the court proceedings in the legal system. This can give you important insights into his previous marriage – without you having to ask awkward relationship questions that make him uncomfortable.

Are you an introvert or an extrovert?

Introverts get their energy from being alone, while extroverts are jazzed up when they’re surrounded by people. One of my best friends is an extrovert who loves to be the center of attention and go to all the parties and events. She’s married to an introvert who loves to stay home and play video games. They have a good marriage, but their personality styles lead to a constant discussion of what to do every evening and weekend.

Introverts and extroverts can have great relationships – as long as they’re aware of how their personality styles affect who they are.

How do you handle conflict in a relationship?

This is another tough question to ask a guy, because he may not really know how he handles conflict. He may THINK he likes to talk through relationship problems, but in reality he gets angry and yells when he doesn’t get his way. It’s still an important relationship question to ask – and to answer for yourself.

Are you over your last relationship?

Two things come to mind about this relationship question: ask a guy, and he may lie. Also, broken hearts never completely heal. So I suspect he’ll say yes, he is completely over his last relationship…and I also suspect that he isn’t being 100% truthful. The longer and more involved the relationship, the more grieving and healing that needs to be done. If he doesn’t need to grieve or heal after his last breakup, then he’ll be carrying around emotional baggage that will affect your relationship with him.

The same goes for you! If you’re hung up on the past, read How Long to Wait Before Starting a New Relationship.

Are you a spender or a saver?

Important Relationship Questions to Ask a Guy
10 Most Important Relationship Questions to Ask a Guy

O boy, money can make or break your relationship. Just like the introvert/extrovert question to ask a guy – you don’t have to be on the exact same page when it comes to spending or saving money, but it sure makes life easier! This shouldn’t be one of the most difficult relationship questions to ask a guy, but many women feel uncomfortable asking it. Don’t be shy – ask him about his spending and saving habits.

You might even ask if he has credit card, student loan, or other types of financial debt (though these are more premarital questions for couples who are engaged than relationship questions to ask a guy you’re thinking about dating).

What do you believe about God?

If you’re a Christian, you need to hook up with a Christian guy. This is one of the most important relationship questions to ask a guy because it will affect EVERY part of your relationship. Don’t brush aside your beliefs and values because you like him or because you’re scared you’ll never be loved by anyone else.

Trust God to bring you the right guy, and to lead you towards the relationship that’s best for you. If you’ve been waiting for the right guy forever, read How to Deal With Unanswered Prayer.

Less Personal Relationship Questions to Ask a Guy

Here’s a quick list of interesting questions to ask, which will reveal his personality, hobbies, and lifestyle.

  • What is your greatest life achievement?
  • Who is your favorite person?
  • Are you a jealous person?
  • Where is your best holiday?
  • What brings you joy in life – what makes you happy?
  • How often do you drink or do drugs?
  • What did you want to be when you were a kid?
  • Do you have a favorite song, type of food, or book?
  • What’s the most expensive thing you ever bought?
  • How do you deal with change?
  • Have you ever committed a crime?
  • What was your first kiss like?
  • How would you define a good sexual relationship?

These are a lot of relationship questions to ask a guy – and I wouldn’t ask them all in one sitting or on one date! Ask one or two questions every time you see him. You might even consider texting him some of the questions, especially the less personal ones.

I welcome your thoughts on these relationship questions to ask a guy, but I can’t offer advice or counseling. If you can’t decide if you should start dating him, share your reasons below. Writing might help you figure out what’s holding you back, and how to move forward.

May God bless you and keep you safe. May your relationship be based on love and mutual respect, and may you know with all confidence that this is the right man for you.


Imagine TEXTING your way to a better relationship - or even getting your ex back! Text Chemistry: A Simple Way to Use Text Messages to Strengthen Your Relationship.

Leave a comment

Your email address will not be published. Required fields are marked *