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10 Most Important Questions to Ask a Guy You’re Dating

These are the 10 most important relationship questions to ask a guy before you get serious about dating him. I also included a list of 13 lighter, more fun questions at the end. You’ll learn more about your date’s personality, values, beliefs and life than you know about yourself!

Don’t try to ask all these questions before dating a guy or even on the first date. The whole idea of dating is to get to know him slowly, over time! The dating process should be fun, light, interesting and creative. It takes time to really get to know a guy. Ideally, you’ll see him in a variety of situations (eg, family dinners, vacations, road trips, games nights, meeting new people) that reveal his true self.

In Questions to Ask Yourself Before Starting a New Relationship, I share seven relationship questions that you should ask yourself before and while dating a guy. It’s important to know what you’re looking for in a relationship, why, and how you hope this season of life with him unfolds. Are you looking for marriage, or a fling? Before you ask a guy relationship questions, make sure you have answered them yourself. This will help clarify what you’re looking for, why, and how you might create the relationship you want.


It’s also important to know what’s most important to you. Not your family, friends, or even your pastor or rabbi. If, for example, you really want to get married and have children but your guy is divorced and doesn’t want more kids, then you have to decide if it’s wise to date him. Do you want to start a relationship with a man who doesn’t want what you want?

Before you start dating too seriously (or fall in love), decide which relationship questions are most important to you. You might even prioritize them on a scale of 1 to 10, with 1 being “not important” and 10 being “the most important relationship question to ask before dating.”

10 Relationship Questions to Ask While Dating

Allow yourself to discover the answers over time. You might ask a question or two on each date. Try to weave them in casually, so he doesn’t feel like you’re interviewing him.

Notice if he asks you the same questions. Imagine, for instance, that you ask him where he sees himself in five years. You and he discuss his career, life and retirement plans for most of your date but he doesn’t seem interested in where you want to be in five years. Is this a guy you want to keep dating? That’s one of those relationship questions you need to ask yourself.

1. What are you looking for in a relationship?

Relationship Questions Before Dating a Guy
Relationship Questions to While Dating

It’s probably not smart to sit down and blurt out these relationship questions on your first date! Rather, look for opportunities to weave these questions into your natural conversation. It’s impossible to know in advance exactly how and when to ask a question like “What do you want in a relationship?” – but it’s important to get the answer! You’ll save yourself a lot of heartache if you know what he’s looking for. You also want to be sensitive to signs a guy is scared to fall in love and commit to one woman. Does he want to casually date you, and Michelle, and Kim, and Jennifer? That’s fine if you want to casually date him, Terence, and Larry. This is why it’s important to ask yourself these relationship questions before dating a guy you’re interested in.

2. Why did your last relationship end?

You don’t need to know all the details of the breakup or divorce, but he should be able to explain what happened in his last relationship. Be on the alert for warning signs such as: 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.

3. What are you looking for in a girlfriend?

Talk about awkward relationship questions! You may feel embarrassed to ask a guy you’re dating what he’s looking for in a girlfriend, but it’s important to get to know him. Give yourself – and him – time to learn more about each other. Be patient, and sensitive to clues that reveal what his relationship style is. Remember that the first few months of dating is the “honeymoon period” when everyone is on their best behavior. Both of you want things to go well, so you may not be completely authentic with each other. Take your time.

4. Do you have any STDs?

An even more awkward question to ask a guy you’re dating! But this is about your health. Your body is precious and should be treated with care. So is his. How he treats his body – how healthy he is – will affect your health. When you ask about STDs, tell him you’re embarrassed to ask (if you are), but you care about how healthy he is. Asking these uncomfortable relationship questions when you’re dating is how you take care of yourself in a mature, self-honoring way.

If these relationship questions are too personal to ask the guy you’re dating, read 10 Things to Talk About on a First Date With a Coworker. Those topics are lighter, but still revealing.

5. 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 you’re dating a guy with 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 information about his previous marriage.


6. Are you an introvert or an extrovert? (one of my favorite relationship questions!)

Introverts get their energy from being alone, while extroverts are jazzed up when they’re surrounded by people. One of my 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 wants to stay home and play video games. They have a good marriage, but their personality styles lead to a constant compromise about what to do on evenings and weekends. Introverts and extroverts can have great relationships, as long as they’re aware of how their personality styles affect who they are.

If you don’t know if you’re extroverted or introverted, read How to Know If You’re an Introvert or an Extrovert.

7. How do you handle conflict in a relationship?

This question isn’t as awkward, but it requires thought and self-awareness. Most of us don’t know how we handle relationship conflict. A guy (or girl) may think he likes to talk through relationship problems, but in reality he gets angry and yells when he doesn’t get his way. Which brings us back to the fact that actually dating and even being in a relationship with a guy over time is the best way to get to know him. You’ll learn how he handles conflict because it will arise naturally..

8. Are you over your last relationship?

This is a great question to ask a guy you’re dating; his answer may surprise you! Remember that it’s never easy to let go of someone you love. It’s normal and even healthy to have feelings of attachment and even love for an ex! Especially if he was married for a long time, or has children from a previous relationship. I’d be more concerned if a guy I’m dating hates or criticizes his ex that if he says he’ll always love her. We can’t just shut love off even if we’ve been betrayed or hurt.

9. Are you a spender or a saver?

Another one of my favorite relationship questions to ask while dating! Money can make or break a relationship or marriage. But, like with the introvert/extrovert relationship question, you don’t have to be on the exact same page when it comes to spending or saving money. Just be aware of his relationship with and attitude towards money. Tell him the truth about how you handle you and money and debt. When you’re dating is the best time to find out if he has credit card, student loan, or other types of financial debt.

If money is important to you, see the Financial Considerations section of my article on premarital questions for engaged couples.

10. What do you believe about God?

If you’re a Christian, date a guy who shares your beliefs. Look for someone who can help you grow forward in your relationship with Jesus and dig deeper into the power and mystery of the Holy Spirit. Spirituality is one of the most important questions to ask a guy you’re dating 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. I should’ve have put this relationship question first, because God affects every part of dating – and all relationships.

13 Lighter Relationship Questions for Dating Couples

Here’s a list of interesting questions to ask so you can learn more about his personality, hobbies, and lifestyle.

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

Phew, those are a lot of relationship questions to ask a guy you’re dating. Don’t ask them all at once, and watch what he does over what he says. His behavior and body language will tell you truths that his words can’t.

What relationship question would you add to this list? Feel free to share below!


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