The 5 Questions to Ask a New Boyfriend

This article is an excerpt from the Shortform book guide to "Act Like A Lady Think Like A Man" by Steve Harvey. Shortform has the world's best summaries and analyses of books you should be reading.

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Are you in a developing or new relationship? Are you unsure if your man has long-term goals for your relationship? What are the most important questions to ask a new boyfriend?

According to Steve Harvey in his book Act Like a Lady, Think Like a Man, there are five questions you should ask a new boyfriend. Although it may seem awkward, it’s better to know what a guy’s plans and ideals are upfront before the relationship gets too serious.

Continue on to know what Steve Harvey’s five questions you should ask a new boyfriend are.

Five Questions to Ask In a New Relationship

Have you ever discovered months or years into a relationship that your man has no intentions for you? You felt terrible, used, and like you wasted precious time. But you could have avoided that scenario if you’d known these five questions to ask a new boyfriend. Many men will string women along for the simple reason that they can. When you don’t ask a man to clarify his plans and ideals upfront, he’s not going to see a reason to offer them up himself. You have every right to know who this man is and what he wants from life, so don’t be afraid to ask.

The problem is that you are afraid to ask. You think that if you push a man to answer these important questions, he’s going to run the other way. But when it comes to your heart and time, that’s a risk you have to take. Besides, if he runs away, you know he’s not your man. 

Question 1: What Are Your Plans for the Near Future?

Your man will have a plan for the short term if he is trying to become a mature and successful man. You know what three things are important for him to feel focused and ready for love. So if you’re ready to start something real with your man, you need to know where he’s at in attaining those three things. 

Your goal isn’t to force him to choose a future. Your goal is to find out if he has one and whether you fit into it. A man who has a plan will have no problem answering. Men love to talk about themselves because they want to impress you. 

If your man has a short-term goal, ask follow-up questions. Be enthusiastic about his answers, and dig deeper to show you care and to get a sense of how serious he is. If he articulates his goals with specifics, like actions he’s taking or will take to achieve them, you know he’s working hard to become the man he wants to be. But if he has no idea about how to reach his goals, he’s a dreamer with no motivation. He’s not ready to get serious about you if he’s not getting serious about himself. 

Question 2: What Are Your Plans for the Distant Future?

A man with a short-term goal and a plan is someone who knows what he wants and how to get it. A man with a long-term plan for his life is a serious man with foresight and passion. This type of man will know whether a relationship is part of his future or not, and by asking the question, so will you. 

If his future goals are the same as his short-term goals, move on. He is driven for now, but he’s not clear about how to design a real life around his goals. You want a man who can commit to his own future because he’ll be more able to commit to a future with you. 

These first two questions push past the facade every man puts on when they meet a woman. You will know exactly the type of man you’re dealing with, and you can make informed decisions about whether you want to be part of his life and what role you could play. 

Question 3: What Relationships Are Important to You?

You want to know what relationships beyond intimate ones are important to him, including those with family, children, and God. The answers for each branch will expose a little bit more about him so you can get a clear picture of who he is and what he’s capable of. These questions should come early in the courtship, maybe even before the first date. 

You may feel like these questions are intrusive, but what else do you do when you meet someone except talk? And what are you supposed to talk about? The weather? Sports? You’ll feel anxious about asking personal questions, but get over it. You have a right to know what a man values so you can tell whether you value the same things. 

Start with family. How important is family to him? Does he want to start one of his own? If you want a family, and he doesn’t, walk away. No matter how much a man may grow to love you, his views on children are not likely to change. 

Next, find out about his relationship with his mother. If he loves and respects his mother, he likely knows how to love and respect a woman. Then, find out about his father. Do they have a good relationship? And if his father wasn’t around, did someone else show him how to be a good man? You may think that circumstances are important to consider, but how a man was raised and how he thinks about the people who raised him say a lot about his character

Finally, find out what his belief system is. If he believes in God and you do too, there’s hope for the relationship. If he doesn’t believe in God but has other beliefs that guide his values, that may still work. Even if you’re not religious, chances are you believe in something. Everyone needs something that supports their moral compass. If a man doesn’t have this belief in his life, what rules does he live by? What’s to stop him from acting inappropriately or cruelly to you? 

Once you have the answers to these questions, it’s time to move on to the last two, which are about you. The first three questions should come early, but the last two will require some time for your man to provide honest answers. 

Question 4: What Are Your Thoughts About Who I Am?

You will know right away whether a man thinks you’re a sports fish or a keeper from how he responds to this question. Give him a handful of dates to get to know you so he can’t fall back on, “I’m still getting to know you.” And although you may feel silly asking for his opinion of you, you have a right to know whether he considers you as relationship material. 

The reason this question is so effective is that it forces your man to acknowledge what has kept him coming back after that initial attraction. If you’ve kept your cookie up to this point, he may still just be trying to sleep with you. But if he’s interested in more than sex, he’ll have noticed aspects of your behavior and thought about what they say about you. 

Be prepared for a list of platitudes off the bat. He’ll tell you you’re smart and kind, a good friend, or a good mom. Dig for details. What was it that made him think you’re smart? Why does he think you’re a good friend? What did you do that gave him the impression you’re kind? If he can provide details, he’s thought about you as a real person. If not, he hasn’t moved beyond the surface to what really makes you tick, which means he probably thinks you’re a sports fish. 

Specifics equal intention. He’s been making mental notes about what he likes about you, and he wouldn’t do this for someone he doesn’t believe he can care about. 

Question 5: What Are Your Feelings for Me?

Don’t be fooled into believing that what a man thinks about you also covers how he feels about you. Thinking and feeling are very different. Again, this question comes after several dates because if you’ve been out with a man for more than a month, he should have some clue about what he feels for you. If he doesn’t, move on. 

This question will be the hardest one to answer. Men don’t like to expose their emotions or feel vulnerable. He will deflect and possibly become uncomfortable. This is normal. It’s what happens afterward that counts. If he hems and haws and refuses to answer or can’t settle down enough to attempt to be real, he’s not a man serious about commitment or you. If he shows discomfort but makes a valid effort to respond, you know you’re important to him because he’s putting himself through his idea of hell for you. 

Listen closely to what he says. “I feel good around you” or “I always laugh when I’m with you” are nice things to hear, but they’re too general. If he says, “I always feel like texting you when something good or funny happens,” you know he’s thinking about you when you’re not there and likely missing you. If he says, “You always seem to make me feel good about myself, even if I’ve had a terrible day,” you know he’s considering how his life is different with you, and this may lead him to think about what that life would be like with you in it for good.

His answers need to make you feel amazing because of who you are specifically. He might not love you yet, but if he sees how his day-to-day life is affected by your presence, you know his feelings are real and capable of becoming more. 

The 5 Questions to Ask a New Boyfriend

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Here's what you'll find in our full Act Like A Lady Think Like A Man summary:

  • How to navigate the adult dating scene
  • What men need, how they think, and how they behave when it comes to relationships
  • How women can gain an advantage and find the right man to fulfill their desires

Hannah Aster

Hannah graduated summa cum laude with a degree in English and double minors in Professional Writing and Creative Writing. She grew up reading books like Harry Potter and His Dark Materials and has always carried a passion for fiction. However, Hannah transitioned to non-fiction writing when she started her travel website in 2018 and now enjoys sharing travel guides and trying to inspire others to see the world.

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