15 Best Questions to Ask Your New Boyfriend

There are a few questions to ask a new boyfriend to have a clear picture of where things stand before you go into a serious relationship with him. Even if he is constantly buying you gifts and all the good things you have ever dreamed of, there is more to that.

If you don’t ask these questions, it can take years to get to know the other side of your boyfriend. I’m sure you don’t want to spend several years in a relationship before finding out your boyfriend doesn’t share the same goals as you or doesn’t agree with you on some important issues. 

In this article, I’ll open up to you, some questions to ask someone you like and have probably given your heart to.  You can use these questions to start a deep conversation with your man, which will give you clarity on who you’re dating. That’s not all…

Asking these questions helps to have discussions that strengthen your relationship with each other. Because you’ll never run out of what to say whenever you meet physically and they are also questions to ask him over text.

Here are some questions to ask a new boyfriend to know him on a truly intimate level…

1. Your first love was who, and why did it end?

Want questions to start a conversation? You can start from here. If you are not his first love, then this is an appropriate question to ask. You can learn more about your boyfriend’s dating past by asking him just this question. 

You can tell by his response what he values in a relationship and what actions upset him the most. And the answers can help you avoid doing things that could lead to conflict in your relationship. It also reveals how he interacts with his partners and what to anticipate if improvements are not made.

2. What are the two most important things you’ve learned from your past relationships? 

He has had partners in the past. And since you may learn a lot from hearing about those relationships, it’s worthwhile. Therefore, don’t be jealous of this one. 

His past relationships might tell you a lot about what he expects from you. Additionally, you can learn what to expect from him and how he behaves when things go wrong.

3. Where would you reside if money were not an issue?

An excellent way to determine how well you two fit. It’s a positive sign if both of you desire to reside in the same area. However, it doesn’t seem well if he prefers to live in a rural, chilly location while you choose to live in a city, warm one. If you intend to stay together for a long time, it’s important to know this.

4. Who among those you’ve known was the most toxic?

Everyone has encountered individuals who worsen the environment in which they live. You can see the worst of the worst in people, according to your lover.

Possibly, you and he dislike the same toxic trait he spoke about. In either case, you’ll discover the behaviors he hates.

5. What are some things that you probably ought to do but never will?

Many responses can be given to this slightly strange question. He has probably never been asked this, making it one of the great questions to start a conversation. But whatever his response, it will probably be fascinating and enlightening.

6. What plans do you have?

The very worst thing that can happen to a young girl is to date a guy who has no ambitions or dreams. One of the insightful questions to ask your partner is whether or not he has goals or a future that he is pursuing.  

It allows you to learn about his goals and the timeframe he has set for achieving them. This will enable you to assess how he intends to use his present means of support to realize his goals and dreams. He’s going to see you as a valuable woman whom he needs. So, it’s a way to build a romantic relationship that lasts longer.

7. What did your parents do that you thought was the best?

It can be a difficult subject at times, but learning about someone’s upbringing can reveal a lot about them.

Just keep in mind to never criticize family and to always let him do the talking. If you make negative remarks about someone’s family, people quickly become angry.

8. What distinguishes you from the majority of people?

Here is an excellent question to ask your boyfriend. And it’s also one of the great questions to ask a crush over text that will reveal their level of social integration. 

They might feel isolated if they bring up a lot of topics. They may believe they fit into society very well if they don’t have much to say. Both are OK, but it’s still useful to know.

Read more on 15 Questions to Ask a Crush Boy

9. How do you react when you fail?

Failure is a necessary part of a man’s development, but the key to that development is how he bounces back from failure. His response to the question will reveal more about his personality, including if he is target-driven or cautious about accomplishing his targets.

10. What do you think about having sex in committed relationships?

It is wise to ask this question if you intend to date your partner for a very long time. For different people, having a healthy, rewarding sexual relationship can mean very different things. 

Ensure that you are speaking the same language. If you’re someone who likes to enjoy good quality sex once a week maybe you shouldn’t be with a partner who demands sex three times a day.

11. Can you handle a woman with a career?

This question aims to find out where you stand in your new relationship as a career woman. His response lets you know whether the relationship will harm your personal life goals or not. Some men still adhere to the outdated belief that it is the man’s responsibility to support his family and that women should be fully housewives.

12. What is the one thing you want to be remembered for?

Here is one of those questions you ask in the early days of your relationship. It helps you discuss your underlying values. You’ll find out how your partner defines themselves and how they see themselves.

13. When you first saw me, what impression did you have about me?

This question reveals the attraction he felt for you when he first met you. By discussing this, you can understand what drew them to you and do your best to keep it. Most of the time, if you lose that attraction, you completely lose the man.

14. Do you see yourself with me as your partner in the future?

The crucial question about your future together exposes what he thinks. Don’t forget that you are asking him a significant question! … Therefore, don’t be offended if he pauses or responds, “I’m not sure.” He may be trying to check if you’re the woman he has always wanted. But if the response continues, then you can start to reconsider your future together.

15. What should we do to improve our relationship?

This question helps you understand how your spouse feels in the relationship, including whether they are worn out, unhappy, or trapped. Before continuing, you should voice your view about this and not just leave it to your lover. To ensure a happy relationship, this question should be chosen at random.

In Conclusion

Those are the questions to ask a new boyfriend. If you intend to remain with someone for the long term or are moving in that direction, make sure you have the same values and goals.

Use those questions to start a deep conversation. The discussions are essential to ensure that you don’t settle down with someone who isn’t right for you.

Pay attention to his answers to those questions and don’t overlook any red flags in your relationship. And discuss with him certain things you discovered and how you can sustain your relationship.

If you discover that more frequently than not, his responses do not line up with yours, you might want to quit. Of course, when someone is very important to you, there are always ways to make a compromise.

You might want to read: 15 things not to do when you start a new relationship.