Ask These Questions Before Your Relationship With Him Gets Serious

Updated April 25, 2024by Regain Editorial Team

In the early days of a relationship, partners exchange enormous amounts of information. Early love drives a desire to be near the person and to be intimate with them. Chemicals stimulate the brain's reward center, leading to intense feelings of euphoria and connection. However, this same process makes it easy to miss potential incompatibilities.

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Eight questions before you commit

Asking a potential boyfriend open-ended questions not only tells you some key details of his life, but you can also get an easy sense of how open and willing he is to communicate. Communication is essential in romantic relationships; you should expect him to answer questions honestly and openly. You don't have to interrogate him, though. Dr. John Gottman, a psychologist and relationship expert, identified eight questions you can ask to highlight areas where you may be incompatible.

What does trust mean to you?

Asking your date to explain their definition of trust gives you insight into how they structure trust and betrayal in their own mind. Trust is one of the most important components of a romantic relationship. If you and he disagree on what constitutes a betrayal, the relationship is not likely to succeed. Trust is also important to physical health; those in untrusting relationships are less healthy than those in trusting relationships.

Researchers identified four components of a trustworthy person: ability, behavioral integrity, benevolence, and value congruence. A trustworthy person can follow through on trust-promoting behaviors, behaves in a manner worthy of trust, is kind to others, and shares values similar to yours. Each person has specific criteria that fit into each category, and asking your date to openly share their vision of trust can help you determine if you and he view trust the same way.

How was conflict handled in your family growing up?

Conflict among family members is normal and common, but families differ in their approach to resolution. Knowing how your partner's family resolves conflict can tell you quite a bit about how they are likely to manage conflict themselves. If he came from a family likely to avoid conflict, he might not want to tackle problems in your relationship head-on. Conversely, if he's from a family that handles conflict through anger, he may be more likely to bring anger into your relationship.

Understanding how his family handles conflict not only gives you insight into a potential relationship but can also tell you how he will parent. If children are a goal for you, investigating conflict resolution early in the relationship can give you a sense of his approach to managing kids.

How do you feel about work now, and how do you see it changing in the future?

Asking him about his career and aspirations will tell you a lot about his goals for the future. Goal-setting is necessary for success and achievement. If he describes a plan for career advancement, he is likelier to put in the effort to achieve his goals than if he has no vision for the future.

Discussing his career can also tell you about his mindset or how strongly he believes he can achieve his goals. If he's afraid of failure or doesn't believe he can change circumstances pertaining to his career, it's less likely that he will be able to motivate himself toward his career goals.

What are your hopes and dreams when it comes to money?

Financial differences and conflicts about how money is handled are leading sources of conflict in romantic relationships. It's wise to understand how your partner intends to spend their earnings in the future. Asking him to describe his hopes and dreams tells you how he spends his money when he isn't constrained by necessary expenditures.

His financial desires should line up with yours for optimal compatibility. If you like to scrimp and save, a man with aspirations of a well-funded retirement portfolio may be appealing, while someone who dreams of buying a mega-yacht may not. Taking time to understand his feelings about money early in the relationship can save you from headaches later; financial conflict is more pervasive and difficult to resolve compared to other forms of conflict.

What does family mean to you?

Asking about his feelings about family can give you important information about how he approaches family issues. It can also tell you about his support network and help you determine how healthy his family relationships are. If he comes from a supportive family with strong bonds, he is likelier to have strong personal security and self-esteem.

You don't need to probe him too much about his family life on the first date. It's okay to learn more about specifics as time passes. Getting a sense of the big picture is important; how a person was brought up by their family impacts romantic relationships for their entire lives. You want to know early on if there are serious differences in how the two of you view family.

How did you like to play as a child?

How a person plays with others as a child forms the early foundations of how they will interact with adult peers later in life. If your potential partner describes frequent play with other peers, he is more likely to be extroverted and outgoing compared to a child who frequently plays alone. Childhood play might also give a clue to how he likes to interact with peers overall and how he approaches problems. Play is integral to childhood development, and his style of play can offer insight into his adult behaviors.

What's the most recent adventurous thing you did?

A willingness to explore and be adventurous is essential to some, while a desire to be a homebody and stick to a routine is vital to others. Discussing your date's most recent adventure will clue you into what he considers adventurous. You may also find out what he believes to be risky behavior. If his most recent adventure was skydiving or white-water rafting, he likely isn't very risk-averse. You will also learn more about the activities about which he is passionate. Shared interests help a relationship grow and succeed. If you enjoy going on adventures together, that's one more thing to bond you together.

How do you believe you have grown the most?

Asking him to define his growth offers important clues about his self-awareness, or his ability to think critically about himself and his past. A mature, self-aware person can reflect on their past mistakes and opportunities for growth and describe how their growth changed them. Growing is part of life, and the two of you will experience a lot of growth in your relationship. Knowing how he perceives and handles his personal growth process can give you insight into how the both of you will grow together over time.

How he talks about his growth can give you further information about his mindset. If he speaks as though he was responsible for his growth and was able to put in the effort to make it happen, it's likely he has a growth mindset. Someone with a growth mindset recognizes their effort and that failure and setbacks are necessary to succeed.

Trust your gut to judge his answers

It's not possible to say precisely what the "right" answer is to each of these questions. The point of asking open-ended questions like the one above is to begin a dialogue wherein you can learn more about your potential partner.

As the conversation continues, you can ask follow-up questions that are more specific to your needs and desires in a relationship. Your gut judgment is important in the getting-to-know-you process; don't ignore the feelings associated with your date's answers.

If your intuition tells you something is off, trust it. It's important to ensure you are not losing a sense of what is important to you. If you don't like a response, keep yourself open to the idea that your current date may not be the one for you. 

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How can online therapy help?

Working with a therapist online can help you sort out any concerns about how you interact with potential partners in early relationships. If you're worried you can't trust your gut judgment, suspect that your self-esteem is too low, or struggle to find compatible partners, a therapist can help. Online therapy allows you to access therapy from your home, removing barriers like traveling to an office or being restricted to therapists who practice nearby. Online therapists use the same evidence-based techniques as traditional therapists, which are just as effective when administered online.

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Talking to your new date is an important part of getting to know him, but try to use open-ended questions that invite discussion rather than interrogating him for specific pieces of information. Discussions of his financial goals, family, growth, and career will help you understand him intuitively. Trust your gut judgment when he gives his answers. If you're looking for a specific response, note it, but pay attention to how you react to his responses.

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