The 11 Most Awkward Questions To Ask A Guy When You’re On A Date

Dates are supposed to be enjoyable, right? So, most people would likely prefer that everything goes smoothly. They would probably rather not have to talk about things that make them uncomfortable. On the other hand, if you don’t learn about the other person while you’re dating, you may not have the chance to begin to build a lasting and healthy relationship. Coming up with some important questions to ask a guy on a date can be a good way to determine whether you can get along as a couple. An online profile or a quick, casual introduction probably won’t tell you all you need or want to know. In one research study, unattached subjects answered over 100 self-reported measures of preferences in a dating partner. Let’s take a look at some questions you might want to bring up the next time you’re on a date with a guy you’re interested in.

Asking questions

The real work of discovering whether you’re a good match may begin when you start dating and get to know each other better, and that may involve asking questions. With research showing that the most popular way for a couple to meet is online, getting to know the person you’re dating may happen a little faster if you’re willing to ask them questions. Asking some difficult or awkward questions can be tricky, but it can also lead to some interesting and sometimes insightful answers.

Here are some questions—awkward or not—that you might consider asking your date the next time you’re together.

1. What do you do when you fight with your girlfriend or boyfriend?

Learning how someone communicates and argues can give you insight into how they act and whether they fight fair or take an easy, mean, or aggressive way out. For example, suppose they think it’s okay to stop talking to their partner for a significant amount of time after an argument. In that case, it may be a sign that they might practice stonewalling in a serious relationship. You may want to be sure that the way they approach disagreements won’t become a toxic part of your relationship. For example, do they insult their partner, throw things, “analyze” them, or lash out at the people their partner cares about? If so, you may need to think about how they act and whether you can accept those behaviors.

2. Why did you leave your last relationship?

Sometimes, people can break up amicably and remain friends. But realistically speaking, it doesn’t happen that way very often. Asking for a breakup story can be awkward, but it can also be very enlightening. As they tell you how and why their last relationship ended, you can get a sense of your date’s preferences, priorities, and ability to resolve conflict. You might also get a glimpse into the way they manage stress and their personal life.

3. Do you want to get married?

On a date, especially a first date, it can be awkward to bring up the question of marriage. It can be a loaded question with a lot of potential for rejection. Still, it may be important to you to know whether they would even entertain the idea of marriage, you may want to bring it up when the time feels right. If you ask too soon, the answer you get may not reflect how they (or you) will feel later on down the road. You may want to ask whether they’re interested in marriage in general, but it’s probably a good idea to wait on the question of “Do you want to marry me?”

4. How do you feel about being a parent?

Taking on the duties of parenthood can be a huge commitment. If you want to have children, you may feel it’s urgent to determine whether a potential partner would even consider it. Or, if you’re worried about your age or biological clock, you may feel you need to know right away. Even if you’re young or have no children, you might want to know whether the relationship has a chance to meet your long-term goal of having a family. It can certainly be awkward but broaching the topic of where your potential partner sees themselves in the long-term in regard to having a family can be important. 

5. What is your life do you feel most grateful for?

Learning what a person appreciates in life may not only be interesting, but it might also give you an idea of what their priorities are and what they value most. Who knows? The answer might give you a chance to learn more about their family, friends, loved ones, hobbies, interests, pets, or favorite places.

6. What is your most cherished memory?

A study on relationships showed that strangers could develop closeness by asking each other 36 specific questions. One was about the memory they value the most. This question can help you learn more about a person’s background. Talking about one memory might prompt them to talk more about their experiences, what they value, and what makes them happy, potentially allowing you to get to know them in a much deeper and more personal way.

7. What things do you find attractive?

While it’s likely that you can surmise at least some of the things that your date finds attractive–you are on a date together, after all–it can help to ask upfront about what traits, features, and other things they generally like to see in others. This might include things like hobbies, aspirations, social skills, and similar factors in addition to things like appearance. Getting this information may help you learn how compatible you are with your date. It might also give you some ideas for how you can help strengthen your bond and speak each other’s love languages.

8. What would make you stop dating me?

Serious dating may be about getting to know each other well as you move toward a deeper relationship. Asking about how the relationship might end takes the opposite tack and may be awkward and uncomfortable. It might not be a bad question to ask, though. They may reveal that something about you makes them wonder if they can stay with you. They may also reveal their boundaries or limitations. For instance, maybe they wouldn’t stay with you if you started smoking or moved to another country. Or you may discover that they don’t even want to consider the question.

9. Have you ever run into any trouble with the law?

Asking your date about potential legal or criminal trouble may feel intense, but it can be another example of a way to get to know more about a person’s experiences and how they’ve learned from them. It can be important to approach topics like these with compassion and without judgment, at least if you’d like to get a genuine answer and spark a thoughtful conversation. 

10. How many people have you been intimate with in your life?

You might be in the right mindset to ask this question if your goal is to get to know your date better and you’re genuinely curious. It can also be helpful to have an open discussion about past intimate partners – was protection used? Has your partner ever been tested for STIs? Are there any experiences you may need to be aware of before entering an intimate relationship? But, if you think learning the answer to this question may make you feel jealous, it might be best to skip it and instead focus on more specific details that can help you practice safe, consensual sex (if you choose to do so).

11. Is there anything you wouldn’t tell me?

If you ask this question, they may say, “No.” After all, they may not want to appear secretive or like they’re hiding something. But getting a feel for someone’s personal boundaries can be important, both so that you’re on the same page and also so that you learn whether the two of you might be a good fit for each other.

Take the answers with a grain of salt and be prepared to answer their questions

Asking questions can be a good way to get to know someone. Of course, you may have no way of knowing how honest the answers are, especially if you haven’t been dating long enough to know them well. Remember that if you ask them questions—whether awkward or not—they may be likely to ask you the same questions or even other more difficult ones.

If you’re considering a more serious relationship with someone you’re dating, talking to a relationship therapist may be a good way to learn more about who they are and what they want out of life and relationships. Relationship counseling isn’t just for married couples. You can benefit from couple’s therapy at different times in relationships. And, if you want to examine your views, beliefs, and behaviors when it comes to dating, talking to a therapist on your own can help. Convenient, effective individual and relationship therapy with licensed mental health professionals are available online to make it even easier to get the support you may need.

Studies show that couples counseling can be beneficial for most people who choose to pursue it. In fact, researchers in one study found that a whopping 95% of couples who participated in counseling online found it to be helpful. No matter your relationship concerns, it’s likely that speaking to a licensed professional can offer you some more insight and help you form strong, healthy relationships.

Takeaway

Asking sometimes awkward or uncomfortable questions on a date can be a great way to test your growing relationship and see if it has what it takes to last. While it can be challenging to come out and ask things like the questions listed here, doing so with patience, kindness, and a genuine desire to learn can help. Being honest and open from the beginning of the relationship may be one of the best ways to help it thrive.