13 nice questions to ask a guy on the first date

Modified: June 23, 2023, Published: December 4, 2015

Embarking on a first date can be a thrilling experience filled with anticipation and the excitement of getting to know someone new. It’s an opportunity to create a memorable impression, establish a connection, and lay the foundation for a potential future together.

One of the keys to a successful first date is engaging in meaningful conversation that goes beyond the surface level. By asking thoughtful and interesting questions, you can create a comfortable and enjoyable atmosphere where genuine connections can be formed.

To help you make the most out of your first date, we’ve compiled a list of 13 nice questions to ask a guy. These questions are designed to spark engaging discussions and provide insight into his personality, passions, and experiences. They will help you explore a range of topics, from his hobbies and interests to his values and goals in life.

1. Who are you voting for this election?

A: Whether the guy you’re asking cares about politics or not, this question might seem boring to some. It’ll get him to think about the elections in general. No matter what his answer is, it’ll always lead to a discussion on why so. He might even ask you whom you’re voting for. Score. Maybe.

2. How would you describe yourself?

A. This one is a sure fire-starter, especially for someone whom you just met. Think of it as an interview. Even guys who don’t like talking about themselves will have to say something. It’s an easy go and one that’ll quickly let you know what this guy is really like.

3. If you could pick someone’s brain, who would it be and why?

A. There’s much to say about a person and whom he idolizes. Is it Einstein? Is it Michael Jordan? Is it President Obama? Or is it Jerry Springer? This is an interesting one to discuss, and while you’re at it, you should ask yourself the same question.

4. What is your favourite thing to eat?

A. Food is always an easy conversation. Everybody eats, after all. This question also presents plenty of exciting follow-ups. You can easily add “…after sex?” Or “…after working out?” Or “…in the movies?” Any of those will completely change the context of the question. You have to be creative.

5. What is your favourite reality TV show?

A. Most people are embarrassed to admit they indulge in reality TV. But they do. If a guy tells you he doesn’t watch reality shows, you can segue into asking what type of shows he watches. If he says he doesn’t watch TV at all, then you can ask him what he does in his free time. If he says he doesn’t do much, you should move on to the next one.

6. What do you think of the Bruce/Catelyn Jenner affair?

A. This highly publicized private matter has forced people to examine their own opinions and ideas about psychosocial issues. We’re not getting too technical, but it’s an excellent way to grasp where his head is at regarding touchy subjects such as sexuality in general and not just transgenderism.

7. What types of music do you like or currently listening to?

A. Music, they say, is the language of the soul. It allows people to connect on a different level. It’ll be interesting to see what his tastes are like and if you care about them at all. If he says he doesn’t like music, you can maybe even open his eyes to a great new world. If it turns out that you don’t like music either, then you’ve just met your match.

8. What is it like at your work?

A. This is a carefully put the question, as some people don’t like to talk about work outside of work. Some people do, though, so this question gets the best of both worlds. This is one of those questions you should genuinely be interested in asking, otherwise don’t. The answer could be long-winded in some cases. The guy might give you a minute-to-minute guide on what goes on in his day. Or he might tell you that his work is fine. Either way, it’s good to know what a guy thinks about his job.

9. What is your most remembered childhood memory?

A. Realize that you aren’t asking for a “favorite” memory but rather the “most remembered” one. This question has the potential to get soft, so favourites have been replaced. Some childhood memories are not the best, and these might be the ones that’ll get you inside the workings of his brain.

10. What is your biggest regret in life so far?

A. They say everybody’s got regrets in life, though some people claim to say they don’t. Either way, the conversation goes, it’ll be a good one. If a guy claims he has no regrets, the conversation will go on to take the form of how he lives his life without regrets. If a guy has regrets and continues to tell you about them, then he’s probably just shared some of his most intimate secrets with you.

11. If you could be passionate about any global crisis, what would it be?

A. This question has many extra points finding clues and answers for you. The first being is if the guy knows what global crises are. If you care for somebody to know something about the world, then this matters. The second being is if he knows current affairs and if he cares. If he does care about something, what does he think about it? This question is a tad more severe than we’re used to, but it works.

12. How do you show someone you care for them?

A. Time to get all gooey now the serious stuff is over. Any guy can make out words to make this answer sound good. Your job would be to decipher the truth from the flukes. If a guy is genuinely caring, the solutions might be straightforward. Sometimes, when guys try to embellish their character, they resort to decorating their words a little. This question will be both fun and sweet if you get the correct answers.

13. What is your ultimate retirement fantasy?

A. Maybe it’s to an island getaway. Maybe it’s to have tons of money. Maybe it’s to do it as young as possible. The first important thing to know is if a guy thinks long-term. If he does, then that’s good for you. If he’s a little vague with what he wants for retirement, chances are it’s because he’s not thinking about it. And if he’s not thinking about retirement, he’s probably not saving any money, and he’s probably not as responsible as you think he is.

What to avoid asking your date?

When it comes to getting to know someone on a first date, it’s important to approach the conversation with sensitivity and respect. While you may be curious about various aspects of your date’s life, there are certain topics that should be handled with care to maintain a comfortable and enjoyable atmosphere. By being mindful of what to avoid asking, you can ensure that your date feels respected, valued, and at ease.

One area to tread lightly is discussing past relationships. While it’s natural to be curious about someone’s romantic history, delving too deeply into this topic can bring up negative emotions or create an uncomfortable dynamic. Instead, focus on the present moment and the potential connection between the two of you.

Another area to steer clear of is personal finances. Inquiring about income, debt, or financial stability can be invasive and may make your date feel uneasy. Money matters are often considered private and discussing them too early in a relationship can create tension or awkwardness.

Sensitive family issues should also be avoided during a first date. Everyone has their own family dynamics and experiences, some of which may be difficult or painful to discuss. It’s important to allow your date to open up about their family in their own time, if they feel comfortable doing so.

When it comes to politics and religion, these topics can be deeply personal and potentially divisive. Unless you have established a shared interest in discussing these matters, it’s best to steer clear of them on a first date. These subjects can ignite strong emotions and lead to heated debates, which may hinder the development of a positive connection.

It’s crucial to be mindful of body image and avoid making comments or asking questions about someone’s physical appearance or weight. Everyone has their own insecurities, and it’s important to create an environment where your date feels accepted and comfortable in their own skin.

Additionally, it’s essential to respect your date’s emotional boundaries by refraining from prying into deeply personal or traumatic experiences. While vulnerability is important in building trust, it’s crucial to allow your date to share such stories when they feel ready and willing.

Past Relationships

It’s natural to be curious about someone’s romantic history, but delving into their past relationships can be a sensitive topic. Opening up about past heartbreaks or discussing ex-partners can bring up negative emotions and create an uncomfortable atmosphere. Instead, focus on the present moment and the potential future you can build together.

Financial Status

Money matters are personal and can be seen as intrusive if brought up too early in a relationship. Asking about his income or financial situation may come across as materialistic or judgmental. It’s best to let financial discussions evolve naturally over time as trust and understanding deepen between you.

Deeply Personal Traumas

While empathy and understanding are important in any relationship, it’s crucial to respect boundaries when discussing deeply personal traumas. First dates should be light-hearted and enjoyable, so it’s best to avoid delving into sensitive topics that may trigger painful memories or emotions. Give the relationship time to develop before broaching such delicate subjects.

Religious or Political Beliefs

Religion and politics can be highly personal and deeply held beliefs. Discussing these topics too early on, especially without knowing your date’s stance, can lead to heated debates or misunderstandings. Unless you both feel comfortable discussing these matters, it’s best to keep the conversation focused on shared interests and experiences.

Health Issues or Medical History

Inquiring about someone’s health or medical history can be intrusive and may make your date feel uncomfortable. These are personal matters that should be shared at a more appropriate time when trust and a deeper connection have been established. Instead, focus on lighter topics that foster a positive and enjoyable atmosphere.

Marital Status or Future Commitment

It’s important to let the relationship unfold naturally without putting undue pressure on your date regarding future commitments. Asking about their intentions regarding marriage or long-term commitment too early can create unnecessary stress and expectations. Enjoy the present moment and focus on getting to know each other without rushing into the future.

Age or Weight

Questions about age or weight can be sensitive for many people. They may feel judged or self-conscious when asked about these topics. It’s important to create a safe and accepting environment where your date feels comfortable being themselves. Focus on appreciating their personality and character rather than making assumptions based on superficial aspects.

Controversial or Offensive TopicsFirst dates are about building a connection and getting to know each other on a deeper level. It’s best to steer clear of controversial or offensive topics that might offend your date’s beliefs, values, or cultural background. Keep the conversation light-hearted, inclusive, and focused on finding common ground.

Intimate Details

Intimate details about your date’s personal life should be shared when there is trust and a deeper connection. Respect their privacy and avoid prying into sensitive details about their past or personal experiences. Allow the relationship to develop organically and let them choose when and how much they want to share.

Future Plans

While it’s natural to be curious about your date’s future plans, asking questions that may put unnecessary pressure on them to reveal their long-term goals or aspirations can be overwhelming. Focus on enjoying the present moment and getting to know each other on a more personal level. As the relationship progresses, you’ll have ample opportunity to discuss future plans naturally and comfortably.

Family Issues

While family is an important aspect of one’s life, it’s best to avoid probing into sensitive family matters during the initial stages of getting to know someone. Family dynamics can be complex, and bringing up unresolved issues or sensitive topics can make your date feel uncomfortable or trigger negative emotions. Focus on getting to know their interests, hobbies, and aspirations instead.

Career Success or Failures

While discussing career aspirations and goals can be exciting, it’s important not to turn the conversation into a competition or to inquire about past failures. Your date’s professional journey is personal, and bringing up past disappointments or setbacks can dampen the mood and create an uncomfortable atmosphere. Instead, focus on their passions, interests, and how they find fulfillment in their work.

Personal Habits or Quirks

It’s important to give your date the space to reveal their personal habits or quirks at their own pace. Avoid asking direct questions about personal grooming, daily routines, or idiosyncrasies, as it may come across as invasive or judgmental. Let these aspects naturally unfold over time as you build trust and a deeper connection.

Legal Troubles or Criminal History

It’s best to avoid questions related to any legal troubles or criminal history your date may have had in the past. These are sensitive topics and may evoke uncomfortable or defensive reactions. Instead, focus on building a positive connection and discovering shared interests and values.

Excessive Personal Information

While it’s important to have open and honest communication, revealing excessive personal information on a first date can be overwhelming. It’s essential to maintain a level of mystery and allow the relationship to progress naturally. Avoid oversharing intimate details about your own life and respect your date’s privacy as well.

People say it is wrong to make assumptions, yet we do it all the time. What’s important is that the assumptions we make are calculated and for a good reason. Getting to know a guy these days is harder, and we often get attracted physically without first trying to make a more mental and emotional connection. These 13 questions are a good starting point to doing that. After all, that’s what conversations are made to do: for people to make connections.