13 nice questions to ask a guy on the first date

In a world where communication is so easily afforded by technology, it seems that we are communicating even lesser.

Messages are written across a screen often do not come about how we intend them to, so messages rarely get across. Perhaps we have lost a complete sense of conversation and just no longer know how to speak and the right way to ask.

This does not fare well in the land of men and women, where subtlety is not crucial and talking is a pastime long forgotten.

How does one compete with so many gadgets when there are just so many other things to do other than talk?

Fortunately, there are plenty of ways to get a guy engaged in conversation without making it seem so awkward and pushy.

The key here is to get the guy talking about himself by asking loads of open-ended questions.

Get him to think a little, and don’t allow him to either say “yes” or “no.”

Next thing you know, you’ll have conversation overload. Here are 13 creative questions you can ask a guy to get a good discussion going and the possible answers you might end up getting.

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.


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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.

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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.


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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.

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.