10 Casual Questions To Ask A Guy That Will Tell You Everything You Need To Know

Finding out important details about a guy you don't know well can be a delicate balancing act. To appear casual while still gathering the information you want, consider asking some of these questions.

1. "What's You Favorite Sports Team?"

Understanding if the person you are interested in dating has an addiction to Fantasy Football or a strong dislike for organized sports will give you insight into how they spend their leisure time and what they value. Are they someone who is excessively devoted to their team, or are they more balanced in their sports fandom? If you share the same interests, this question can also help determine your compatibility.

2. "Politics Are Crazy These Days, Huh?"

In today's world, most people try to avoid discussing politics, but if your potential partner's political views are a deal-breaker, it is essential to know where they stand. If you are fortunate, they may express frustration with the topic and suggest discussing something more productive. If so, you can move forward and suggest another conversation topic.

3. "Where Was Your Last Vacation?"

The destination one selects for a vacation can reveal a lot about compatibility. For example, if you are someone who thrives in a city atmosphere and discover that your date prefers a week-long trek into the Australian Outback or the Amazon rainforest, you may have clashing ideas of what constitutes happiness.

4. "Who's Your Favorite Actor?"

When you ask your date who their favorite celebrity is, their answer can provide valuable insight. If they respond with something like, "Scarlett Johansson because she's attractive," it may indicate that they are shallow and insensitive. On the other hand, if they mention an actor such as Mark Wahlberg and cite their admiration for the "Transformers" movie franchise, it could reveal their level of artistic sophistication, which could be a deal breaker or a selling point.

5. "What Was The Best Part Of Your Day?"

One straightforward inquiry can offer a glimpse into your date's values. For instance, a man once shared with me that the highlight of his day was giving a high-five to a child he encountered while cycling to work. I found this gesture adorable and endearing, and it was a deciding factor in our continued relationship.

6. "What Was High School Like For You?"

The more ambiguous the question, the more illuminating his answers will be. While high school is often a low point for people, his response to questions about this time can reveal a lot about his character. For instance, if he claims to have been the captain of the football team and dated all the cheerleaders, or if he admits to being a computer geek who spent his days playing video games alone, you'll gain a better understanding of the type of person you're dealing with.

7. "Have You Ever Spent Way Too Much Money On Something You Wish You Hadn't?"

In case he denies, it will be apparent that he is not telling the truth. However, if he answers truthfully, you will either find out that he is a decent guy who manages his finances prudently or someone who is inclined to make reckless decisions. It would be wise to respond to this question as well, providing him with something to work with.

8. "Do You Like Your Job?"

Does the man you're dating have lofty ambitions, or is he content with mediocrity? Is he diligent and hardworking, or does he prefer to be lazy? Does he value his work, or is he only interested in earning a paycheck so he can enjoy his free time? These are all essential questions that can be answered by simply asking whether he enjoys his job.

9. "What's The Worst Online Date You've Ever Been On?"

These days, almost everyone has had a brush with dating apps, which means that practically everyone has at least one dating app nightmare. Hearing about others' dating horror stories can be entertaining, but it can also reveal much about their judgment of people and the type of individuals they choose to go out with.

10. "So, How Do You Think This Date Is Going?"

While it may scare him to death, asking this question may also catch him off guard enough to elicit an honest response. On a first date, you have little to lose, and being candid with each other can transform the evening into a tremendous triumph (or allow for a quicker exit), rather than settling for another mundane, formulaic first date.