When you're getting to know a guy, you need to seem super casual, but still be able to get your answers. You do not want to be too abrasive and scare the guy away, but neither do you want to be misinformed. Balancing between being tender and cautious and feeding your curiosity can be a tough act. To ease the burden for you, we have compiled a list of super chill questions that will let you into the deeper life of any guy you're interested in.

Ask him about his worst online dating experience

Almost everyone has tried out a dating app. When you ask him about his worst dating experience, it'll give you something to laugh and bond over. Furthermore, you'll get to see the kind of judgment he exercises, and how rational he is.

Ask about his favorite sports team

Most guys are sports enthusiasts. When you ask this question, you will get a rough idea of how the guy spends his free time. You will also see if your sports interests match with that of his, or if any of you could adjust or tolerate each other. Finally, from the way he will talk about his team, you'll know if he's so obsessed that he'll neglect date nights.

Ask him about his last vacation

Where a person chooses to spend their free time says a lot about them. There's an art to choosing a place to vacation. When he tells you where he vacationed, see if it would be on a list of your top vacation spots. Again, this is one of those things that are light towards the beginning of a relationship but tend to pick up weight as the relationship intensifies.

Ask him about his political views

Politics are a tricky subject to navigate. It takes courage, the correct wording, and perfect timing to pull it off correctly. It may not matter at the moment, but when you do get into a serious relationship, political views will play a pivotal role. However, don't play too much into politics; there are dozens of other interesting subjects to talk about.

Ask him about his favorite actor

If the relationship takes root, one of the things you might find yourself doing is going to the movies. When you ask him about his favorite actor, he is likely to follow it up with a reason as to why. When you know what sort of movies he's into, you can compare if it's compatible with your list.

Ask him about the best part of his day

Different people give priorities to different things. Consequently, they have times of the day they feel make them happy. When you're beginning to know a person, knowing what a person looks forward to each day will give you a sense of their values.

Ask him if he's ever spent a lot of money on something, then later regretted it

Every now and then, we make hefty purchases on things we think we want, only to later regret the action. The trick here is to see how responsible he is with his finances. You're also trying to see if he learned from his mistakes.

Ask him about his high school experience

High school years are a formative period for most people. It is at this time that beliefs and ethics are formed. For example, if he tells you he was the captain of the football team and dated all cheerleaders, it'll give you an example of the kind of person he is. That would be very different from if he was a geek who spent all his time around a computer.

Ask him if he likes his job

His job will give you a sense of his ambitions. It doesn't have to be a high-paying job, but the way he talks about it will tell you if he has the drive to move forward. An ambitious person will have a plan on how to get to the next step. A person with no ambition, on the other hand, will wing it from one day to the next.

Ask him how he thinks the date is going

Most likely, this is going to catch him off guard – which is a good thing. The randomness of this question will most likely elicit an honest answer. This will then give you perspective on what he thinks of you and the time you've spent.