Questions like, “What’s your favorite movie?” and “Where did you grow up?” may sound like great places to start an enlightening conversation, but in reality, they won’t get very far below the surface. If you want to get beyond the small talk to get to know a girl, here are the deepest questions you can ask her to find out what she’s really like.
- What’s been on your mind lately? As simple a question as this seems, it will tell you a lot more about a person’s mind than asking about their family or favorite tv shows. What a person thinks about reveals what they care about, what their values are, and where they are in their lives.
- When do you listen to music? While a certain breed of pretentious males think that a person’s music taste is the gold standard in compatibility testing, the music a person listens to is nowhere near as informative as when they listen. A person who listens to music when they’re sad will have a very different relationship with their feelings than a person who listens to music when they’re happy or pumped up at the gym.
- What is your biggest regret? This one is difficult for most people to answer, but if there’s a ready response, you’ll get a lot of important information. What people regret often indicates what their biggest weaknesses are–are they selfish? Do they care too much about what other people think? Do they take too long to make decisions? An answer to this question will tell you a lot.
- Have you ever stayed in a relationship for too long? Most people have struggled to let go of one relationship or another, but their reasons for doing so are often complex and unique. Hearing a potential partner reflect on an unhealthy relationship will give you a good idea of what their expectations and boundaries are.
- What makes you feel powerful? Every woman has something that makes them feel like the strongest, most beautiful version of themselves. Whether it’s a pair of killer heels, a mammoth workout at the gym, or standing in front of a boardroom full of people, the thing that makes a woman feel powerful will tell you a lot about who she is and give you even more reason to admire her.
- What person in your life do you turn to when you need advice? Mentors are some of the most important figures in a person’s life. Parents, teachers, and friends all play significant roles, but learning about the handful of people who a person trusts with their secrets and fears is one of the best ways to understand them.
- What do you love most about your job? A person’s profession takes up a significant proportion of their lives. Learning more about it is key to understanding the woman you’re getting to know. Instead of simply asking her what she does or where she hopes to be in five years, ask her what she loves about it. Hopefully, her eyes will light up and you’ll find out the real reason she chose her job.
- Do you have any secret talents? You never know what kind of strange tricks a person is hiding up their sleeve. You may think you’re going out with a straight-laced lawyer, only to discover that she competes in tango competitions or can hold her breath underwater for four minutes.
- If you had an infinite amount of free time, what skill would you like to work on? A lot of people have passions outside their work. Whether it’s piano or triathlons or learning a new language, everyone has something they’d like to improve. It may not be the first thing that they reveal about themselves to someone new, but it will tell you a lot about them.
- When did your last relationship end? You may think this is obvious and not worth mentioning, but it’s always a good question to ask so that you can understand where a person is coming from. For example, you may think that she’s cold and distant, only to find out that she got out of a serious relationship a few weeks ago and therefore needs to take things slowly at first.
- What’s the wildest thing you’ve ever done? Just because someone isn’t an adrenaline junky doesn’t mean they’ve never done anything exciting. In fact, people who are usually conservative adventurers are often shaped by experiences that happened when things didn’t go according to plan.
- What do you think respect looks like in a relationship? This is not a question that’s meant to make you look good. Sure, she may think more of you for having asked, but her answer is important if you hope to have a relationship with her. Every couple needs mutual respect, but this will not look the same for everyone. Establishing a common understanding of each other’s needs is crucial to having a successful partnership.
