5 Questions To Ask The Person You're Dating If You Want To Build A Genuine Connection

by Anjali Sareen Nowakowski

Having a crush is really exciting. (Although, it might not seem like it sometimes.) You're caught up in lots of pleasant feels, daydreams, and getting to know someone better. Did you know there are certain deep questions to ask your crush that will help you strengthen your connection and help you figure each other out? There are!

What's even better is you can use these questions to start conversations with your significant other, too. They aren't just reserved for crushes. These five questions are designed to give you significant insight into another person because they ask about what makes them them, rather than more superficial questions, like their favorite color or sport.

These questions will also help spark a conversation between you and your crush, so it will be more like a deep, getting-to-know-each-other discussion, rather than just a question and answer session. In fact, these five questions were the same ones I asked my husband within our first few weeks of dating. They helped me get to know his background and personality. And similarly, he got to know mine.

So, when you get the chance, here are five deep questions to ask your crush to get to know them better.

1. "What Was Your Childhood Like?"

Asking someone about their childhood may not be a great conversation opener, but it is a great way to get to know them.

Instead of asking a specific question about their childhood, like if they played sports or how good they were in school, asking someone about their childhood generally will give you a big picture of what they consider important and what things stick out to them about their childhood. They may end up telling you about their parents, their favorite subject, or even a childhood best friend.

No matter what they decide to open up about, you'll get a greater insight into their personality. And it's likely that they'll turn around and ask you about your childhood, too, which will spark a really interesting discussion.

2. "What Are Your Personal Dreams And Goals?"

Asking someone about their work goals is generally pretty accepted discourse. After all, one of the most basic questions we ask other people when we meet them for the first time is "What do you do?"

Accepted or otherwise, asking someone about their work won't really give you great insight into them as a person. Often, we work because we have to, and even if we are some of the lucky few who truly love our work, it isn't what drives us as people.

Instead, ask your crush what their personal goals and dreams are. You'll probably find out some things that surprised you. For example, they might tell you they have a dream of moving to a foreign country or of being a surf instructor or something else you could never have expected. This question will truly tell you what they are striving for, and because of that, you'll get to know more about them as a person.

3. "What Do You Consider The Hardest Experience Of Your Life?"

This may be a difficult question to ask, but it's often a great one to give you insight into someone's personality. Asking someone about the hardest experience they have ever faced will let you know how they feel about adversity, as well as how they overcame that adversity. It'll also tell you what they consider difficult, on an interpersonal level.

Not only that, but our most difficult experiences in life are not often things we get asked about or things we discuss. Because of this, asking your crush about it will open them up to a new experience of talking about it. They'll likely be surprised you asked, and they may be a little hesitant to discuss it. But if you get through, and they open up, it'll be a great bonding experience.

Be aware that they may also ask you this question about yourself, so you should be ready to open up and answer it, too.

4. "What Is The Most Valuable Thing You've Learned To Date?"

This is both a hard question and a fun one. It can be difficult to think about the most valuable thing we have learned as humans, but it's also something that makes us delve deep into our own personalities. It makes us think about what we value and why we think something is valuable.

For me, the answer to this question is "to always be kind to people," but I didn't realize that until I was asked this question, and I had to sit there and think about what I truly valued. If you had asked me a few years ago, I might have said something about being a lawyer or getting through school, but now, my answer to this question tells you a lot more about me as a person.

Similarly, asking your crush this will help the two of you connect because you'll be revealing a lot about yourselves (assuming your crush asks you back, of course).

And it's a great conversation starter about other things you've learned.

5. "What Would You Do If Someone Gave You $1 Billion?"

Of course, even if some of us like to work, we probably wouldn't if we didn't have to. But what would we do instead? Well, the best way to find that out about your crush is to ask.

What they would do if they got a billion dollars will tell you a lot about their personality. Would they move somewhere? Would they travel full-time? Would they open a rescue? Would they donate it at all? Would they build a giant house?

It's not only a good question to help you get to know your crush, it's also a great one for them to think about, because it's fun! It'll put them in the mindset of having that much money to spend however they want. And of course, if they ask you, too, the two of you can have a great time going back and forth about what you'd do with the rest of your lives.

Having a crush is fun, but getting to know your crush is even better. Asking these five questions will help the two of you form a stronger bond, and at the end of it, you may find out some things about your crush that you never knew.

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