6 Deep Questions To Ask On A First Date If You & Your Date Are Feeling Comfortable

You've got a first date on the calendar — eeek! What will you wear? Will you be compatible? What will you talk about? Whether you were set up by mutual friends, found them on a dating app, or met while in the checkout line at Target, there's probably a lot you don't know about this person yet. Assuming things go well and the conversation is flowing, you might want to come prepared with some deep questions to ask on a first date.

First dates can be totally awkward, but sometimes, they can be surprisingly smooth and refreshing. If you and your date are vibing from the get go, you might consider taking the conversation to the next level. Some women may shy away from asking their dates more serious questions, but first dates are all about getting to know each other, right?

I mean, you made the time in your schedule, you threw on a killer outfit, and you made sure your makeup was on point. You might as well make the most of a first date and see how compatible the two of you really are. So, if you're pretty sure your date is feeling it, what are the best questions to ask beyond covering the basics about your jobs, school, hobbies, and living situations?

If you and your date are feeling comfortable on date one, consider asking these six deep questions.

Are you looking for something serious?
Stocksy / Guille Faingold

A lot of women avoid asking their date if they're looking for something serious right away which is totally understandable. This can be scary to ask, and you may worry about appearing intimidating by bringing it up. However, it's a completely fair question.

Learning what the other person is looking for when it comes to dating it's part of getting to know each other. If you're looking for different things, you might be relieved to figure it out on day one as opposed to two months from now. Of course, you might not be looking for something serious yourself, but either way, it's worth getting on the same page sooner rather than later.

Are you close with your family?
Stocksy / Lumina

If family is super important to you, you might want to consider asking your date how they feel about theirs. A person's relationship with their parents and siblings (or lack thereof) can sometimes reveal a lot about them.

In addition to learning about how they value family, asking this question might also give you a little insight into how they grew up, what traditions are important to them, and whether they have aspirations about starting their own family in the future.

Have you been on any bad dates lately?
Stocksy / Santi Nunez

You might think asking your date about their recent dating history is little forward. But if the vibe is right, go ahead and ask them if they've been on any bad dates lately.

Most likely, their answer will give you an idea about what they're not looking for, and maybe even open up the conversation for a good laugh. You also might learn how active their dating life is and whether or not they're seeing multiple people at once. If you've been on any recent less-than-satisfactory dates yourself, you can exchange horror stories.

Are you religious?
Stocksy / Lauren Naefe

Religion can be a personal, and sometimes sensitive, subject. However, if the conversation is carrying on naturally, you may want to ask your date about their beliefs, practices, and involvement with religion.

Whether you're religious or not, learning about your date's faith, spirituality, or indifference to religion could be a major indicator about how compatible the two of you are. If you follow different religions or one of you is more spiritual than the other, it doesn't automatically indicate that you're a bad match. It's all about getting to know someone and gaining insight about the important (or not important) things in their life.

How important is ________ to you?
Stocksy / Jennifer Brister

What are the most important things in your life and what are you day-to-day priorities? For you, it could be exercise, healthy eating, work, school, travel, voting, sleep, feminism — or any number of those things combined, you name it.

Think about what's most important to you, and fill in the blank with this question. It might help you get a clearer picture about whether or not your goals and priorities align.

When was your last serious relationship?
Stocksy / Boris Jovanovic

Finding out when someone's last serious relationship was might give you clues about what their commitment style is like. You might also find out if they've ever lived with a partner, why their last relationship didn't work out, if they are still hung up on an ex, and how ready they are for a new relationship. This question can also help you gain insight about any emotional trauma they may have experienced with an ex. It's also possible that they've never been in a serious relationship. If your date doesn't offer this information to you, you won't know unless you ask. Just keep in mind that a person's relationship history will not necessarily play a part in their future relationships, so don't be too quick to pass judgment.

When you're on date one, and the initial small talk is going a little better than you expected, it could be worth asking some deeper questions. Plus, if you're on the shyer side, having some questions ready to go in your back pocket will help you break the ice during the date. I'm not saying you should literally pull out a piece of paper and start rattling off a list of personal inquiries, but being prepared never hurts. A lot of people get nervous on first dates, and this could have an impact on their responses to your questions, so try to not take everything they say too seriously. Also, if the conversation isn't flowing, it doesn't always mean a second date is off the table. Plenty of bad first dates turn in to incredible long-term relationships.

Although scrolling through the last four years of a person's Instagram can show you what their highlight reel looks like, you can only find out so much by cyber-creeping on someone. First dates are all about assessing one another and figuring out if you could be an IRL match, but don't forget to have some fun too. Be yourself, keep an open mind, and see where the date takes you.