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Top 30 Questions to Ask a Girl You Like

By Emyli LovzDecember 13, 2018Conversation
Questions to Ask a Girl You Like

What are the top questions to ask a girl you like? When it comes to building a romantic connection with someone, the conversation is key. Moreover, you need to ask the right type of questions to win her over. When you ask the right questions before asking a woman out and during your dates, it’s easier to escalate sexual tension and discern whether or not this is the right person for you.

But coming up with questions to ask a girl you like can be easier said than done. That’s why I’m taking out the guesswork for you. Below, check out the top 30 questions to ask a girl you like. More specificially, we’re going to be breaking these questions up into the following five categories:

  • Before she knows you want to date her
  • Questions to get her on the first date
  • Questions to ask a girl during a first date
  • Questions to ask a girl during a second date
  • Questions to ask a girl during a third date

Questions to Ask a Girl Before She Knows You Want to Date Her

It all starts with actually getting her to agree to go on a date with you. And you need to play your cards right here. You don’t want to come off as overly aggressive but you also don’t want to fall into the trap of being too much of a shy guy or a nice guy. The following are some strategic questions to ask a girl you like before she knows you want to date her.


Question #1: What is Your Name?

This is most definitely the first step when it comes to questions to ask a girl you like.

In case you literally just met her, you want to find out her name first and foremost. And when you ask her name, make sure that you’re using great eye contact and smiling. This will put her at ease and show her you might be interested in her.

Question #2: Are You Here with Your Boyfriend?

You can ask her this or “Do you have a boyfriend?” if you’re chatting with a woman you just met in real life. If you met her on a dating site or app, you can assume that she’s single. But you want to make sure she’s unattached as quickly as possible before asking a girl out.

Question #3: How Would You Describe Your Perfect Saturday?

You want to ask this question (or some version of this question) to learn more about a woman’s interests. The first step in building a connection with someone is building trust and rapport through shared interests. For that reason, it’s really important that you figure out what you have in common so that you can craft a compelling date around that interest.

Once you’ve had some banter with a woman and established a flirtatious vibe, it’s time to ask her out on an actual date.

Questions to Ask a Girl to Get Her on the First Date

Once you understand her interests, it’s time to get her to commit to a first date with you. You can do this by asking the following.

Question #4: When Are You Free This Week or Weekend?

You want to be able to hone in on a time she’s available so that you don’t end up going back and forth about scheduling a date.

Question #5: Ask Her Out Using a TDL

The specifics of this will vary depending on her interests. But whatever you come up with date-wise, you want to make sure that you ask the girl out with a TDL.

What is a TDL?

A TDL is an acronym that stands for time, date and location. It’s what we here at EmLovz use to refer to a date’s call-to-action.

Every male client I’ve worked with has experienced more success and less rejection when asking out women using a TDL.


Whether it’s when meeting guys online or out and about, women encounter men who ask them out with a simple, “Do you want to go on a date with me?” and no real plan to back up the question — they simply want a “yes” or “no” answer to the question. When you don’t use a TDL, you and the woman are often stuck in a back-and-forth conversation, trying to figure out the best place to go and a time to meet.

When you use a TDL, you stand out from other guys by showing that you know how to take initiative and are also showing chivalry by being considerate of her time. She doesn’t have to worry about coming up with any plans or engaging in a frustrating back-and-forth with you on what time and place works for the both of you when it comes to the first date.

Make the Date Compelling

Compelling dates are ones that speak to the woman’s interests and also offer her a brand new experience. I will get a little bit more into what makes a date compelling later in this article.

For example, let’s say the girl you want to ask out is a big yogi. You could look up a fun yoga event or unique class (like karaoke yoga or cat yoga) and ask her if she wants to go with you date-style.

Questions to Ask a Girl During a First Date

You got her to agree to go on a date with you. Congrats! Now it’s time to make a great impression. The purpose of the first date is to establish trust and rapport through shared interests. You’ve already set up a compelling date with a TDL, so the environment should help to stimulate conversation and set a comfortable mood.

But you’re still at risk of awkward moments and lulls in conversation wide enough for tumbleweeds to roll through. Combat this by asking her the following questions on a first date.

Question #6: What is Your Best Childhood Memory?

Enjoy exchanging reveries and take note of the memories that she describes as most special to her. Like other things on this list, her nostalgia could provide a roadmap for a future date.

For example, did she used to love riding the Ferris wheel each year during an annual fair that took place every summer in her hometown? Recreate that memory by taking her to a fair or carnival in the future.

Question #7: What Hobby Would You Like to Get Into if You Had Unlimited Time and Money?

We all have things that we’d like to get into but, due to work and other obligations, we don’t have room for it in our schedule. Find out something that she’d like to get into but hasn’t yet. You can possibly even use this information to come up with great future date ideas with her!

Question #8: What’s the Most Recent TV Series You Binged or Rewatched?

This is a great way to bond and even laugh over some quotable moments.


Question #9: What’s Your Philosophy on Tipping?

Fact: If you are a terrible tipper, you might also be a terrible person. This isn’t always the case except for when it is, which is often.

It’s good to find out early if your date is a terrible tipper. And you can also impress her by letting her know you tip at least 20%, even if the waiter is subpar. Women like men who are good tippers, FYI.

Question #10: What’s Your Biggest Pet Peeve?

It’s good to learn this early on so you have one way to avoid unintentionally irking her.

Question #11: What Do You Do Professionally?

Assuming the person you’re on a date with works, ask more about their job and show interest by asking the following questions:

  • What made you get into that line of work?
  • What do you like about it?
  • What do you not like about it?
  • What is your dream job?
  • If she’s an entrepreneur, ask her what type of business she’d create if she had unlimited resources.

Question #12: How Would Your Friends Describe You?

This is a great way to learn more about her personality and also delve into the type of company she keeps.

Question #13: Are You More of an Indoors or Outdoors Person?

Although I consider things like hiking and picnics a great second date idea, if she HATES the outdoors, you want to steer clear of any date that doesn’t involve four walls and air conditioning.

But with that said, if you LOVE the outdoors, don’t pretend to also HATE the outdoors just because she does. Being an agreeable man will get you nowhere with women.

Question #14: How Would You Like to Go [Insert Awesome Second Date Idea Here] With Me This Saturday?

Obviously, if the first date is going well, you want to set up a second date. IMPORTANT: Don’t wait until the next day or a few days after a first date to ask her out. Get it set up by the end of the first date to ensure success. If you’re interested in learning more about how to structure a successful first date, check out my article on First Date Tips for Men for deeper strategies.

Keep in mind, the second date should be something active and free.

Questions to Ask a Girl During a Second Date

The purpose of the second date is to escalate sexual tension. That’s part of the reason I advise my clients to choose something active, like hiking, cycling, visiting a museum or exploring a new neighborhood. This gives you opportunities to break the touch barrier without coming off as creepy.


You’ll be helping a girl with equipment, climbing up a steep hill or preventing her from falling during something like a roller skating date, which allows touch to occur organically.

Because you’ve already gotten through the first date, the second date also offers opportunities to go a little deeper when it comes to conversation.

Question #15: What Was the Most Recent Relationship You Were In?

Obviously, you want to pose this question in a non-threatening sort of way. But this can also be a great way to take inventory of any potential red flags.

If the girl you’re on a second date with JUST got out of a relationship, there’s a chance she hasn’t had proper time to heal from the heartbreak and could be emotionally unavailable.

Question #16: What Made You Decide to Go On a Second Date with Me? 🙂

Make sure you pose this question in a fun, casual and flirty way. Obviously, there are things about you that this lady enjoyed on the first date — so much so that she agreed to a second date — so why not hear about all the awesome things about yourself?

And in return, make sure you let her know what was captivating about her, that it made you want to spend more time with her.

Question #17: What’s One Thing You Enjoy Doing That Can Make You Completely Lose Track of Time?

This allows you to learn more about her passions, bond over shared interests and think about potential future dates.

Question #18: If You Could Change Anything About Yourself, What Would it Be?

This allows you to learn a bit more about her and you can offer something that you’d like to change about yourself as well. Even the most confident people have things they’d like to improve, and if you can talk about things you’d like to work on with humility and confidence, it’s very attractive. Being vulnerable with your dates is super important and a great way to speed your overall connection.

Question #19: Two Truths and a Lie

Ask her to give you two truths and a lie, and try to guess the lie. Then do the same and have her guess. This is a really fun way to keep the conversation going on the date and learn some fun facts about one another.

Question #20: In Your Opinion, What About a Guy Turns You On?

This is a great way to escalate sexual tension and build chemistry without being overly aggressive.

Question #21: If You Had a Crystal Ball, What Would You Want to Know?

This is another way to get to deepen your knowledge of someone — and possibly even find out something unexpected — without posing a question that seems threatening or too personal for a second date.


Question #22: Would You Like to Go [Insert Awesome Third Date Idea Here] with Me on Saturday Night?

Just like the first date, you shouldn’t wait until a day or a few days later to set up a third date with a woman. If you like her and things are going well, set the date up then and there.

The third date is one where you can go all out with a romantic dinner with the goal of firming up your bond with her. But be true to yourself – make sure you see a potential future with this woman before committing further time, energy, and finances on her.

Personal Questions to Ask a Girl During a Third Date

Once you get to a third date, it’s time to figure out whether the two of you are a good fit as far as morals and values go. During this date, you can dive deeper and allow yourself to become more vulnerable. The third date is especially important because it can really show you whether or not the two of you have long-term potential. Moreover, the third date is often when physical intimacy occurs.

Question #22: What Are Your Spiritual Beliefs?

At this point, you’ve likely built a strong enough connection that you can enter the spiritual, religious and political territory. The most important thing to remember in these circumstances is to respond without judgment and to keep an open mind.

Question #23: How Do You Lean Politically?

Politics can be extremely polarizing, which is why I don’t recommend treading into political territory very much until the third date. As with spiritual beliefs, be sure to respond without judgment and an open mind.

Question #24: What Are Your Views on Gender Roles?

It’s important that her beliefs align with yours if you want to have a relationship without a ton of contention.

Question #25: If You Had to Pick Three Top Values, What Would They Be?

As I mentioned, the third date is often the make or break one — you could realize you don’t want to continue on to a relationship, or this could seal the deal for both of you.

Learning about what she values — and vice versa — is important, because having similar values is part of what makes for a healthy and successful relationship.

Question #26: What’s Your Guiltiest Pleasure?

This is a fun and flirty type of question where you can exchange stories and can potentially even start to get her in the mood.

It’s important for me to note at this point that you should definitely be stoking the sexual spark between the two of you by touching her. During moments of laughter when you ask these sorts of questions, be sure to practice some touching on her knee, shoulder, elbow and other non-threatening areas. At this point in your dating stage, you’ve likely become close enough as well that you can clasp her hand across or under the table.

Question #27: What Are You Most Grateful for Right Now, At This Very Moment?

Make sure to ask follow-up questions (“why?” “has that been a goal for you for a long time?”) to keep diving deeper. And make sure to share what you’re grateful for as well.


Pro tip: Add some extra flirtation by following up with something like, “Well, I’m definitely grateful that you agreed to go on a third date with me.” This is practically guaranteed to make her swoon.

Question #28: What, If Anything, Is Too Serious to Be Joked About?

You’ve been tackling some sensitive topics during this date. For that reason, it’s also important to find out what could be too sensitive of a topic for her so you can avoid an unintentional offense.

Question #29: Which Celebrity Is Number One On Your “Freebies List”?

Let’s lighten the mood.

Many couples have a “freebie list” that consists of five (or more if you feel like being GREEDY) celebrities that they would be allowed to hook up with if the opportunity presented itself, and said hookup wouldn’t be considered cheating.

I like this question just because it’s fun and silly, and it shows you’re secure with yourself, i.e., you’re not the type of guy to puff his chest out and see red when your girl swoons over a Ryan Gosling poster.

Question #30: Have You Tried This Rare Drink?

This final question can be weaved into your third date bounce back (as in, bounce back to your place) plan. Knowing how to make a tasty, little-known drink can be one of a few compelling reasons for a woman to come back to your place and potentially seal the deal.

There are several easy drink recipes out there, some that use as few as three ingredients.

Questions to Ask a Girl When it Comes to Consent

One thing that is extremely important to keep in mind when you’ve gotten to a third date with a girl is consent. Because this date often leads to physical intimacy, you need to be sure that the woman’s comfort level is a priority.

As things heat up, check in with her to make sure she’s comfortable with what’s happening and also enjoying it. If a woman freezes up or becomes unresponsive, stop and check in to make sure she’s ok. Some guys worry that asking too many questions will kill the mood. But honestly, a woman is going to appreciate your attentiveness and the fact that you’re putting her security and comfort first.

Any Questions? Contact Me Today!

Want to learn more about questions to ask a girl you like. How about literally any dating topic under the sun?

I’ve worked as a dating coach for years since completing my viral 100-date experiment. Since then, I’ve been helping men across the world find lasting love. I’d like to do the same for you.

Whether you’re trying to optimize your success in the dating world, need help navigating through issues in your current relationship, or need help moving forward from a breakup, I’m here to help.


Head over to my calendar and book a 1-on-1 Skype session today. During our session, we will create a comprehensive, individualized action plan designed to help you overcome your roadblocks and crush your goals.

I look forward to connecting with you.