Good, Deep & Interesting Questions To Ask A Girl You Like

Written by on August 1, 2016

Published in Dating, Females

Alright bitches. Knowing how to talk to a girl you like without spewing babble in a varied array of situations is essential to being an Untroubled & Strong man. Not to mention crucial in the quest for entering the joyful warmth of a women’s loins. In this post I will drop some knowledge bombs around the most common situations a modern man may find himself in and good questions to ask a girl in these situations.

In fact you may be wondering, “What are the best questions to ask a girl?” or, “What are questions to ask a girl you just met?”

Well, we will get into that but instead of asking what questions to ask, start thinking about what makes a good question? Specifically for dating.

Specifically I will cover texting, first dates, and flirting. All questions in these 3 areas are designed to maximize her attention & keep her engaged. Which is what you need to accomplish should you so desire to capture your elusive prey. I wanted to have 20 questions to ask a girl but I think I ended up with a bit less.

Forgive me.

20 questions to ask a girl

Questions To Ask To Get To Know A Girl Over Text


How to start a text conversation with a girl? Isn’t that the age old question of the 21st century? Whether you are trying to start a conversation, ask a girl out, or get a girl re-engaged in conversation– the right question makes all the difference. Especially if your looking for questions to ask a girl you like. I would assume you like the girl if your searching for advice on asking her questions, I highly doubt you would be spending valuable time practicing game for a girl you weren’t into.

Anyway, I digress, as a general rule of thumb never simply text anything along the lines of, “Hey, what’s up?”. It’s boring. It makes you look no different than every other guy out there.  You wanting to be thinking of, “What are interesting questions to ask a girl?” If  you don’t think it’s interesting, she probably wont too. Throw some humor in the mix, let a bit of your personality come out! If she isn’t feeling it, she’s probably not a good fit anyway. By taking risks with humor out of the gate, you weed out a bunch of women that would be bad fits for you anyway.

Some lines to replace the usual “What’s up”

  • “So what kind of trouble are you getting into today?”
  • “ Living the dream today?”
  • “ How is adult-ing going today?”
  • “Are you making good choices today?”
  • “ How goes the insanity of life?”
  • “Requesting status update”

Some of you are probably thinking “Those are fucking lame.” And they are, but each one of those I have successfully used on a girl I thought I had no business chasing. Even if they are lame, the fact that you’re confident enough to swing and miss women find attractive. Some even find it more attractive than a swing and a hit. The untroubled man isn’t afraid to be himself. Women can sniff out fakeness like a basset hound. Worry less about the line and more about if the humor is sincere. Furthermore remember some of these for the purpose of having questions to keep a text conversation going as sometimes you may have to prime the pump a few times before the convo really takes off.

I can’t really give you a straight list of funny questions to ask a girl because “funny” is situational and I am no comedian. But again, don’t be afraid to have a joke fall flat. The more you practice the better you will get. So here we go with some savvy questions to ask a girl to get to know her.

interesting questions to ask a girl

Asking Girls Out Via Text


The prelim question

A tactic I have used often is to prime the pump to the actual asking her out is ask question probing her availability, and answer for her in the same text with something outrageous. When you ask a girl what she is doing at a certain time, she knows that you’re looking to hang. She also knows if your looking to hang it’s because you’re really looking to bang.

But you can’t be that blunt. Women like you to hide the truth in clever games and humor.

So take a normal question like, “What are you up to this weekend?” try sending something along the lines of, “What are you up to this weekend? Blowin’ dudes behind the dumpster for change? I knew it….”

Or something less crass depending on the girl. You get the idea.

Don’t ask, entice

When actually asking a girl out over text, you want to make the date as enticing as possible. Don’t just ask, “Wanna snag some drinks friday?” That sounds pretty standard. Instead ask something like “What are your thoughts on delicious street tacos, tasty beverages and live music?”

Get her to imagine all the great benefits that come with going on a date with the man bag of testosterone you are. The more excited she feels the better chances you have.

How to ask a girl out over text (without actually asking her out)

Send an open invitation to join you in something you’re already doing anyway. Or at least make it seem like it would be something you’re doing anyway. This eliminates the tension that comes along with asking her on a formal date. This is a gamble though, often asking for an official date has more tension, but women are attracted to the confidence. I use this tactic usually after a first date where I have already made it clear with confidence I am interested. Possibly if I haven’t talked to her for a few weeks, I will invite her to an activity I am “already” doing. You can do this with group activities or something like running errands.

Example : “I need some new clothes and could use a girl’s eye to help me find pants that bring out the lusciousness of my buttocks.”

Like before, humor is your friend. Playful is your friend. Women feel what you feel and if you’re feeling fun, they feel fun and associate you with that feeling. If you don’t think you can pull off the humor then fall back on being confident and clear.

Re-engaging a girl via text

Same principle applies here, use playful banter. You know and she knows that communication has been fizzling. No need to draw attention to that, rather come out of nowhere with something funny and outrageous. Remind her of why she was interested in you before. Ideally combine this with the above advice inviting her to an activity that is enticing. Don’t just attempt to re-establishing contact, but go for the home run.

Funny, enticing & confident. Hit her with dat’ triple threat baybee.

Example: “Enjoying some sun and barbeque at the pool. I am in desperate need of somebody to feed me grapes while my impeccable bronzing body is sitting on this beach chair like it’s the Iron Throne.”

Last resort message

If re-engaging plans have fallen flat multiple times and your pretty positive she’s escaped your hunt don’t hesitate to just say “fuck it” and go for the hail mary. She’s probably escaped your wrath anyway.

Hit her up with something that basically implies if she doesn’t respond you are moving on. 8/10 times she won’t, but the other 2 times she will. That’s 2 more chances you wouldn’t have had.

Example: “ Due to my ever increasing popularity and societies outrageous demand for my company, I need to clear up space in my phone for more contacts. Am I deleting your number or not?”

Define Your Standards

In order to ask good questions if you manage to schedule a first date, you must first know yourself. If you don’t have an idea of what you want in a partner, then any date has a higher probability of being a waste of time and money. You won’t know what to ask or what to look for. Besides generating interest in you for her, questions also serve the purpose to help you quickly decide if you have interest in her.

Ask yourself things like:


  • What are 3 things you really want in a partner?
  • What are your life goals?
  • How do you want to feel around them?
  • What are 3 things that are deal-breakers?
  • How do you NOT want to feel around them?
  • What are things you can tolerate, but would rather not deal with?

Your rules will change over time. They should change. That’s a healthy sign. But you gotta start somewhere. If you are not sure, just write down what comes to your mind. You can rewrite it later. 

A women is attracted to a man that knows what he wants. They can sense it. For your sake personally and to up your game you gotta nail down a starting point on what you want not just in a partner but in life as well.

Plus women can tell if you have developed a strong sense of self or not. It is in their DNA to be attracted to authenticity and stability. If your sense of self is not solidified, then no matter what pick up skills you think you have, it is going to be an uphill battle. The mark will get away.


funny questions to ask a girl

Asking Questions on Dates

I get it — it can be really difficult to know how to break the ice and start a conversation. Once you do get a conversation flowing, it can be difficult to keep the momentum moving forward. Which is why preparing a solid game-plan with standard questions you can basically use on anyone is beneficial.

But having prepared questions can have a drawback. If your prepared questions suck or come across….well prepared, then your screwed. That is why you want to focus on having open ended questions for dating purposes.

However, even better you need to know what makes a good question so you can come up with your own questions on the fly, in the moment. Good questions give you useful information, show sincere interest, and allow you to be authentic, confident & open. Questions that will spark her interest, while simultaneously help you decide if you’re even interested in her. Questions that avoid the conversational scripts we’ve all learned & that turn a dull, rote exchange into something fun and exciting.

What makes a question good?

Good questions have some basic characteristics.

  • Good questions derive from genuine interest. Don’t ask if you don’t care.
  • Good questions are open-ended. No Yes or No answers
  • They allow for some back and forth.
    • Ideally, a question should lead to more questions and promote going off on tangents. Tangents are good, it means she’s comfortable!
  • Good questions get people talking about subjects they’re interested in.
  • Good questions target getting to know her

Once, you have had some practice and you understand what makes a good question, it’s really not that hard to “wing” it and fire them off on the fly. You just need to ask a few questions to get the ball rolling and her answers will lead you the rest of the way. Also Some of you may have been looking for, “deep questions to ask a girl” and that is a good mindset in learning how to ask good questions. Shooting for “deep” questions is good, but you must ease into the depths of genuineness slowly. You cant come racing out of the gate asking about how she handles the deep seated fear all humans have which is awareness nobody really knows what the fuck is going on this pebble hurtling through infinity with texting apes sending dick pics on it.

She’ll probably think your a bit too intense if you open with something like that.

Dont just think, “What are deep questions to ask a girl?” but also combine that with, “What are interesting yet personal questions to ask a girl?” Keep her interested, keep her laughing all the while learning more about her for you. So you can decide if this walking bag of estrogen is even worthy of you!

This advice also works into dating if you are looking for personal questions to ask your girlfriend. Understanding good questions also continues to provide value into marriage should you ever decide to go that route.

Hell lets be real, good questions help with everything.

Anyway, it’s not a bad idea to have a some solid pre-meditated questions ready in case you hit a SNAFU or her immaculate beauty tingles your tip so hard you can’t think straight and go into dumb dumb mode.

Some of my fall back questions I have used are:

What was your favorite part of your week?”

Use this in place of the standard, “So what do you do for a living?” Chances are, you are legitimately interested in her vocation, but that question has some issues. First, it’s boring — she’s been asked that God knows how many times. Which in turn means she has answered that question a lot. Plus it’s not open ended as well as she probably doesn’t want to talk about work.

In contrast, “What was the best part of your week?” This forces her to talk about something she likes, which may be work but could also be yoga, binge watching Buffy the vampire slayer or whatever celebrity she’s been drooling over lately. Whatever she decides to respond with, she choses, feels empowered, feels desired and gets to talk about herself in the context she wants — and you get to listen. Now you’re focused on her fun, positive experiences, and the conversation will most likely start perpetuating itself. In turn she will associate the good vibes she experiences with talking to you. And thus your prey steps one inch closer to your trap.

Jokes aside, the question creates a  small window into her life . You can deduce quite a bit from what she chooses to tell you. She’s not going to give you a chronological breakdown of her week, but rather what she is most stoked on. This helps you decide if your into her as well.

“What’s the most frustrating aspect of dating?”

Technically this isn’t a positive question, but that’s ok. The purpose isn’t to get her to rant about dating or even get clues on what you shouldn’t do (although you will get hints!), but rather to be transparent about the fact dating is awkward, stressful and frustrating. This is a common ground you can find with any girl because it’s true for everyone. When you fire off this question make sure to smile big and maintain a lighthearted tone. If she’s into it, this can be a great springboard into swapping dating stories which is fun and also diffuses the tension.

This also has a benefit of opening up honesty and vulnerability on both sides. Something that is very important to women. She will recognize you have the confidence to be vulnerable and will in turn make her feel confident. She will associate this confidence with spending time with you.

Just inching toward that trap nestled in the brush ever so delicately.

“Who are you closest to in your family?”

Because this question is closed make sure to follow up with something like “How did you two become so close?” This forces her to talk about her family (usually a positive vibe) and opens the door for follow up questions.

When shooting off the follow up questions, use the tactic of recapping what she said (“Sounds like you spent a lot of time with your dad”) this shows you are listening and then ask a relevant question to pivot (“What about your mom? You have any traditions with her?”) This tactic of recapping and pivoting works not just for this question but any question and is a good habit to use in conversation with anyone, not just women.

“What’s your main goal in life?”

This may seem rote, but deliver it in a way that she knows you mean it for real. This gives her a chance to express what she really wants, what direction she is heading allowing you to decide if her goals have compatible overlap with your own.

“What do you like about your job?”

If you are going to ask about her work, do it in this way. You will find out where she works and if she even likes it. Does she want to switch jobs or careers? If so, why? If she likes her job you will find out why she likes it giving you more insight into determining her compatibility with you.

“What your favorite thing about your hometown?”

Very few people ask this question, this one will get her to think and drum up positive nostalgia emotions. Nostalgia is one of the most potent emotions and if you get here to associate that feeling with you, case closed.

If she hates her hometown, then pivot to have her tell you why she moved where she is now. Both possibilities again give you more insight to her compatibility.

“How did you two become friends?”

If you met her through some mutual friends, then unpacking how she knows who you know leads to organic conversation about your common ground. Your peers. If you met her through a friend, you can talk about that friend. Keep it positive always, bring out the funny stories. This will usually lead to story swapping about friends, roommates, road-trips, concerts etc. Again your drumming up positive emotions, attaching you to those emotions and getting to know her better all at once.

“What’s the best part of this city nobody knows about?”

You are letting her flex her expertise and feel special. You’re also letting her do the work in terms of coming up with date ideas.

Thats efficiency baby.

If she divulges to you some serious “secret” spots or gems and then invites you to go there with her. You then know she is feeling it. She wouldn’t invite you or bring up the notion of going there together if she wasn’t interested.

“What your favorite travel destination?”

Either she will tell you about her favorite place she has been, or what place she really wants to go. Both will create positive emotions, give you insight and angle you for easy follow up questions.


things to ask a girl

How To Tell If A Girl Likes You – Post Date Games

After the first date, or any dates for that matter there is always the issue of deciphering if she was and still is interested as well as cultivating and maintaining any interest you built up on the date. Some signs you can look out for to tell if she is into it or not. Maybe you want to be direct and are wondering how to ask a girl if she likes you straight up?

That’s not a bad move as no matter the situation its a confident play as well as being time efficient which is my favorite. But if your not into that here are some other ways to decipher her interest level.

Did she maintain distance?

Recalling the date if there was no opportunity to get closer to her because she was practically sitting at the next table, then she isn’t into it. Any female who isn’t interested will refuse to loosen her boundaries.  Conversely, if she ever went out of her way to touch you in any way shape or form., she’s into it. A brush on the shoulder, touching your hand, bumping into you playfully etc. This is a good sign. If she is maintaining distance like your the black plague she will want to pay for her share  of the meal to erase any guilt of rejection.

Let her drop them dolla’ bills. Use your saved cash on another mark.

At the end of the date, did she do any lingering? Or did she quickly go for the hug (or even worse the handshake) and bolt to the door like a gazelle running from a panther? If she lingered, you’re in. If she bolted, start looking for another girl and don’t bother hitting her up again.

How long was the date, how many drinks did she have?

The number of drinks ordered is a 100% accurate method for telling how long someone wants to stay during a date. If she’s done after the first drink? She wants to leave. Don’t fall for excuses, end the date as quickly (and casually) as you can. She is going to say things like, “ I need to drive.” or, “ I have work in the morning.” or whatever other bullshit women make up because they feel it’s impolite to tell you off bluntly.

If I am wrong and her reasons are legit, then she’s for sure going to want to link up with you again because you pulled the rug out in front of her. Another date will be in the books. But let’s be real, if she’s only downing one drink, she wants out 99% of the time.

Did she ever reference the future?

If she ever references the future in your conversations with you in it, whether it being a restaurant she says you have to try, ideas for activities she wants to do, movies she think you need to see or anything at all. She’s into it.

If she never referenced the future and skirted around it anytime it came up, then don’t bother.

Did she flirt for real?

How to tell if a girl is flirting for real? Easy: consistency and follow-through. Let’s tackle consistency first, if she’s thinking of you with your shirt off she’s not only going to get closer to you but also make sure she’s the only girl basking in your manly attention. She does this with CONSTANT reminders — casually touching your arm or solid eye contact combined with a smile she will be dropping subtle hints all the time. Women like to mark their territory, be on the lookout.

However, some women naturally engage in a lot of eye contact. It doesn’t always signify they are feeling the D. A good way to double check if her eye contact means interest is check where she is looking.  Where do her eyes go when there is a break in conversation? The waiter? The TV? People watching?

Women think about sex just like men do, if she’s feeling it she’s gonna be checking you out. Tracing your body up and down. If she is distracted and not looking at you during conversation pauses, the eye contact may just be politeness on her part and not interest.

Is she interested in post date texting or conversations?

After consistency we have  follow-through. This so important, that even if she was hitting the consistency button like hot cakes during the date but it is not coupled with follow through, then you’re probably SOL.

Maybe the date lasted for a few hours, her body language was engaging, she touched you, she had eye contact, referenced the future  and you even snuck in a make-out session, but after the fact she goes dark. Or maybe she becomes really sparse in her communication. She’s not into the D as much as you’d like to think she’s into the D.

Women like first dates, they stress over second dates. They start going deep into their head playing out simulations of the future that are usually not even close to the realm of possibility. She’s stressing about expectations, wondering if you are expecting sex, if she will like your friends, if you will end up not liking her etc etc. The list goes on and on.

There is a good chance she went full headcase and that’s why she’s gone dark. If this is the case, you don’t want a headcase, if not then she just used you for a fun date, some lip action but never intended on taking you seriously.

Either way, move on.

best questions to ask a girl

Observe, Question, and Listen

Take extra notice on how she speaks about other dates and exes. This may be your first clue to whether you’re on a date with a legitimate crazy bitch, or a dope – ass female who is going to make your pre-teen fantasizes a reality. Plus it gives you context on her perception of men and dating. This can be crucial in formulating new question and gauging interest.

Focus on is frequency of meetings. Back to the consistency and follow up. Over the course of the next few dates and texting, take notice of both of these.

How she interacts with other people is arguably more important than how she interacts with you. Everybody is on their best behavior when dating starts. She is only going to let you see her best side. But often when around their friends or others you can get a preliminary sneak peek on how they really are by watching them interact with others

Plus it can be used to gauge how much interest she has in you, If she likes you she is going to treat your peers and anyone in your social circle very well. If she’s an ass to your friends right off that bat, she’s not that into it.

So get out there and start preparing, get a pair of ovaries in front of you and start practicing. Whats stopping you? Now that you have all the knowledge you need. (hint it’s fear)

Make your own luck assholes. Signing out.

About Johhny Cage