/  Dating

69 Interesting Things to Talk About With Your Crush

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Joshua Sigafus

Dating, Relationships

Joshua has 15 years of writing experience within the complex territories of dating, masculinity, and relationships. His own personal life journey was kick-started by a pivotal marital breakdown of his own and led him down a path of self-discovery and masculine transformation, culminating in him developing a career as a men's dating coach. Read full bio.

Last Updated: Feb 11, 2024
18 min read
Things to Talk About With Your Crush Man and girl on date with girl laughing at mans gesture

I once matched with this super cute woman on a dating app. 

At this point in my life, I was freshly separated from my ex-wife—and I was a complete train wreck. 

But hey, I was trying my best. I even bought a new shirt just for the occasion. 

We met up, and she was actually even hotter than she looked in her pictures. 

(A somewhat rare occurrence, am I right?)

Well, I started stumbling through the date with my foot placed squarely in my mouth. 

In the span of the first 30 minutes, I made several vital mistakes that, looking back on it, now make me cringe with unspeakable horror: 

  • I only talked about myself
  • I ‘bragged’ that my shirt was brand new
  • I vented for a hot minute about the sadness of my marriage falling apart
  • I told her that I’d date her, and that ‘I’d like it’ if she were my girlfriend

Ooft. It wasn’t pretty. 

Ironically, she opened up about some pretty weird stuff as well. 

“I’ll be honest, I’m not really into men. But I’m trying to force myself to be straight because every lesbian I’ve dated has been abusive and psychotic. I have a lot of other baggage as well that I’m not going to share until I’m sure that I’ve found the right person.” 

No cap. I swear, I’m not lying about this stuff. (I guess I’ve had an interesting dating history, eh?) 

This date didn’t end up going so well. 

But it served as a valuable (if painful) learning experience for me on my journey to understand women, learn how to date, and just in general navigate the wild-west world of the dating marketplace. 

And it goes without saying—had I had a better idea of what types of things to talk about with a crush (i.e. the woman you’re interested in, getting to know, and vetting as a potential partner), this date may not have turned out as terribly as it did. 

When it comes to finding topics to talk with a romantic interest about, it’s really important to focus on the primary objectives:

  1. Getting to know her
  2. Building connection
  3. Vetting
  4. Creating emotional impact
  5. Escalating

So in this post, you’re going to learn about some topics that you can talk to your crush about—without doing what I did (awkwardly saying all the wrong things at all the wrong times). 

For the most part, these topics (when used correctly) are golden for almost any type of dating scenario. 

Note: Keep in mind that if you really do have a crush on this woman, you’ll want to avoid succumbing to oneitis. Brush up on the topic with this guide: Oneitis: How to Stop the Obsession and Level Up Your Mindset

It also wouldn’t hurt for you to do a quick refresher on ‘attraction brain chemistry.’ For that, consider grabbing a copy of Helen Fisher’s amazing work on the subject: Why We Love: The Nature and Chemistry of Romantic Love

Alright. Now let’s dive into it. 

Focus On These 21 Topics First

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1. What Kind of Person She Is

You can never go wrong asking a woman about herself.

This is valuable because when a woman describes herself to you, she’ll give you clues about how she perceives herself.

This is often going to provide you with valuable information that you can use to either ask more strategic questions, or to get a sense of what her relationship with herself is like. 

2. Past Dating History

This is technically a form of hardballing, but I 100% believe in it. Don’t be afraid to ask her about her dating and relationship history.

This helps you to weed out women who blame all of their failed past relationships on their exes. That’s a red flag you’ll want to avoid.  

3. What She Does for a Living

Don’t stay on this topic for too long. But it’s a must-ask because it’s an important general thing to learn about someone who could potentially end up being an intimate partner.

Plus, it gives her a chance to talk about herself in an area that she’s probably relatively confident in—and that’s good for bringing out some of her inner confidence and seeing her in a more ‘comfortable’ element.  

4. Her Childhood

This is a great topic because it can bring up emotional memories, which is awesome for creating emotional impact. 

(Learn more about how to create emotional impact by reading my personal favorite book about seduction and pickup—The Noble Art of Seducing Women: My Foolproof Guide to Pulling Any Woman You Want, by Kezia Noble.) 

5. Spirituality

Don’t argue about the existence of god. But DO ask her what her spiritual beliefs are. Listen and learn about her. 

6. Hobbies and Interests

Knowing what someone does for fun in their spare time is important in a dating context because it can reveal potential compatibility overlap—which is great for connection. 

7. Personality Type

Ask her what her Myers Briggs and/or Enneagram personality types are, and share yours with her. 

8. The Zodiac

You may or may not be into this, but women these days are pretty hardcore about it. At the very least, it’s fun to watch them Google your sign to see if you’re compatible. 

9. Upsides and Downsides

Ask her to give you an overview of her ‘pros and cons’ as a human. At first, this is kind of a comical question. But ironically, it can also lead to some deep conversation. 

10. Overcoming Challenges

Discussing the challenges you’ve both had to overcome in life can create opportunities for emotional engagement and impact.

Plus, it’s a great idea to know where this person is coming from in a ‘life experience’ context. 

11. Favorite Movie, and Why

Who doesn’t love to talk about movies? 

(Not a movie buff? Here’s our must-watch list to get you started.) 

12. Favorite Music

Looking at someone’s Spotify playlist will reveal almost as much about them as their browser history. 

(Ok, that’s not true. But it’s a close third.) 

13. Favorite Food

Learn what her tastebuds are like. This can also give you ideas for a second date (if she proves to be a high value woman who’s worth your time.) 

14. Her Political Views

Don’t get into an argument over this. Listen to learn, observe, and see if the two of you are in any way compatible. 

15. Her Views on Family

If you want a family, it’s in your best interest to find out where she stands on the issue. This is a super-important point of future compatibility. 

16. Future Goals and Plans

Does she have goals and plans for the future? If so, do they align with yours?

17. Traveling

Traveling is literally good for you—in a myriad of different ways. 

And talking about it over dinner with your crush is a great way to incorporate feelings of adventure and discovery without ever leaving the restaurant.  

If you haven’t done a lot of traveling, this list can get your imagination fired up: 28 Places Every Man Should Visit In His Lifetime

18. Deal Breakers

What are her deal-breakers in a relationship, and what are yours?

This is an excellent topic to discuss. It can quickly reveal whether or not the two of you have compatible standards, and can contribute to a lot of connecting over those compatibilities. 

19. Quirks

Ask her what her quirks are. Another fun way to approach this is to guess each other’s quirks. This can be hilarious. But also, women love it when men take such an intimate interest in them. 

20. Lifestyle

What kind of lifestyle does she want to live? And are the two of you compatible in this area? 

This is more important than a lot of men realize because it’s actually high-key stressful to try to have a relationship with someone who’s accustomed to a totally different lifestyle than you. 

Plus, it’s a great discussion to have either in-passing, while hanging out, or even over dinner. 

21. Heroes and Thought Mentors 

Does she have any thought-mentors or real-life heroes whom she admires? This can give you some keen insight into her value systems—but it can also let you in on whether or not she’s wise enough to look up to (and learn from) highly successful and exceptional people.  

48 More Good Things to Talk About With Your Crush

Kezia Noble Quote

These topics are great for more specific types of situations. 

They’ll give you some great stuff to talk about in a range of different contexts. 

Note: You’re getting inside access to the real stuff I talk to women about here. These aren’t cookie-cutter topics. I’ve used every single of these at some point in time—and they work. Use them well, and you’ll get great results.

Over Text

Keep in mind that texting is a subtle game—especially when it’s with a woman you’re crushing on. 

To brush up on your texting skills, consult this in-depth guide: How to Text a Girl: 35 Texts That Will Make Her Want You

1. Date Plans

If you’ve moved the conversation over to text after getting her number, congratulations! Now it’s time to set up the date

2. Logistics

In most cases, you don’t want to be too long-winded over text. It’s better to save those conversations for having in-person (preferably while cuddling after some bedroom gymnastics). 

With that being said, texting works wonders as a way to communicate logistics. 

“I’ll pick you up at 7:00. That’ll save you from needing to pay for an Uber.” 

On the subject of ghosting: Uh oh! If you get the feeling that she may be ghosting you, don’t panic and start double or triple texting. Consult this guide, and follow the steps to get it handled.

3. Quick Questions

Sometimes, engaging in a bit of short-form conversation over text is a great way to build connection between dates. 

Have you come up with a quick, not-too-serious question you’d like to ask her—to satisfy your own curiosity? Fire away. 

4. Confirmations

If she texts you some kind of detail, either regarding plans for later or just to chat, it’s usually in your best interest to respond in a timely fashion with a confirmation that you’ve gotten her message. 

If you wait too long to reply, she may get the impression that you’re not that interested.

Sometimes this can work in your favor, such as when you’re engaging a bit of competition anxiety to up the ante. 

But be careful with this, as it’s a technique that can also backfire if not performed correctly. 

5. Things That Remind You of Her

An unexpected text containing a little story, a picture, or a meme that reminds you of her can be a great way to build some extra connection, brighten her day, and make her think of you in a pleasant way. 

6. Post-Date Questions

One technique that I sometimes use to build connection between dates is this:

The day after the date, I’ll text her some version of this message:

“Hey, I had a great time last night! I was also thinking about XYZ thing we talked about, and it made me curious about something.” 

Then, I’ll let it sit for about 15 minutes—just to let the anxiety creep up on her a little bit.

Then I’ll send the second half, which constitutes some kind of question I thought of that I never got to ask her during our date. 

I try to make this question as thought-provoking, interesting, and personal as possible. 

It gets ‘em every time. 

7. Daily Snap-Shots

I’m not a fan of sending these first. 

I prefer for these types of texts to be in response when she texts you first. 

But sending little snap-shot snippets of how your day is going can make you sound interesting, busy, and high-value (if you word them correctly). 

On the Phone

kezia noble quote approval

1. The Events of the Day

Phone conversations are an often underutilized way to build more connection between dates. Consider giving her a call instead of responding to a text message if texting just isn’t super convenient at that moment. 

I sometimes do this if I get a text while I’m driving—and lightheartedly discussing the events of the day is a great place to start. 

2. Victories and Failures

For those longer late-night phone conversations, ask her about the victories and failures she experienced that day. 

These types of conversations can be very intimate. 

3. Upcoming Plans for the Week

Asking her what she’s got planned for the week can be a great way to gauge how open she may be to a future date. 

4. Personal History

Getting her to open up a bit about her personal history can help you to learn more about the real person behind the ‘everyday persona.’ 

Plus, this creates a prime opportunity to create emotional impact and attachment. 

5. Hopes and Aspirations

What are her hopes for the future?

Does she have aspirations that she’s trying to work toward in life?

These are very meaningful topics that can spur some excellent phone conversations. 

6. Fears and Challenges 

What is she afraid of in life? 

What types of challenges does she tend to face on a regular basis? 

Asking these types of questions can prompt her to open up—facilitating a deeper connection while also giving you some additional information about her inner workings as a woman. 

7. Stories from High School

Taking turns sharing stories from high school can be really fun and comical. 

But it can also give you some insight into the ‘grown-up high schooler’ living within the woman you’re interested in. 

Hey—we’re all a product of our formative years to some degree, right? 

Flirty Things

dont be afraid to talk to her quote

Flirting is a powerful technique that can help you to escalate with the woman you’re interested in. 

But before stumbling blindly into the ‘live fire’ zone, read through this guide to help you with your teasing technique.

And if you’re truly serious about leveling up your entire dating game end-to-end, I highly recommend you check out my new Dating & Masculinity Transformation Package.

Want better results with women?
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This premium step-by-step system will teach you everything you need to know to attract the women you desire and keep them in your life. Across 13+ hours of engaging video lessons and 300+ pages of eBook content, renowned dating coach Joshua K. Sigafus will teach you the exact strategies that he and hundreds of his students have applied to achieve wildly positive results with women.

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1. Celebrity Crushes

Talking about celebrity crushes can start out fun and light-hearted. But it’s also a great vehicle to create the faint beginnings of some amazing sexual tension. 

2. Rating Your ‘Bedroom’ Skills 

Ask her to rate her bedroom skills. This is funny and a bit ridiculous—but it’s also obviously sexy. 

If you’re really bold, ask her to rate her skill level in various different types of acts. 

Just be careful to keep this one fun and light-hearted. You don’t want to give off creepy incel vibes

3. Intimate Desires

Are there some particular things she fancies after the lights get turned down for the evening? What types of things is she into? Ladies love to talk about this with men they’re interested in. 

4. Favorite Positions

This is obviously a classic fun conversation to have that can definitely turn flirty. Just remember to keep it chill, and not to give off those ‘thirsty guy’ vibes. 

5. Most Attractive Features

Rating each other’s most attractive (or if you’re even bolder, you could make it ‘most kissable’) features can be a great way to set the tone for ‘coming attractions’ later. 

6. Number-One Turn On

Build up to asking this question after you’ve already been heavily flirting for a while. It’ll give you some awesome insight into some of her deepest desires (and how seriously she takes them). 

7. Secret Fantasies

Every lady has a secret fantasy or two hidden away inside. 

You know what they say:

Inside every good girl is a naughty girl just waiting to come out for the right man.

I’ve found that this is 100% true. You just need to be alpha enough to bring it out of her. 

Interesting Things

1. Fascinating History

Who doesn’t love a bit of interesting history? 

2. Conspiracy Theories

I’ve found that nearly every lady has a conspiracy or two that she secretly believes. This makes for some pretty fun (and sometimes surprisingly deep and interesting) conversation. 

3. Ancient Religions

Discussing the history of religion is really fun, especially if she’s kind of a brainiac and/or a nerd about that kind of stuff. 

4. Aliens

Are we truly the only sentient life forms in the universe? If not—then how might our cosmic neighbors differ from or compare to us? 

And why haven’t they sought us out to make contact? (Or have they already?) 

5. Podcasts 

Podcasts are becoming extremely popular these days. 

Comparing notes on a few of your favorites can make for great conversation. 

6. Mythology

Similar to ancient religions, a lot of people are fascinated by ancient Greek, Roman, Norse, and Egyptian mythology. 

Just talking about the mythological epics alone can be a great way to pass the time. 

7. Intergender Dynamics

If you’re bold enough, ask her what she thinks about traditional gender roles and/or the relationship between the masculine and the feminine. 

Does she believe that we’re getting it right in our modern world? Or are we leaving some important things out of the equation?

(If you’re a real storm-trooper, you could even ask her about her views on modern feminism.)

Funny Things

1. Sexy Names

What are the sexiest male and female names?

This is a super fun question to compare notes on. 

2. WiFi Network Names

I once had a neighbor who named their WiFi FBI Surveillance Van. 

These stories are always fun to share. 

3. Awkward Experiences

Share some awkward experiences, then have her return the favor. 

4. Starting a Secret Society

If she was going to start a secret society, what would it be? 

5. Trashy vs. Classy

Ask her what she considers to be the definition of classy and trashy, and then ask her to give you examples. 

6. Annoying Songs

What is the most annoying song in the world? Compare notes and see if you agree or disagree. 

7. Embarrassing Stories

Everyone has a few embarrassing stories to tell. Go story-for-story to see who’s been in more embarrassing situations.

Deep Things

1. Is Truth Objective?

Swim in some deep philosophical territory together on this one. 

2. Is Anything Actually Real?

This one is pretty abstract. But some women love to talk about it. 

3. Are We Living in a Simulation?

Personally, this is one of my favorites. Run Nick Bostrum’s Simulation Hypothesis past her, and see what she thinks about it. 

4. What Are Humans Doing Right or Wrong?

A discussion about the human condition is always going to be deep and interesting. To prepare for this one, consider reading The Moral Arc: How Science Makes Us Better People, by Michael Shermer. 

5. What’s the Biggest Problem in the World?

Is it climate change? Pollution? Religious dogma? Nuclear war? Unmanageable viruses? Creepy male-centric Reddit threads? 

It’s up to the two of you to figure it out. 

6. Does Anything We Do Actually Matter?

This is a trippy one because it leads into some pretty wild philosophical spirals. If she’s a philosophy major, this will probably turn her on.  

7. Do We Actually Have Free Will?

This is one of my personal favorites. 

Skim through the classic book Free Will, by Sam Harris, in preparation for this one. 

Random Things

1. The Best Way to De-stress

How does she unwind and relax after a long day?

2. Words That Best Describe You

Ask her to pick 3 words that best describe you. Then, do the same for her. 

3. Tattoo Ideas

Everyone loves to talk about this one, right? Especially those high maintenance women

4. Your Theme Song

Choose theme songs and jam to them on the car stereo. 

5. What Animal You’d Ride as a Mount

To this day, I dare any woman to convince me that the best mount to ride in a fantasy-world setting wouldn’t be a dire (giant) silverback gorilla with full-plate armor.  

Come at me bro. 

6. Superpowers 

If you could choose any superpowers to have, what would they be—and why? 

7. Drinking Stories

Personally, I’m living my best sober life these days.

But I’ve got a collection of pretty mortifying drinking tales from my ‘drunker’ years—and from time to time, I’ll use them to regale and entertain whatever lady I happen to be passing time with. 


Hopefully, this post has helped you to fill your notebook with some awesome things to talk about with that lady you’ve had your eye on. 

One final tip—never forget to keep working on yourself as well. Remember—women are great. But there’s no substitute for continuing to become the best man you can be. 

It’ll increase your attraction. But it’ll also just make you happier overall. 

For more tips, tricks, and guidance, make sure to subscribe to our YouTube channel

Go with grace, and never give up your power.