If you’ve been looking for questions to ask your crush to get to know her better, look no further! I’m here to help you not just break, but SHATTER the ice with that lucky lady you’ve had your eye on.

Whether your crush is someone you’re about to go on a date with, someone you’ve already been out with, or a friend you want to avoid being friend-zoned by, these questions can be one way to help build a romantic connection.

Questions to Ask Your Crush

Question #1: What is Your Biggest Pet Peeve?

It’s best to find this out about your crush as quickly as possible, so you can make sure you avoid unknowingly getting on her nerves.

Question #2: How Would You Feel About a Dwayne “The Rock” Johnson Presidency? Hey, it Could Happen.

Something like this is a great way to lightheartedly introduce the topic of politics without getting political with your crush.

Question #3: What’s the Worst Job You’ve Ever Had?

We’ve all had some nightmare experiences when it comes to jobs. Enjoy commiserating over your past employment woes and then continue the conversation by asking…

Question #4: What is Your Dream job?

If she’s already living the dream, ask her what she first wanted to be when she was a kid?

Question #5: If You Could Have Dinner With One Famous Person (Alive or Dead) Who Would It Be and Why?

This can also be a great way to keep the conversation going and transition into topics like your favorite actors, movies, and so on.

Question #6: What Is One Topic of Conversation You Avoid at All Costs?

Like the pet peeve question, this gives you an idea of what YOU should avoid talking about. It also gives you more insight into her personality.

Question #7: Can Money Buy Happiness, or Was J. Lo Correct When She Said That Love Don’t Cost a Thing?

This is a good way for you and your crush to have a more pensive discussion, while also making her laugh with the mention of that J. Lo throwback jam.

Question #8: What Is Your Top Dating Deal Breaker?

Obviously, this is a good way for you and your crush to understand what sort of boundaries should never get crossed in case you begin dating or get more serious.

FYI, your crush may not mention this VERY IMPORTANT deal breaker, so I will.

In a recent interview, actress Kaley Cuoco mentioned one of her biggest dating deal breakers is someone being a bad tipper. She described going out to dinner with another famous actor who — despite a bountiful income — left an EXTREMELY meager tip for the waiter at the end of the date.

You don’t need to be rolling in dough to leave a nice tip for your waiter or bartender at the end of a date. And in case you’re wondering, between 15 and 20% is the amount you should tip (with 15% being average service and 20% is excellent).

Question #9: What’s the Most Embarrassing Moment You’ve Had Recently?

You can also share your own embarrassing moment. This helps you both break the ice and not take things so seriously, which can also alleviate nerves.

Question #10: What’s the Most Exotic Place You’ve Ever Been To?

This is a great way to either swap stories about your travels or as a way to talk about the places you dream of visiting.

Question #11: Where Do You See Yourself in Five Years?

This is a great way to learn more about your crush and also show that you encourage her ambitions.

Question #12: Are You a Fan of Monogamy?

Recent generations have placed less emphasis on monogamous relationships, and there has been growing acceptance of keeping things casual and engaging in polyamory.

As long as things are consensual, it’s all well and good. However, if you’re looking for a long-term partner, you want to know up front what her feelings are on monogamy. This is also a good opportunity for you to let her know that you’re a fan of commitment, which will make her feel safer with you.

Question #13: What Was Your Best and Worst Kiss?

Not only does this help you understand how she likes to be kissed, this type of flirtation during a date can put her in the mood.

Question #14: Would You Like a Shoulder Massage?

ALWAYS!

Now, reserve something like this for when you two have established a mutual attraction, and don’t just go about rubbing her shoulders in a crowded restaurant — that’s just awkward.

Question #15: What Were You Like as a Kid?

Even the most seemingly perfect people had their awkward phases. Learning about your crush back before the days of online dating, smartphones and general adult responsibilities can help you get to know her better and, thus, be less intimidated.

Question #16: What’s the Worst First Date You’ve Ever Been On?

This can be posed as a purely curious question while also giving you access to a list of things NOT to do when on a date with your crush.

Question #17: What Is the Best Drink And/Or Meal You’ve Ever Had?

Come prepared when asking this one! This is a great question to ask whether you have NO IDEA whether your crush reciprocates your feelings, you two have established there is a mutual attraction there, or if you’re on a first date. Before fielding this question, be sure you have one of your favorite bars or restaurants in mind so you can wax poetic about your favorite menu items. As the conversation flows, you can squeeze in an invitation so she can see what all the (your) fuss is about for herself.

Question #18: What Do You Like to Do in Your Free Time?

Again, this is one of those questions to ask your crush that can lead to an invitation for a first or second date.

Discovering what your crush likes to do in her free time can also help you see if you have common interests.

Question #19: If You Won the Lottery, What Would You Do With the Money?

“SPEND IT ON MYSELF AND NO ONE ELSE!” she replied emphatically.

Oh…

As you can see, questions like this can let you know whether your crush is kind-hearted and charitable, or if she is a bit too superficial for your taste.

Question #20: If You Could Only Eat One Thing for the Rest of Your Life, What Would it Be?

Yes, this is another food question. Why? Because a girl’s gotta eat, and if said girl is someone you’re attracted to, you’d best be making moves to be the one sitting across from her come meal time.

Question #21: Do You Believe in Astrology?

This puts a spin on the hackneyed “what’s your sign?” line. Regardless of your thoughts on zodiac signs and the roles it can play in compatibility, astrology can still be fun to think about and this is a great conversation starter.

Do a bit of reading up on astrology before asking this question. It may turn out that your signs are supposedly “compatible” and that can be a fun and flirty way to keep the conversation going.

Question #22: What Are Your Thoughts on Brunch?

Because the best types of bloody marys and mimosas are bottomless.

Question #23: What did you honestly think of La La Land?

There’s only a 99.99% that she’s seen it, but I think asking this is worth the risk.

Question #24: Can I walk you to your car?

This gives you an opportunity to keep the conversation going a little longer and also shows that your chivalrous. And guys, let me tell you, no matter what year it is, chivalry is one thing that never goes out of style.

Question #25: Are You Free Next Saturday at 1pm for a Hike?

Always secure a second date while on the first. Always secure the third date while on the second. You get the point. Even more specific, make sure you secure a specific time, date, and location for your next date. This is what I call a TDL. Women love a man who can commit. 

Practice Makes Perfect

Having a crush can leave you equal parts exhilarated and stressed. It’s important to remember that, if you are focusing on only one person during the early stages of dating, you can be more prone to idealization.

Idealization occurs when everything about your crush seems absolutely amazing. Maybe you can’t even picture dating another woman because the picture you’ve developed of your crush is at some sort of unachievable standard. Remember that no one is perfect, and that includes your crush.

Having a crush can lead to feelings of infatuation, which can release all sorts of chemicals in the brain that make you feel giddy one minute, and (if your crush doesn’t reciprocate your feelings) agonized the next.

One way to avoid this rollercoaster is through MegaDating. Rather than pine after one person, megadating is a strategy where you date several people at once in order to reduce anxiety and see that the old adage about their being “tons of fish in the sea” is much more than a simple cliche.

As a dating coach and matchmaker, my job is to help people get the most out of their dating lives and eventually find long-term relationships.

Want to learn more? Visit my calendar and book a New Client Zoom session with me today. During our intro session we’ll diagnose your dating life, create an action plan, and see if my coaching or matchmaking programs could help you reach your dating goals this year!

I look forward to working with you!