Day: January 27, 2022

Are you looking for the best first date questions to ask a woman on an upcoming date?

Smart guy.

The first three dates are crucial to long-term romantic success.

First impressions are so important in fact that you’re going to want to make sure you come prepared.

You’ll need to have a solid list of first date questions to ask that don’t make her feel like she’s in an interview (but don’t be afraid of a little silence either).

Flirty Tip:

A first date is also an opportune time to learn more about what activities she’s always wanted to try but never has.

This probing curiosity offers you the ability to seamlessly suggest a compelling second date activity that she’s bound to say “yes” to. It also sets you apart from other men she’s dating who haven’t learned to ask meaningful questions or listened to her answers — powerful stuff for converting a first date into a second date.

The following questions to ask a woman on a first date are designed for a typical first date.

I’m assuming that you don’t know this person very well, which is why I included a lot of background questions.

However, if you happen to be going on a date with someone you already know, I have you covered there too. Check out my article on What to Talk About on a Date If You Already Know the Person.

Why Do Good First Date Questions Matter?

The quickest way to win someone’s affection is by showing an interest in what they’ve got to say. We most often do this by asking revealing questions and listening intently to the answers. A happy byproduct of asking questions is that we’re able to quickly evaluate whether this person is compatible with you or if you should swipe on to the next one. 

Along with the benefit of quick evaluation the quality of your conversation will also set you apart from the competition.

If you ask the same questions as everyone else or stay too on the surface, the relationship won’t escalate and you won’t win another date. But, if your questions evoke emotional responses with depth and vulnerability, you’ll be that much closer to moving to the next date (aka round two).

And now without further adieu, take a look a look below for the top 25 first date questions to ask a woman on a date.

Questions To Ask A Woman On A First Date

Question #1: What is Your Favorite…?

Ask her about some of her favorite things and use them to fuel your future date plans. Favorites can include:

• Favorite food: Use this for restaurant planning on the third date. 
• Favorite animal: If she likes cats and dogs, maybe take her to a cat cafe (if you live near one), take her or your dog to a dog park, or volunteer at a local animal shelter. If she likes ducks, go for a walk near a pond where you can feed ducks for your second date. If she loves horses, horseback riding could be a future date plan, and so on.
• Favorite Author: This is a great question is general, but also particularly enjoyable for sapiosexuals.
• Favorite movie: You can piggyback off of this question by seeing what types of movie genres she tends to enjoy, and plan a movie date based around that. This could be useful when trying to get her back to your place after dinner on a third date.
• Favorite sports team: Perhaps you use this to your advantage when planning a physically active second date. Maybe you attend a tailgate party for her favorite college team or arrange a third date at a bar that caters to fans of that specific team.
• Favorite band: Like her favorite movie, pay attention to the genre of music. You can use this to create a Pandora or Spotify channel with similar artists. Have this playing in the car when you pick her up for a date. Turn on this station at your home when she comes by after dinner on a third date. The familiarity of the music she likes will set her at ease and make her feel good about you too. 

#2: What’s Your Best Childhood Memory?

This is a nostalgic first date question that can be a great way to open up more dialogue and build intimacy. Research shows that nostalgia can boost mood and decrease stress. 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 festival or carnival. Planning a nostalgic-date activity is an uber-powerful way to connect to her deeply on an emotional level.

#3: Are You a Morning Person or a Night Owl?

Again this can give you an indication of the types of dates you want to go on, and whether or not you want to plan something like a morning hike or a dance party/club that keeps you up until 2-4 am.

Determining whether you share similar wake-sleep cycles can help determine compatibility. Do you want a partner who likes to sleep when you’re wide awake?

#4: How Many Siblings Do You Have? 

Find out how many siblings she has and, to keep the conversation going, share how many you have, or if you’re an only child. If you have any light-hearted stories about your sibling dynamic or being an only child, that can also help to break the ice.

Don’t be afraid of penetrating the surface level of your conversations. Asking emotional questions, rather than logical ones (like “what do you do for work”) is key to your dating success.

Romantic attraction is about sensation and emotion, not logic. Don’t be afraid to get to know her. I’d even push the envelope further and ask her who her favorite sibling is. Eliciting emotional responses are critical for avoiding the friend zone.

#5: What Would Constitute a “Perfect” Day For You?

Depending on how doable their perfect day is (i.e., if it involves cliff diving in Rome followed by dinner in Paris, this won’t count as a realistic third date), you can try to recreate that — or at least elements of it — during future dates.

I also like this question because it provides insight into how she sees the world and what’s most important to her. Pay attention to the answer she gives you and take notes immediately following the date so you can remember and use what she’s told you. You also want to ensure that you have a solid answer prepared for the questions you ask.

Often, she won’t know what to say on the spot and will flip the table on you. She might say something like, “I don’t know, that’s a hard one, how about you?” In this case, you’ll want to be well-versed in storytelling so that you can create a visual representation of your perfect day in her mind.

#6: What Hobbies Would You Like to Get Into If You Had the Time and Money?

This question offers a creative spin on the “what are your hobbies” first date question. It’s an excellent way for both of you to talk about what you’d like to get more into in the future, discover if you have particular aspirations in common, and try to use these ideas during future dates.

This question is especially powerful for crafting compelling second date ideas. If a woman expresses interest in doing a specific activity or hobby but has some reason for never having tried it, that’s an easy way of getting her to agree to a second date. Suggest that the two of you do that hobby on a specific day and time. It’s a lot easier to get her to say “yes,” if she’s the one who offered up the idea.

If her hobby is too pricey for a second date, try and use components of it that are related to crafting a realistic and exciting second date. For instance, I’ve always wanted to try kite-boarding, but to do so on a second date would cost upwards of $200. Not exactly feasible.

But if a guy I was dating suggested that we grab a bottle of wine on Friday and head out to the beach to watch the kite surfers in action, that’d be a no-brainer for me.

Question #7: What’s the Last TV Show You Binged or Re-Watched?

If you both happen to be fans of a quotable series, this is an excellent way to bond. It’s always interesting to see if you share favorite shows or movies because it reveals a lot about your interests, values, and perspective on life. For instance, I doubt I’d have much in common with a guy who said his favorite show was something on the cooking network because I suck at cooking.

Perhaps it would be valuable for a guy who loves cooking to know he’s on a date with a woman who hates it. This realization might suggest that he recalibrate his search in the hopes of finding a more compatible woman.

Alternatively, perhaps it would be an exciting opportunity for him to show the woman why cooking shows so compel him. That passion could spread to her and breed an interest she never previously explored.

Funny First Date Questions #8: What Is Your Spirit Animal?

You might have to follow this question up with, “just say the first animal that pops into your head.” This question offers a fun exercise to see how the woman you’re on a date with views herself. For instance, when asked this question myself, I spontaneously answered “pig” but didn’t know why.

The next apparent questions was, “why do you think a pig popped into your head?” To which I answered, “well pigs are cool, they’re short and fat, and smart.” After googling the meaning of having a spirit animal as a pig, I learned that pigs represent luck and money (think piggy banks) and that they’re super emotional and loving. Sounds like the perfect spirit animal to me.

Ask your friends this question, too; the diversity of answers is fascinating. What’s fun about this question is that it reveals so much. Just think how you would answer it? Are you a tiger and if so, why?

Are you a cheetah, an owl, a lizard, a banana slug? It’s fun to think about and super unique to ask someone. Asking what a woman’s spirit animal is, can be a playful way to stimulate a fun, and exciting conversation.

Funny first date questions such as this one show her you’re fun to be around. That might just be enough to score a second date.

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

When someone is a good tipper (i.e., they believe in tipping a minimum of 18-20%), that can be an indicator of generosity. And generous people tend to make the best partners.

As someone who used to work in restaurants, I love this question because it reveals much more than whether a person is generous. It also tells a story about humility, empathy, value, and finances. If a man I dated didn’t tip someone well, or if they treated a server poorly, I was 100% out.

Flirty First Date Questions #10: What’s Your Biggest Pet Peeve?

It’s good to learn this early on so you can avoid unintentionally irking her. Plus, it’s funny. People have the silliest pet peeves and drilling down into why that particular nuisance bothers them so much, can lead to lots of laughter.

Comedians do this all the time when they rant about random occurrences in their life. It’s funny, and anytime you can laugh with your date, you’re much more likely to see her for a second date.

You also want to develop your own pet peeve story. I attended a stand-up comedy class where the teacher had us do this as an exercise. He said that we should use our recording apps on our phones and spend 10 minutes ranting about something that annoyed us each day.

Then, he advised us to listen back and pick out anything randomly funny to use as a one-liner or to develop a bit from. Sure there was loads of material that wasn’t particularly funny, but there was also a lot that was. You can do the same to glean out a super amusing response to this question on your dates.

What Can Good First Date Questions For A Woman Tell You About Your Date?

The right question can qualify a potential match in or out.

Asking a question that reveals whether they share the same values, goals, motivations, hobbies, and favorite things (food, travel destinations, musical preferences) reveals deep compatibility. If you ask someone what their go-to comfort food is, and they say salad, whereas yours is pizza, that may be a compatibility issue down the line when you both have a bad day and want different things to soothe yourself. It may sound trivial but seeking out such compatibility early on speaks to the long-term potential of the relationship.

Also, ask follow-up questions.

Questions that come out of the blue can be off-putting and signal that what you were previously talking about wasn’t interesting enough to further delve into.

The best questions are organic and follow-up on something you two are already talking about. This shows you’re genuinely interested in what she’s saying and who she is.

Question #11: Where Are You From Originally?

This question has the potential to open up deeper conversation channels. She may have lived somewhere abroad or done a lot of traveling throughout her life. If she answers with something like, “I’m born and raised right here,” then try asking her where she’d move if she had unlimited money.

If you learn that the woman you’re on a date with is from somewhere very different, then ask her what it was like to grow up there. What did she eat? How big was her school? Where any of the laws or customs super different? This topic can lead you down many exciting conversational paths and can provide a rich, cultural experience for you to explore as well.

Question #12: What Did You Study In School?

I’d avoid trying to figure out a woman’s labels or social standing by asking her where she went to school. Doing so is an egotistical attempt at measuring her self-worth, but it’s false and has nothing to do with love. Rather than asking a common question like, “where’d you go to school,” try asking her what she studied.

The topic a woman chooses to spend four years or more studying will reveal much more about her values and motivations. Plus, asking a woman where she went, as opposed to what she cared about while she was there, is less emotionally compelling and a lot more douchey.

Why would you want to know where she went? So you can compare who is smarter? Let the status stuff go and dig into what she cares about, not how reputable her institution was. People do that to compare egos, avoid it like the plague. If she didn’t go to college, move on to the next question.

Question #13: What Did You Want To Be When You Grew Up?

Do yourself a favor and avoid the banal topic of what each of you does for work. Work-talk is a no-no in dating. Not everyone likes what they do, so bringing it up on a date isn’t a good idea. Even if you both enjoy your jobs, I recommend that you avoid talking about it on a date because it’s too logical.

Physical attraction is about sensation and emotion, not logic. Avoid discussing topical subjects that have little or no connection to feelings or emotions. That said, asking what she first wanted to be when she grew up, elicits nostalgic responses deeply connected to her senses.

It’s cute to remember what we wanted to be when we were kids. Thinking back on our thought-processes as young people reminds us of how innocent and young we used to be. Nostalgia always makes people feel good, and if she’s feeling good because you’ve asked her a nostalgic question, she’ll subconsciously associate you with that good feeling.

You could also try asking imaginative questions like, “What’s your dream job,” or “What type of business would you create if you had unlimited resources?”

First Date Questions #14: What is Your Favorite Alcoholic and Non-Alcoholic Drink?

This is another one of my favorite questions to get to know someone on a first date because it can give you fuel for the third date. One strategy for moving things back to your place after a third date involves mentioning a “rare drink” that you know how to make and think she should try.

You can use the types of drinks she says she likes during this date to give you some ideas for the kind of ingredients you’ll need for the third date drink.

Need ideas? Check out Buzzfeed’s 11 Unusual Drinks That Will Up Your Cocktail Game and these three-ingredient drinks from Serious Eats.

Question #15: Name Your #1 Bucket List Travel Destination

A person’s #1 bucket list travel destination might lead to more in-depth conversations about your date’s cultural heritage or family origins. Talking about preferred travel destinations sheds light into the kinds of climates your date prefers.

For instance, you might realize that you hate the idea of traveling to the colder areas, like Alaska, that she seems to love. Talking about travel can also reveal information about how open she is to new experiences. Ask her whether she would eat bugs in Thailand and you’ll know whether she’s as adventurous as she said on her profile.

Note: If you’re a big traveler and find out she’s a homebody, it might be doomed from the start.

Question #16: How Would Your Friends Describe You?

This question is a great way to learn more about someone and also reveal potential red flags. It would make sense for her to take this opportunity to say some nice things about herself and chat more about her friendships.

But for people who are challenging to get along with or suffer from things like an antisocial personality disorder, friends can be few and far between. Pay attention to her reaction to this question.

It shouldn’t be something that makes her angry, defensive, or super secretive, but if any of those things happen, it could be a red flag.

Question #17: What Do You Do for Fun?

I love this question. Fun is the key word and reveals an emotional answer. Whatever she says should be remembered and written down for future date ideas. Plus, it’s the most straightforward question in the world to remember.

The last thing you want to do on your date is to memorize a bunch of questions and recite them one-by-one, like a robot. Find 1-3 that resonate with you, and ask those. Dating shouldn’t feel like an interview.

What do you want to know and what’s the most straightforward question you can ask that will reveal it. That’s the question you should remember and use on every date you go on. For me, it’s this one.

Question #18: What’s Your Favorite Restaurant?

What’s your favorite restaurant, is a great first date question to have answered should the two of you end up on a third date. The third date is when I recommend taking a woman to dinner. For reference, here is how I tell my clients to structure the first three dates typically:

First date:

Choose something casual like a coffee, tea, boba, or chocolate tasting that won’t cost more than $10. Limit the date time to no more than an hour. Here are some additional first date tips.

Second date:

Choose something that costs no money and is physically active that takes place during the daytime. Here are a few examples of what would be appropriate for a second date:

• Go hiking
• Visit a museum
• Have a picnic at the beach or a local park
• Go on a brewery tour
• Find a free concert
• Sample foods at a farmers market

Here are some additional second date tips.

Third date:

The third date is where you can pull out all the stops for a romantic dinner. The third date also tends to be a time where you can seal the deal if it feels right and she’s interested.

You can read a complete breakdown of how to get your date in the mood by clicking here.

#19: What’s The Last Song You Played On Spotify?

You certainly don’t need to have the same musical interests to be romantically compatible. However, this is just one more question that opens up channels of conversation that can bring the two of you closer.

Plus, if she has a particular genre or band she’s crazy about, you can use this information to find a music venue or concert in your area that she would enjoy.

#20: Do You Think Goldfish Make Good Pets?

Yes, this may seem a bit random, but randomness has its perks. People often describe themselves as “cat people” or “dog people.” But what about goldfish? Does she consider them to be misunderstood?

Has she bonded with a goldfish? Or does she view this species as interior decor that requires feeding? The routes you can go in this goldfish conversation are endless.

#21: On Thursday Night I’m Going to the California Academy of Sciences Exhibit To See Leopard Sharks. Be My Date?

Lock it down. If you’re into the girl and want to see her again, secure the second date while you’re on the first.

Flirty First Date Questions #22: What Kind Of Trouble Did You Get Into Last Saturday?”

This is a remix of the classic question, “what do you like to do during your free time.”

When people ask the latter, they tend to receive a litany of one-word answers. Asking them specifically what they did last Saturday doesn’t allow your date to tell you what they want you to hear or present the best version of themself. Instead, you’re receiving a revealing and truthful account of their life.

Ask follow-up questions to signal your interest. 

Flirty Dates Questions #23: Wanna Look At Each Other’s Spotify Accounts To See If We’re Compatible?”

Again, another updated take on the classic (and much more boring questions) “what music do you like?” Spotify has a great new feature called Blend, that will even tell you how compatible your music tastes are and will create a playlist that includes music you both like. 

Question #24: What Was The Last Song You Belted When No One Else Was Around? 

This is one of the best questions to ask on a date because it asks permission to see her at her most intimate. There’s a reason she both sang it alone and belted it. Most likely she’ll give you a funny response and you two can have a laugh. 

This is an innocuous question that will gently peel back the layers – I hope you enjoy what you find.

Question #25: Do You Have Any Nicknames?

Only those close to her call her by her nickname.

Using her nickname automatically will make her feel comfortable around you and will create a warm atmosphere. 

Question #26: What’s Your Low-Key Superpower? 

Chances are she’ll say something that you two can both laugh at.

Something like, “I always choose something to watch on Netflix in under 3 minutes” or “I brush and floss twice a day, every day.” Guaranteed this question will produce a giggle or two. 

First Date Questions to Ask a Woman: Wrap-up

You are now equipped with plenty of questions to ask a girl on a first date.

But what if you’re having trouble even GETTING to that first date?

If you’ve found yourself in a dating rut, I’m here to help.

In 2011, I found myself single and intrigued by the dating world. As part of my undergraduate studies at UC Berkeley, I embarked on a 100-date experiment.

I spent a year going on dates with over 50 men.

One key strategy I used during this experiment was MegaDating.

MegaDating is the process of dating several people at the same time to diffuse your energy and increase your confidence. It’s a strategy that helped me find a happy, committed relationship, and it can work for you too!

If you want to learn more, head over to my calendar and book a 1-on-1 Zoom session with me today!

During our intro session, we’ll discuss your dating roadblocks, your goals, and we’ll determine if my program, Dating Decoded is right for you.

I look forward to talking to you!