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Blow Their Socks Off First Date Questions!

First dates can be nerve-wracking territory. You’re feeling the pressure to be charming, witty, polite and attractive, plus you’re trying not to say anything that will blow your chance of ever seeing this girl again. At the same time, dating is about you, too: It’s an opportunity to find out if you want to pursue things further, so you have to treat it as a kind of intel-gathering exercise, but without coming across like a job interviewer.


There's a fine line between fizzing chemistry and tumbleweed awkwardness on a first date. You’ve gone through all the usual first-date questions that are basically adult version of ASL (age? sex? location?) from university, but if you really want to make a connection then you need to be asking the right questions.


Relationship therapist Megan Bearce says if the goal of a first date is to see if there’s possibility there, a well-informed Q&A is the quickest way to form a bond. “Asking questions conveys that you have an interest in them and not just a date where all you do is talk about yourself,” she says. “You may find out that there are major differences you have on certain topics, and even if you’re physically attracted to them, knowing this early on can help figure out where it’s going.”


To ensure that you find out as much key information as possible while still holding up your end of an engaging conversation, here are some of THE best questions to ask your date:


1. What’s Your Dream Job?


Most dates — in fact, most first meetings — begin with the casual question, “So, what do you do?” This is a conventional but somewhat boring way to start a conversation: It forces your date to discuss her current job, whether she likes it or not, and it doesn't tell you anything about what she'd prefer to be doing with her time.

If you ask instead what work she’d most like to be doing or what her dream job is, you get an insight into her ambitions, values and priorities, plus you will instantly come off as more interesting and engaging than 99% of her other dates. If you're curious to know what she's currently doing for a job, in all likelihood that will flow naturally from this question, plus you have instantly broadened the scope of the conversation and guaranteed a more interesting, intimate chat.




2. What’s The Best Thing You’ve Read Lately?


This is a question which will reveal your date’s interests and give her a chance to discuss them for a while, which she's likely to enjoy. It's broad enough to encompass any books, blog posts and articles she's read recently, so unless your date doesn't read at all (a useful warning sign!), this should jump-start an interesting discussion.

Similarly, “What are you listening to lately?” can spark a conversation about music, radio shows and podcasts, and is more original and easy to answer than simply asking, “So, what kind of music are you into?” Delve for a while into the various art forms and elements of pop culture you both enjoy.


3. What Are You Looking For In The Dating World?


It's important to clarify early in the game whether you and your date have the same expectations. Is she looking for a husband, long-term relationship or simply a casual hook up? And are you happy to oblige? Be clear on what you're looking for in return, because if you have mismatching intentions it’s best to clear that up earlier rather than later, before feelings get hurt and communications misfire.


4. Do You Have Any Siblings?


This is a fairly generic question, but it's a useful, low-stakes entry point into a discussion about her family and upbringing, which is always a fruitful topic to explore on a date. A person’s family background can provide clues as to what they're like as a person and about your compatibility, so try to extend the conversation beyond a simple listing of siblings into a polite discussion about where she's from and how she was raised.


Resist the urge to play armchair psychologist or to get too intense, though — if her parents are divorced that doesn't mean that she's “damaged” or doomed to end up the same way, for example, and try not to pry about contentious personal details or dredge up painful memories. Aim to ease her in a sweet spot where she's comfortably discussing her family life but not feeling too vulnerable, because listening to your date talk about her background can give you a much fuller picture of who she is, and gives you the chance to provide her with the same.




5. How Long Have You Been Single?


Previous relationships can be fraught territory to bring up on a first date, but getting some idea about your date’s relationship history when you first meet is useful. Asking how long she's been single helps to determine whether she's a permanent bachelorette or serial monogamist (or something in between), and it does so in a non-invasive way. She can answer with a simple “six months”, say, but it allows her to elaborate if she'd like to. A good follow-up question is, “Was that your longest relationship?” if you want to spark a deeper discussion about her relationship history, and yours.


6. If You Could Have Dinner With Any Three People, Who Would You Choose?


Sure, this one won't win you many points for originality. But it's a classic ice-breaker for a reason: It allows you to instantly determine what kind of people your date finds interesting, and for what reason. The fact that it's a slightly clichéd questions means she may have already thought of an answer, which can help to avoid stilted conversation. If you're terrified of seeming unoriginal, tweak it slightly: Maybe ask which three people she’d want to be marooned with at sea, or who’d be in her ideal Power Rangers crew.


7. What’s The Best Place You’ve Ever Traveled?


Most people light up when they’re given the chance to discuss their favorite holiday or trip. It's light and evokes positive memories so it's perfect first date territory, and you’ll learn what kind of explorer she is: did she backpack through Southeast Asia for six months on the cheap? Did she splurge on hotels and shopping in New York? Did she study abroad in Copenhagen? Her answer will provide an insight into what she enjoys and how she conducts herself in unfamiliar locations, and if she hasn’t done much in the way of travel (or if you haven't), it naturally leads into a discussion about dream locations yet to be visited.




8. What's the one city you'd move to in an instant?


Is she the type of girl who’d want to move somewhere fast-paced or does she want peace and quiet, opting for farm life in the middle of nowhere? Her choice can reveal a lot about her likes and dislikes, but it also tells you where she’s at in this phase of her life. This first date question will allow you to find out if she would be daring enough to relocate to a new city without hesitation, or if stability is more of a priority.


9. What's it like being a .... (insert their profession here).


Sooner or later the conversation trickles onto the topic of jobs. People spend huge chunks of their time at work so they generally have much to say on the subject. Find out what she feels about her career. Is she only in it for the paycheck, or does she have a passion for it? This conversation doesn’t have to be boring, focusing on the office politics she has been wrestling with or all the so-called interesting stories about her bad boss. If it hits such a dead-end, the question can lead into talking about her ambitions, which is often much better ear fodder. You’ll gain some knowledge about where she’s headed in life and how she intends to get there. Lend a golden ear to show your interest and pay attention for yourself too. You have plans of your own to succeed at, so finding out hers can show just how compatible you are and if your paths are heading in similar directions.


10 .What was the best trip you’ve ever been on?


Chances are, everyone has been somewhere that meant a lot to them. Travel is a topic that connects people and it’s not too personal that it feels invasive. “This kind of question can help you determine how adventurous your date is, both as a traveler and in their life. Do they like the unknown? Do they like trying new things? This question will answer it,” Bearce says. Listen to how they describe their trip, too, she says: “You could learn they liked the fancy hotel, room service and shopping, where you’re more of an outdoors or camping person, which could be a clue that there are some differences.” If they mention, and can laugh about, mishaps during traveling – missed flights, language barriers, unexpected delays – it might signify they’re willing to tackle challenges head-on.




11. If you had the day off tomorrow, what would you do?


When you’re working 9-5 (or 7 or 8), it can be easy to get wrapped up in your never-ending to-do list instead of thinking about what you would do if you didn’t have to log in so many hours. It’s likely your date feels the same way and hardly even imagines what she would do if she didn’t have to go into work the next day. Founder of the Professional Wingman,


Thomas Edwards says that creativity in your questions can take your conversation from dull to awesome instantly. “Get specific but let them have the chance to elaborate and tell a story – that’s when you’ll really get to know them,” Edwards says. This question will reveal if they’d love to sleep in, have a long lunch or brunch, or if they’d do something spontaneous like take a day-trip to another city nearby. Whatever it is, it’ll give you a view into how they like to spend their downtime and if that’s something that matches with your taste, too. It also lets you spitball ideas for date number two.


12. I have another wedding next weekend – seems like everyone is getting married! Are all your friends getting hitched, too?


It might seem like a red flag to bring up marriage on a first date, but sex and relationship therapist Dr Kat Van Kirk says an indirect reference will help you detect her feelings toward her friends, family and future. “You can often make conclusions about what she wants out of life by discussing the people she is the closest to,” she says. “Asking a benign question about whether her family lives nearby can also be a great way to pick up on how she handles those relationships and if she has outstanding issues.” Pay special attention to how she describes her friends – is she catty and dismissive or doting on them? – because this is likely how she’ll discuss you in the future.




13. Do you have a pet?


Bearce says this question can lead to all sorts of conversations, including about her childhood and any experiences with animals. Look for opportunities to bring it up organically – like you’re walking by a dog on the street. “If you are an animal lover, this is great information and can also give you indirect insight into their personality,” Bearce says. Another vital piece of info you'll glean here is whether she's on the same side of the great Dogs vs Cats as you. (For reference, dogs win every time.)


14. What’s the most exciting thing you have coming up?


Edwards says by asking what’s ahead in their life and why it’s getting them amped up, you’ll see the things that matter to them. They could mention a big presentation, a fun trip, reuniting with a family member or doing something special for a friend. Whatever it is, the insight into their internal countdown will give you some clues on what this person is really like. It also gives you an opportunity to talk about the things that you have going on and why they’re special to you – seeing how she reacts to them will give you some idea of whether she'll be there with you.




15. What would you do right now if you had a million bucks?


You can ask her about her hobbies, or you could throw her this question and see how she catches it. What she would do if she landed in big money overnight is probably something she has let her imagination toy with before (as have most of us), so it will give you a glimpse into her interests and priorities, but also spontaneity levels. The benefit of this first date question is that it comes across as fun, thus putting her at ease while giving you some insight into what she’s all about.


16. What’s the scariest thing you’ve ever done?


Just how risky is this hot tamale? This subject not only makes for some interesting anecdotes, but it helps you gauge her adventurous side and what risk levels she is comfortable with. Look into the future: If you start dating and invite her to go bungee jumping or mountain climbing, will you be sharing that adrenaline or will she be sitting on the sidelines bored? Explore her sense of adventure and see if your fun thresholds are on the same page.


17. What Are Your Plans For The Weekend?


First-date questions don't all have to cover big, meaning-of-life topics, and this question is useful to establish what your date does for fun, without the social awkwardness of asking, “So, what do you do for fun?” This way you can learn about any weekly soccer games, wild partying habits or child custodial battles with a simple, off-the-cuff question. If your date is on a weekend day, just ask about the remaining, or previous, days.

Bonus: This question gives you some crucial intel for the next question, the final best thing to ask your date:





18. Do You Want To Go Out Again Next Week?


Let’s face it: the aim of the dating game is to find someone you want to see again. If the date's going well and all her answers have indicated compatibility and mutual interest, why not lock in a second date? 




Make The Right Impression


You’ve kept her intrigued with your interesting first date questions and are now in a better position to decide if this first encounter could possibly lead to a romantic sequel.  But talking is only half of it -- also take note of her body language as this reveals unsaid bits about her personality. It’s often the inside scoop on what she’s really thinking but doesn’t realize it’s displayed for you to see.
By the end of the night, with this approach, you’ll know if you’re going to invite her out again -- or if the only person you want to call is the waiter so you can settle the bill and make a speedy exit.






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