First dates can be nerve-wracking territory. There’s the pressure to be charming, witty, polite and attractive, plus you’re trying not to succumb to first-date Tourette’s and say something that will blow your chances. At the same time, dating is a two-way street: 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 an interrogator. To ensure that you find out as much key information as possible while fostering a closeness and still holding up your end of an engaging conversation, here are the nine 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 Tinder matches. 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 good 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 Travelled?
Most people light up when they’re given the chance to discuss their favourite 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 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 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:
9. 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? Of course, depending on what you’re both looking for and how much chemistry has been sizzling between you, a more fitting final question might be, “Your place or mine?”
