Questions To Ask On A First Date

Ever been on a date that felt like a job interview, or sat twiddling your thumbs in awkward silence? Ben Pechey is here to help, talking you through some of the best questions to ask (and to avoid) on a first date

Dating is an unpredictable pursuit. First dates can be amazing, but they can also be nerve-wracking, boring, disappointing or downright unpleasant. Something that a lot of people worry about is keeping the conversation flowing when you’ve just met someone. In this case, knowing a few helpful questions to ask on a first date can make a huge difference to how confident you feel, which can in turn increase your chances of enjoying your date.

This is where we come in, offering you some first date advice all about questions and conversation starters. We sat down with Queer Dating Coach, Ariella Serur, who shared some incredible tips to help you get the most out of your first dates by asking the right questions, as well as knowing which questions to avoid!

Break The Ice

Picture the scene, your date picked a restaurant, or a bar, or a crazy golf and karaoke assault course, and they’re already here as you arrive. How do you get over the first hurdle of the date and greet them? Fist bump? Kiss on the cheek? Awkward wave? “I’m a physical person, so I would probably ask to hug” Serur advocates. Open questions fare better than something needing a yes or no answer (e.g. ‘How do you feel about a hug?’ as opposed to ‘Would you like a hug?’)

There is also a potential benefit to hugging.  A huge variety of studies have been conducted that show a hug lasting around ten seconds can ease depression, reduce stress, and increase libido. This is in large part due to the feel-good and bonding hormone Oxytocin produced by hugs, meaning a hug could be a great way to kick start your date. Hugs and touch are also great communicators of emotion, as this study found, even between strangers.

However, if you don’t feel like physical contact or your date doesn’t, that’s also totally great! Many people are even more attuned to their own comfort levels and boundaries around contact and proximity due to the pandemic. If you don’t hug at the beginning of the date, it doesn’t mean it is doomed. It means that one or both of you are already comfortable asserting boundaries, which is a great start to open, honest communication between yourself and your date. 

How To Avoid Job Interview Vibes

Have you ever had a date that felt like a job interview, fielding questions that put you on the spot? 

“A job interview tends to be one-sided. You are trying to let the other person find out all they need to know. There will be some questions that overlap, but the difference on a date is the follow-up questions,” Serur says. 

She suggests that you can start with fact-finding questions. How do you spend your days? Where did you grow up? Have any pets? These are simple openers, to build a picture of the person sitting before you. “These are not the meat of a first date” states Serur, “these questions are only important because they allow you to gather more information, so you can ask more detailed follow-up questions”.

Even better, try to ascertain your date’s emotional availability to talk about certain topics – asking a question like ‘do you enjoy what you do?’ rather than the classic ‘what do you do?’ will give you a good clue as to whether talking about work is something that would be enjoyable for your date or not. If they hate their job, maybe they won’t want to talk about it. Likewise talking about family or childhood can be emotionally loaded for some people, so asking a question like ‘did you enjoy where you grew up?’ can help guide you as to whether to dig deeper or to move on, and can potentially let the other person open up. Trade information: it’s just as important to share your own story as it is to discover theirs. 

Try to be conscious of how you are asking the questions. Closed questions produce yes/no responses, whereas open questions create conversations, allowing you to have a back and forth! Ask questions that allow people to share what they love and the things that have made them feel great – ‘what did you enjoy about…’, ‘what’s your ideal…’ and ‘what’s your favourite…’ are great question starters to have up your sleeve. Of course, you may accidentally hit on a topic that is a source of discomfort, or dislike. Keep an eye out for signs that you might want to change the subject! If your date is avoiding the question, or eye contact, and seems unsure of how to answer, you can park the topic and move on to something else. In these instances, it’s often a good idea to stop questioning someone for a minute and take on the talking yourself, so that they can have a moment to regain their composure without feeling observed. 

Have Your Expectations On The Table

We can all have different expectations about what we’re hoping to get out of a first date, and we might not have had the chance to discuss these fully before we meet. A first date can be a good moment to talk about what you’re looking for without the complexities of established attachment. Of course, this isn’t always the case – it may be that you’re on a first date with someone who was previously a friend, or who you already know from social or work circles. In either case, it’s good to let each other know where you’re coming from so you can understand if your aims are aligned. 

“I usually go on a first date having an understanding of what we’re looking for,” says Serur. “I want to know what we’re doing on a first date! You can relate it to a job interview in that way, as you want to know what the job actually is! [At the end of the day, when we date we] are looking to link up with folks that have a similar desire to us.” 

Serur also suggests that there doesn’t need to be too much emotion in these questions. This can be difficult, depending on your circumstances and your hopes for the date, as the stakes can feel quite high. This can be true for any kind of expectations, not just for those looking for a long term relationship. Perhaps it’s more important to you to explore something casual, or connect with someone who has similar or reciprocal kinks. Whatever your motivation for going on the date, it’s important to be honest both with yourself and with the other person to avoid potential confusion and hurt down the line.  

In most instances, if you’re aware of your current relationship desires (non-hierarchical polyamory, monogamy, non-monogamy, casual sex or whatever it may be) it’s a helpful thing to disclose to your date so that you can both have a more informed idea of how you’d like to progress. Having said this, Serur also notes that it’s okay to not know exactly what you are looking for, or for you or your date to change your mind. The important thing is aiming for honest, open communication where possible.

Talk About Things You Both Love

There can be a moment on any date where you run out of things to talk about. In these moments it can work to bring in things you have experience of, as it can lead to a conversation that you can both participate in. 

Serur has this advice: “Think about what you love doing, and then ask them a question about that. It is always easier to recall our own lives over information someone else has said to us. So talk about the things that you love! I love to read and I love to travel, so it’s an easy thing to ask – ‘are you a reader?’ or ‘Is there anything that you have read recently that you have loved?’.” 

Air your passions! If you have similar interests, you can bond over that and if you have wildly different interests, this can be an interesting opportunity to step outside of your bubble or social media echo chamber and learn something new. Don’t be afraid of friendly debate – you don’t have to agree with everything your date says! As long as the conversation is kept friendly and respectful, you can absolutely challenge their assertion that The Royal Tenenbaums is the best Wes Anderson film. 

Questions Not To Ask On A First Date

So we have explored some questions you might want to ask on a first date. It’s time to explore the questions definitely not to ask! 

Save Dating History For Another Day

The topics of dating and sexual partners need to be approached with care and insight. They’re not off the table completely, but it’s worth being aware that questions like ‘Have you met anyone else lately’ or ‘How is your dating luck’ may lead us to compare and contrast, which could unearth a whole host of insecurities on your date. 

Serur says that “I wouldn’t ask about dating history until later. We tend to subconsciously compare where might fit in this person’s roster upon meeting them. Instead of asking them if they have been dating, I would probably ask if they had started to see friends [post pandemic] or how has the pandemic shifted their life around, what are their days looking like.” 

Know thyself – if you know that hearing ‘actually I met this gorgeous person the other day’ might make you feel sad and anxious, or if you don’t want to get into disclosures around your own dating situation, don’t ask the question. If, on the other hand, you know that you’d enjoy that conversation, then approach the topic mindfully. Be aware that your date will have their own boundaries and comfort levels around this conversation too. Rather than starting with ‘so, how many people have you slept with?’ you can observe their comfort for the conversation with a line like ‘so, I really enjoy talking about sex and dating on dates. How do you feel about that?’ If your date isn’t happy or comfortable, you can respectfully park the topic and move on to something else you’re both open to discussing. 

Assumptions Are Never Helpful

Assuming things about people’s gender, sexuality and identifying features is always a huge no-no. “There is always a chance that something might be difficult for another person, just follow their lead,” Serur says. If someone volunteers information – and it’s something about their gender or their body or how they understand their sexuality – then there’s potential scope for you to respectfully enquire. ‘Thanks so much for sharing that, I really appreciate it. Is that something you’re open to talking about/would like to talk about more?’ 

Remember that some questions may not provide the answers you expected. Serur reminds us all that  “everyone’s experience is so different, and society is built on systems of oppression. If you have more  privilege [or comfort on a subject] it is always best to follow the other person’s lead.” This is good advice outside of dating too! Always be led by what the other person has brought up, be open-minded, and if you have less experience or knowledge that is something you can be open about too. Just remember that the other person is here to date, not educate – as are you! No one on the date should feel like they’re having to disclose anything personal or difficult if that isn’t right for them at that moment.

Stereotypical assumptions can be offensive, triggering and can cause multiple layers of trauma to resurface or cause additional trauma. Even with the greatest will in the world, mistakes can happen. This resource from Awaken Blog is a helpful guide on how to respond if you’ve misgendered someone, with advice generally being to apologise, correct yourself and move on. Don’t make a big fuss, and don’t try to explain your mistake. On the other hand, if you are in the position where you have been misgendered, it is not for us to suggest how you ought to respond. If you want to stay and continue the date, if you want to leave, if you want to discuss it or not, that is totally up to you. Your response and how you feel at that moment are valid. 

Could Coaching Help You?

Ariella Serur is a coach that offers help for those that are getting back into dating, looking to date in a new way, or who want to date more effectively. Offering courses like  ‘Date Better Bootcamp’, with video classes and coaching calls, Serur makes the dating landscape feel less elusive and elite, and instead more approachable and open. 

A coach like Serur will allow you to understand your own needs and desires, which in turn helps to jumpstart a fresh approach to dating in the modern world. To find out more, sign up for Ariella’s newsletter and follow her on Instagram

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