Top 20 questions to ask (and to not) a girl on a date

When it comes to building a meaningful relationship, conversation is the fibre of a strong foundation. It pleases both women and men to find an ideal match that can engage them, listen to them and maintain that engagement.

First dates are more often than not, awkward and nerve-racking experiences – but that’s what makes them so exciting and tantalising! The idea that this is an experience so lacking in certainty and routine means that it can only lead to adventure and discovery.

If we ask ourselves what the purpose of a first date is, most of us would answer that the goal is to get to know more about the other person. While this of course rings true, first dates are also a great way for us to get to know more about ourselves and, more specifically, how we communicate; do we speak too little or too often? Do we have a tendency to interrupt? Are we a good listener? No matter where this first date goes, there is a certainty that if you pace yourself and are observant, you’ll be sure to develop your conversational skills and this can only lead to great places and greater relationships – romantic or otherwise.

These observations are particularly important when it comes to men. In a post #MeToo era, men are encouraged to question how much they value a woman’s intellect and to reflect on how important it is that all genders get an equal say. All too often, many women come away from dates to find that they were interrupted or that they were judged for their appearances. Comments on physical appearance and sexuality are delightful when sprinkled into conversation with someone familiar – but a first date is rarely, if ever, the appropriate setting to focus solely on these factors.

Having a mental list of go-to questions is a great way to break the ice and even out the conversation. This applies to those who are nervous or self-conscious about coming across as dominant, demanding or overly-talkative as well as those who feel unprepared and unsure as to what to ask to fill the initial tension and silences.

The following, when asked, will help you to get a sense of a woman’s personality, creativity and spark. These interesting, funny and engaging questions are great ways to open the flow of conversation on a first date but there is no need to ask all of them. Ultimately, the goal is to make her feel comfortable to talk about herself and ask about you, not to quiz her.

“What is your favourite music genre?”

1. Does she like rock, soul, jazz or folk? Ask her how she first discovered the genre and what it is about the feel that strikes a chord with her, no pun intended!
2. “Who’s your favourite actor?”
   What type of movies do they like? Do they prefer to go to the cinema or watch movies at home?
3. “Do you enjoy going to exhibitions?”
   For city dwellers, this activity is far more accessible for those that live in towns or the country. Regardless, art is always a great topic to talk about so ask her what floats her artistic boat – maybe she prefers cartoons or animations?
4. “What is the best holiday destination you have ever been to?”
   This is a great question that can lead to a whole conversation on travelling from food, literature and language to museums, history and general culture – dive deep!
5. “What is your dream job?”
   Ask her what influenced this dream job and what her inspirations are or were.
6. “What is your favourite food?”
   This could be a favorite meal to order, favourite dish to cook or favourite snack. Ask questions about the culture of the dish and where they first ate it.
7. “What makes you feel romantic?”
   Ensure to ask her with intrigue and also an impersonal tone. You are not asking whether you make her feel romantic. Romantic notions could come from literature or location or her idea of romance could sprout from her favourite movie. The question is implicit rather than explicit as you are simply asking her about her feelings on romance in general.
8. “What’s your favourite way to relax?”
   Does she like to exercise or go to the spa or perhaps she’s pretty chill and relaxes with ice cream and a good movie or book. Showing an interest in her downtime is comforting as she knows you are not defining her solely by her job title or professional life.
9. “What is the last book you read?”
   If she doesn’t read, tell her it’s no biggie! Ask her if she is subscribed to any cool magazines, podcasts or YouTube videos.
10. “Do you have a hidden talent?”
    She could be a doctor who loves to cook or an accountant who kills at karaoke – whatever it is, show that you’re willing to see past what’s on paper.
11. “What is something you’re proud of?”
    Give her a chance to talk about her achievements and the confidence she gained from them without her feeling like she is showing off by bringing it up out of the blue. This question is quite abstract so you may want to define it clearer for her to understand your angle which is best kept broad. Give her examples and ask if she is proud of a family member or a creative side-project or her degree.
12. “Who are the special people in your life?”
    This is always a lovely question to ask especially if you can tell that she is uncomfortable talking about herself. It gives her a chance to talk about her mother or teacher and what she loves about them which will provide you with an insight as to what personality traits she admires and aspires to.
13. “Would you consider yourself more creative or more practical?”
    This is a great question in that it is both broad and specific. It can lead to conversations about careers, ideas or interests.
14. “If you won the lottery what would you invest in?”
    A classic desert island style question, this one is so fun but also provides insights into her personality. Where would she buy property and why – does she have an infatuation with Portugal for instance? Perhaps she would invest in a tutor to teach her how to design couture garments? Her answer will give many insights to her interests.
15. “What is your favourite type of cuisine?”
    Food unites us all. Her answer could also give insights to her heritage and upbringing or her experience with travelling.
16. “Do you like animals? If so, do you have any pets?”
    Pet owners adore their furry friends and jump at any chance given to show a picture or two. Ask about her dog or cat and the relationship she has with them. It will be sure to make her feel familiar and comfortable right away.
17. “Are you a morning person or a night owl?”
    A question that gives insights to the way she works and socialises. Perhaps she’s a party animal or someone who prefers to brunch and read. Maybe she’s both!
18. “If you could live anywhere in the world, where would you live?”
    This could relate to both location and country as well as interior design. What would their dream apartment be? Would they love a library, big kitchen or cinema in their dream home? Just have fun and exchange ideas!
19. “What was the last show you binge-watched?”
    We all love to sit back, relax and dig deep into a juicy drama or hilarious sitcom. Ask her about why it is her favorite show. Maybe the reasoning is artistic (she likes the costume design) or historical (she loves Vikings).
20. “Would you rather be able to speak every language in the world or play every musical instrument in the world?”
    A fun question that can lead to a conversation about music and/or culture.

As previously stated, there is no need to ask every single one of these questions, they’re just here to help get the groove going and to open up the flow. The ultimate goal is to ask broad and implicit questions which she can then specify in her answer if she desires. Questions that are overly familiar or too specific can give off the impression that you have made presumptions about her before getting to know her. Along these lines, here are some questions and general subject areas to avoid when first getting to know your match.

1. “Wow, how do you eat so much?”
   Some people eat more or less when they are nervous and there are many other more sensitive and often medical reasons as to why she may have a larger or smaller appetite that day. Avoid commenting on how much or little she orders and finishes as it may open up a sensitive topic far too soon.
2. “How much do you weigh?”
   General comments on her figure should be avoided on a first date – even if it’s a positive comment! This may sound bizarre, but you may compliment her on a feature you find beautiful but one she was teased for previously in her life which could bring up bad memories. This is by no means your fault but while you may see this as a beautiful trait it may make her feel insecure or self-conscious. Best to wait till later down the line to have these sensitive and intimate conversations.
3. “Why aren’t you drinking?”
   Similarly to commenting on how much food she eats, avoid commenting on the amount of alcohol consumed due to potential sensitive and medical reasons.
4. “How many relationships have you been in?”
   As we all know, relationships are complicated and each of us have our fair share of stories and even skeletons in the closet. A first date is not the ideal setting to bring up exes or previous romantic experiences in general. She is here to be with you and to get to know you so it is best to live in the moment.
5. “How are you still single?”
   Again, this may sound like a compliment ‘wow, you’re so beautiful and lovely, how are you still single?’ but this is likely to make her feel uncomfortable rather than validated. Remember, this is only the first date so there is no guarantee that this relationship could last forever which would leave her ‘still single’ again. A person’s relationship status is a sensitive and personal topic which isn’t the vibe we are going for on a first date.
6. “You’re not crazy, are you?”
   You too may have your fair share of skeletons in the closet and unpleasant past experiences when it comes to women. You may feel like this question is necessary in order to ‘veto’ whether or not your next potential match will make life difficult. But let’s be honest, even if they were ‘crazy’ would they admit it? Furthermore, the term ‘crazy’ doesn’t feel appropriate in a day and age where we understand and empathise with mental health issues even if the person suffering wasn’t the right match for us.
7. “Where do you see this relationship going?”
   Woah, woah, slow down there and take the pressure off the pedals! Just like you, she is nervous for this date and doesn’t know what questions to ask and answer and besides, the excitement is in the mystery and uncertainty. Enjoy it while it lasts.
8. “How much money do you make? Are you rich?”
   A person’s financial situation is a personal and sensitive topic. They may have grown up with wealth but are now struggling due to the pandemic or many other reasons. Vice versa, her childhood may have been riddled with financial anxiety and uncertainty. Best to avoid bringing up this awkward topic.
9. “Do you like how I look?”
   A strong and long term relationship is never skin deep. She may find you very attractive indeed but asking her about it firstly reduces the appearance of your modesty and confidence and secondly may make her nervous to answer. She isn’t here for a ‘fling’ she is here to get to know your personality and interests.
10. “Do you get along with your parents?”
    Of course, for many of us, parents are one of the most important parts of our lives but for a woman who has a complicated relationship with a parent or perhaps doesn’t have any parents at all this question could bring up bad memories. This topic is best to leave it to her to bring up when and if she prefers.
11. “What are you?”
    Although you may mean no harm in asking this question, wording a question about ethnicity as “what are you?” can feel very dehumanising. The answer to the question is we are all human. If you are intrigued by her ethnicity, ask with sensitivity and intrigue. “What is your cultural heritage or upbringing” is a much better way to ask. Also please do not refer to her as “exotic” – she is not a fruit and this feels objectifying. Women of colour and white-passing women also want to be complimented for their individualism. For this reason please also avoid cultural stereotypes even if used as a compliment. Telling a shy, book-reading Latina “all Latin women are fiery, aren’t they?” will make her feel like you don’t understand her culture and that she can’t fit into the box you and society have built for her.
12. “You look/talk/dress just like my ex!”
    Comparing her looks or personality to people you have dated before is a bad idea for a first date. A first date is a fresh start and a clean slate which allows both you and her to arrive with all your uniqueness and individuality. Comparing her to others will kill her confidence in this realm so appreciate and focus only on the girl sitting in front of you right here and now.

Remember, if you ‘mess up’, ask the wrong question or if she demonstrates that what you have asked makes her uncomfortable in any way, simply apologise with sincerity and move on. If you are both kind and sympathetic people, you’ll both have the maturity to move on from the awkwardness, apologise and accept the other person’s apology. The conversation should be a 50/50 exchange so sit back, ask, listen, exchange and enjoy the presence of this new and exciting person.