99 First Date Conversation Starters To Succeed

Conversation is the bread and butter of a good date. Sure, attractiveness lays a big part of the foundation, but how do you assess someone and find out compatibility and chemistry without conversing? So for that, you need effective first date conversation starters. And guess what? I’m giving you 101 for FREE, because it’s your lucky day baby.

What are first date conversation starters?

I went on a date last week and he said “So, tell me about yourself”. I stared at him blankly and mumbled something about being creative. This is not the way you want a date to go.


Do you want me to feel on-the-spot and bored, because I’ve been asked that very same question 1000 times? No. First date conversation starters need to be specific and stimulate conversation. I actually told this guy that his question was too broad and demonstrated some of the starters below to spice things up a little. Yeah, I’m a bossy bitch, I know.

Why Do We Need First Date Conversation Starters?

We need them to reveal the passions and priorities of our dates, highlight their dreams and communication skills, assess compatibility and most importantly, be engaging.

Positive comments and conversation trigger the release of oxytocin in the brain, which makes us feel good and elevates out ability to communicate, collaborate and trust others. And we love being asked to talk positively about ourselves, because self-disclosure produces the same pleasure sensations in the brain as food or money. Yeah, science, bitch!

See, Jesse agrees…

How To Use First Date Conversation Starters (Part 1)

Use these first date conversation starters responsibly; they’re not ALL the very first question you could ask on the date. E.g. don’t just rush in there with “Do you have any regrets in life?” unless you want them to say their roommate is locked out and GTFO. Start off with more vanilla first date conversation starters about travel etc. Then work up to deeper ones.

To help you out, questions that can be used at the beginning of a date are coloured green. Deeper questions to work up to are red. Anything in-between is orange. See, I’ve made a whole goddam traffic light system of first date conversation starters for you…

So… here’s the mother of all lists: *Drum roll* I give you…

101 First Date Conversation Starters

  1. If tomorrow was a national holiday, what would you do?
  • Learn about priorities, interests and what they’d like to spend time doing.
  1. What do you look for in a friendship?
  • Learn about personality traits they find important.
  1. Where’s your favourite place that you’ve lived?
  • Find out if they like travelling and what makes them like a place.
  1. What are you most proud of in your life?
  • Find out what they think of as good qualities in themselves.
  1. What was the best part of your day today?
  • Learn what small things make them happy. Also learn how they deal with stress during the not-so-perfect parts of the day.
  1. If you could buy a plane ticket to anywhere, where would you choose?
  • Find out what kind of holidays they like and engage their imagination.
  1. If there was a zombie apocalypse and we all died tomorrow, what would you do today?
  • Learn about how they prioritize things and how imaginative they are.
  1. What is your spirit animal?
  • Find out what kind of personality traits they think they have and have a cute convo about animals and shit. 
  1. Do you think that you relate to your star sign?
  • Find out if they believe in horoscopes and about their personality traits.
  1. Who is your favourite Disney villain?
  • Better than asking who their favourite Princess is. Do they sympathise with people portrayed as villains and see that good and evil are not simply categorized?
  1. Who are three of the most important people in your life?
  • Learn why they value people.
  1. What are you watching on Netflix right now?
  • Find out whether they like Netflix and what kind of things they like watching.
  1. What is the worst thing someone could do on a date with you?
  • Find out what they hate on dates – so you don’t do the same.
  1. What is your biggest fear?
  • Find out what makes them feel afraid and be prepared to see a more vulnerable side to them with this first date conversation starter.
  1. How do you like to spend your day?
  • Find out what they prioritize and what daily things make them feel happy.
  1. Do you work best in the morning or the evening?
  • Find out about their routine and body clock.
  1. Do you keep in touch with people you no longer see regularly?
  • Learn how much they value relationships and loyalty.
  1. What did you want to be when you were a child?
  • This will make them think deeply about their life and remember good times, hopes and dreams etc. You can also learn about their childhood. 
  1. What is a skill you wish you had?
  • See what skills they already have and what they think would be important.
  1. What is your family like?
  • It’s important to see how functional/dysfunctional their family is and what the dynamics are.
  1. Are you close to your family?
  • See what kind of relations they have and how they interact with them.
  1. Do you think people have any misconceptions about you?
  • This is an opportunity for them to air any frustrations and prevent you from making the same mistake.
  1. What instrument do you wish you could play?
  • Find out what kind of music they like, whether they have a sense of rhythm, whether they already play something.
  1. Have you ever had a really awkward date?
  • This is a good chance to have a laugh and possibly flirt a bit.
  1. What has been the best year of your life so far?
  • This gives them a chance to tell you what kind of events are most memorable and positive to them. Reflecting on positive things will make them feel happy on the date.
  1. What has been the best part of this year?
  • See above – again, reflective.
  1. If you were given a lump sum of money to start a business, what kind of business would you start?
  • Learn how creative, intelligent and ambitious they are and possibly what kind of a leader they’d be.
  1. What does your dream home look like?
  • See what kind of an environment they’d like to live in.
  1. If you could pursue any career, what would you choose to do?
  • Find out about their talents and ambitions.
  1. What is your Myers Briggs type? (Find out what that is here)
  • See how compatible they are to you and how they solve problems.
  1. Are you an introvert or an extrovert?
  • Find out about how they deal with events and communicate.
  1. Do you think that money makes the world go round?
  • Find out what value they place on money and what they think of the wider world.
  1. When you make decisions, do you rely on feelings or logic?
  • See which they prioritize.
  1. Do you think that robots will take over the world?
  • Just a light-hearted way to see how imaginative they are.
  1. Do you get uncomfortable with untidiness?
  • Learn how organized and tidy they are and whether this may lead to incompatibility.
  1. Do you like to plan your actions in advance?
  • Find out how organized they are.
  1. If you could buy anything from a designer store, what would you choose?
  • Learn about their sense of style and if they have expensive taste.
  1. If you’re in a team-working task, what role do you take on?
  • Finding out how they work in a team will allow you to get an idea of your compatibility.
  1. What is your favourite drink?
  • Find out about their taste with this easy first date conversation starter and possibly order that drink to set a positive tone to the date.
  1. Do you like tattoos?
  • See if they’re artistic, a bit badass or have different views on tattoos.
  1. Have you ever read a book that changed the way you thought?
  • Find out if they enjoy reading and how they analyse things they read.
  1. What’s your favourite book?
  • Again, find out if they like reading and the genre they’re into.
  1. What’s your favourite film?
  • Films evoke deep emotions, so find out why they like certain films.
  1. What are you passionate about in life?
  • Learn about their passions, hobbies, interests.
  1. What is a great memory of your childhood?
  • Find out what events were memorable and set a positive tone by getting them to reflect on good times.
  1. Do you have any regrets in life?
  • Allow them to reflect on your life and check out their honesty and emotional depth.
  1. When something bad happens, who do you text first?
  • Find out about who is important to them.
  1. Would you choose to go on a crazy road-trip or a luxury resort?
  • Learn about their lifestyle and holiday preferences.
  1. What is your favourite thing to eat?
  • Find out what their taste is like and make them happy by remembering their favourite food.
  1. What is the craziest thing you’ve ever done?
  • Find out how much of an adventurer/thrill-seeker they are.
  1. Where did you last go on holiday?
  • Everyone loves talking about holidays and reflecting on good times.
  1. What qualities do you look for in people you date?
  • See if you’re compatible in what you look for.
  1. What is a saying that you try to live by in life?
  • Find out what motivates them and their morality.
  1. If your life could be summarised into one line, what would it say?
  • See how reflective they are and what they really prioritize and aspire to.
  1. What is your favourite time of the day?
  • Find out about their routine, body clock and when they’re happiest.
  1. What is your favourite animal?
  • A simple first date conversation starter to see how much they like animals.
  1. What is one thing that people take a long time to find out about you?
  • Find out about any hidden talents or interesting personality traits.
  1. Do you prefer bars or clubs?
  • See whether they like just chilling or going hard and partying.
  1. What is your favourite dessert?
  • Find out about their tastes while stimulating delicious memories.
  1. Are you a vegetarian?
  • An important thing to know. If they are, steer clear of that steak for the time being… 
  1. Where were you born?
  • Also an important thing to know. Find out about big family events, such as moving country.
  1. If you had three wishes in life, what would they be?
  • Find out dreams and priorities and pretend to be a genie.
  1. If you won the lottery, what would you do with the money?
  • Again, dreams, priorities and ambitions. See if they’re a giver as well.
  1. What is your Chinese zodiac sign?
  • Find out how seriously they take horoscopes and what they think of their personality traits.
  1. Do you have a thirst for adventure?
  • See if they’re a thrill-seeker.
  1. What would you cook on Masterchef?
  • See if they enjoy cooking and what things they like making. See how creative they would be. Also gives you a chance to talk about TV shows you like watching. 
  1. Do you find it difficult to talk about your feelings?
  • This first date conversation starter will show how emotionally mature or sensitive they are and if there have been any big events in their life that they’d rather not talk about.
  1. If you really like something on the menu, do you always order the same thing?
  • See how much they value ingrained habits.
  1. What is the best thing about your personality?
  • Give them a chance to brag and tell you why they’re great. It will make them happy and you can see what they value in themselves.

70. If Morpheus offered you the blue pill and the red pill, what would you do?

  • See how adventurous they are… and whether they’re into narcotics.
  1. When was the last time you had déjà vu?
  • Déjà vu gives everyone goosebumps, so relive that shiver.
  1. Wind, water, earth or fire?
  • Find out why they like their chosen element and what that says about their personality.
  1. Do you find it easier to gain knowledge through books or hands-on experience?
  • Find out how they learn new information best.
  1. If you could invite anyone in the world to a dinner party, who would you invite?
  • See what kind of people they respect and what qualities they admire.
  1. Do you have any celebrity crushes?
  • Find out what attracts them to someone.
  1. If you could be a character in any movie, who would you be?
  • Find out what kind of people they relate to in life.
  1. If a film was made about your life, who would play you?
  • Again, see who they think relates to them.
  1. How do you think the world will end?
  • Find out about their beliefs and imagination.
  1. Have you ever had an interesting experience with drugs?
  • Talking about trips is fun. See what lies in the depths of their brains.
  1. If you were stuck on a desert island, what 7 things would you take?
  • Paint and exotic picture an find out what is valuable to them.
  1. How romantic are you on a scale of 1-10, with 1 being not romantic at all?
  • See if they’re someone who wants to be showered with roses and kisses or given more space. Possible chance to flirt here.
  1. If you had a superpower, what would it be?
  • Find out about their dreams and imagination.
  1. If you could stop time, what would you do?
  • Find out if they’d make the world a better place, rob a bank or both.
  1. What is one thing you wish you did less?
  • See how they self-assess and how honest they are with this first date conversation starter.
  1. What is the worst pickup line you’ve heard?
  • Laugh and possibly flirt.
  1. What is the best advice you’ve been given?
  • See how much value they give to listening to others and see what advice made an impact on their decision-making.
  1. What is your favourite way to stay healthy?
  • A more subtle and positive way of learning about their health and fitness than “Do you workout?”
  1. If you could go back in time, what year would you travel to?
  • Find out about their imagination and what kind of lifestyle they’d ideally like.
  1. Do you like mountains or beaches?
  • Find out what kind of getaway they’d prefer.
  1. What is the scariest thing that’s ever happened to you?
  • Relating scary stories is thrilling. See what their fears are and if they’re prepared to be a bit vulnerable. 
  1. Do you like scary movies?
  • See how much of a scaredy-cat they are.
  1. Do you think aliens exist?
  • Find out about their beliefs, theories on life and imagination.
  1. What kind of friends did you have in secondary school/high school?
  • Make them laugh by remembering how awkward and funny that time of their life was and reflect on what kind of a person they were/are.
  1. What is the nicest thing someone’s ever done for you?
  • See how much they appreciate things other people do and what kind of gestures make them happy.
  1. If someone cheated on you, what would you do?
  • Find out about their maturity and communication skills.
  1. Do you believe in marriage?
  • You’re not popping the question yet… Just seeing how much they value monogamy/polygamy and tradition.
  1. What kind of things make you competitive?
  • Find out if they have a competitive streak and what sports/interests/ambitions bring it out. Also check if they’re a sore loser.
  1. What is your hidden talent?
  • Find out any interesting information/quirks from childhood up till now.
  1. Are you good at keeping secrets?
  • See how much they value loyalty and what they do in scenarios of conflicting morality.
  1. Do you prefer texting or speaking on the phone?
  • See what kind of communication they prefer.
  1. Do you believe in God?
  • Yup, I saved the best first date conversation starter till last. Interpret that as you will…

How To Use First Date Conversation Starters (Part 2)

OK, so now you have absolutely NO EXCUSE WHATSOEVER to ask anyone what their favourite colour is, because you can’t think of a damn thing else. You’re welcome ????

Remember not to just fire 101 questions at them non-stop; LISTEN. Discuss the answers and turn them into opportunities for a two-way CONVERSATION. Learn from the mistakes of Hiddleston and The Boring Artist, who refused to let me talk through their monologues of bullshit.

Also know that this isn’t just about you passing a ‘test’ of not being awkward. It’s also about assessing whether they’re compatible with you. You’ve got the power.

More Hacks For First Date Conversation Starters

Yep that’s right mofos, I got more.

  1. Emphasize similarity. If you mimic some verbal and non-verbal language, they’ll like you more. Why? Because we like people who are similar to us and therefore perceive them as more attractive. Read more about that here.
  2. Give honest compliments – because who doesn’t like flattery? Renown psychologist Robert Cialdini agrees.
  3. Ask for their advice – This gives you the basis of commitment and consistency. It’s also flattering to be considered an ‘expert’ on something.

Think you’ll forget all of this? Note the first date conversation starters down in your phone, take a screenshot, email this article to yourself – share it with your friend who has a date (cos sharing is caring duh). This way, everyone will have captivating, scintillating and exciting dates and the world will be a better fucking place.