12 First Date Conversation Starters That Will Reveal If They’re a Personality Fit
First dates can be exciting and fun, but they can also feel awkward if you aren’t sure what you’re looking for or how to break the ice. Since personality types vary, each individual will have unique struggles, but commonalities also exist in the dating realm. The main one? Finding a potential connection that leads you to a second date.
To help you on your dating journey, here are some first date conversation starters (applicable to everyone) to help you suss out your compatibility while keeping your own personality type in mind.
Personality type can help you find common ground
First up, you may be asking, how do these conversation starters apply to personality and how do I tailor them to my needs? Well, when looking at compatibility through the lens of personality theory, you likely already know if you get along better with someone who is more introverted or extraverted or have a more challenging time communicating with Thinking types if you’re a Feeling type, or vice versa. Keep these things in the back of your mind on a first date, and use conversation starters to get a feel for someone’s personality type and how they might align with your core values and personality.
Whether you’re looking for a life partner or want to take things slow, the ultimate goal for a first date is to see if you “click” with someone and can move on to a second date.
Keep an open mind. Remember, sometimes opposites attract, so don’t judge others too quickly or rule someone out based on their perceived personality type. Do look for red flags and personality clashes, but don’t overthink things. Some personality types (INFJ here!) take time to open up to others.
1. Do you go out every weekend or stay in?
Asking someone what they like to do with their weekends will help reveal some of their personality without asking if they’re an Introvert or an Extravert. Because some people aren’t aware of the true definition of Introversion and Extraversion, asking about their social habits is a quicker way to see which category they may fall into. I’ve lost count of how often people assume “Introverted” means “loner.”
Bonus question: What does your calendar look like during a regular week?
2. What drew you to your career path?
A person’s career choice says a lot about them, but if you ask why they chose their job, even better. You may get a sense if someone is a Type A or B personality, for example, based on the type of work they do or how they feel about work. Someone who chooses a career based on parental expectations or doesn’t feel the need to do everything “perfectly” is likely a Type B personality.
Bonus question: What’s your dream job? Money is no object.
3. What’s your biggest passion?
Exploring a person’s passions is a great icebreaker. Not only does this question help you discover if you have shared interests, but it also points to what makes them tick. For instance, if they love the arts and creative endeavors, you may get an inkling they’re an Enneagram Type 4 or one of the more creative 16-types like INFP, ISFP, or INFJ. Conversely, someone with more kinesthetic or intellectual hobbies may have a different personality type than you if these are not your strong points.
Bonus question: Do you have a niche interest you don’t often tell people about?
4. What drives you to get up in the morning?
This question is a great way to ask about someone’s values without being explicit. It can come off as lighthearted (albeit serious) and give much insight into a person's identity. An INFJ, like myself, might answer they’re driven by the desire to make a difference in people’s lives.
Asking this question is a less threatening way to skip the small talk and get into deep conversations.
Bonus question: Describe your perfect day.
5. Describe an experience that changed your perspective.
It’s nice to know your date is exploring personal growth. Asking about a perspective-altering experience will get you into their mindset and where they might be in life. But also, this is an excellent opportunity for storytelling on both sides. Knowing their perspective on things can lead to a good (or bad) impression to take note of.
Bonus question: Name a book (self-help book or otherwise), TV show, movie or album that changed your perspective.
6. What’s the first thing you would buy if you won the lottery?
For humanitarian types and real people-people, this is a good question to see if someone is caring enough to mention some sort of charity. However, this is also a question that can set your imagination wild. Priorities matter to every personality type, and if theirs appear to align with yours, you’re off to a good start.
For added fun ask: What’s the most frivolous thing you’d buy if you had an endless budget?
7. Who are three famous people (dead or alive) you’d like to have dinner with and why?
In line with the idea that you’re like the company you keep, who someone chooses to spend time with in an imaginary scenario can reveal a lot about their interests, values and mindset. You may find their answers surprising. For example, someone who doesn’t seem intellectual by their first impression (because they’re reserved or closed off) may suddenly riff on why they’d want to meet Einstein to discuss his theory of relativity.
Or you might just discover you both love Beyoncé.
Bonus question: Who was your hero growing up?
8. What’s something at the top of your bucket list?
Talking goals is serious business, but your date has their pick of anything on their list, from deep to outrageous. This question can elicit some quirky answers, so be prepared for anything. This is a good personality test to peek at their life goals, but it doesn’t have to be earth-shattering, so this might be a good test to see if your date shares your brand of humor.
Follow-up question: Are you a planner or more spontaneous?
9. Do you have a small friend group or a large one?
This question may get your date talking about their friends, and this is another helpful tip-off for their Introversion versus Extraversion scale.
Bonus question: What’s a typical night out with your friends like?
10. Where do you see yourself in five years?
The dreaded moment: asking someone to look five (or, gasp, 10) years into the future. This one might be scary, but it’s worth the discomfort to help you figure out if you’re in a similar mindset. Whatever your personality type is, you know if you feel like settling down soon or not (and to what degree that is for you). Their answer may also point to how future-focused, ambitious, driven, organized and “big picture” someone is — if they say they don’t like to plan too far ahead, you likely have got a live-in-the-moment type on your hands.
Bonus question: If things get uncomfortable, lighten it up by asking if they have any pets.
11. What’s your greatest talent?
Someone may answer this based on how they see themselves, not how others see them, so if your date seems less sure of themselves take this with a grain of salt. They’re probably more talented than they’re giving off (yes, I’m looking at you, perfectionistic Introverts). Either way, this question brings forth your date’s sense of worth. What do they value themselves for? Do they seem humble or too confident? Does their answer make you smile or feel like a red flag?
Bonus question: What’s a talent you don’t have but wish you did?
12. What’s a worthwhile splurge to you?
Asking someone what they feel justified spending their hard-earned cash on can be telling. Do they talk about self-care? The simple pleasures in life? If they mention buying gifts for others (not themselves), it’s a hint you might be on a date with an ISFJ, ESFJ, Enneagram Type 2 or someone with a Financial Love Style. Their answer may speak to their practical or emotional side — all things that can help you determine if your personality type matches or might clash.
Follow-up question: On the topic of spending, are they any good causes you support?
The Takeaway
Plenty of first date conversation starters can lead you to a conclusion about whether your date is a good fit for you, and the above list is nowhere near exhaustive. The easiest way to determine if you connect with someone is to compare a combination of your values, your personality type, your lifestyle and your short-term and long-term goals. Don’t be afraid to ask questions that make your date think — these tougher questions will open up deeper conversations, giving you a broader sense of who they are.
Only you know if someone is a fit, and sometimes it takes time. So try to keep your mind (and heart) open on first dates and have some fun. You never know what will happen!
