20 Great Questions to Ask on a Date

How to get great at face-to-face conversation in a text heavy world.

Here’s what I find interesting. Almost every one of my clients complain about the same thing. People don’t talk anymore. They text. Ladies want the guy to call them. Men want the women to answer the call. So let me get this straight. If both sexes are wanting calls and conversations why aren’t they having them? All I see as a dating and relationship expert are great people out there with bad communication habits rooted in laziness. It’s no wonder that when people finally meet face to face they wonder what the hell to talk about.

When you’re dating with purpose, it’s pivotal to get very clear on the kind of life you want regardless of whether or not you are rolling solo or in a relationship. This clarity, which I find many people get overwhelmed by, helps to determine the most suitable partner based on goals, ambitions and values.

Once clear on what you want, then it’s time to ask the right questions to determine if the person you’re dating is a match. You also get clear on how to talk about yourself, another thing I find my clients, typically Type A, success-minded professionals, struggle with. They often launch into interview mode. You’re bonding with another human not getting a job.

My take is that by the time people have reached 35, 40, 45, they have had enough life experiences and bad programming to make them second guess and overthink. They’re trying to think about who they need to be so that the other person likes them. It’s a desperate energy that messes with communication. It turns people off.

This combined with dating apps, social media and texting, we see an unfocused dating style where people waste time not knowing anything of substance about the other person.

To help, I decided to offer up some key questions that serve as conversation starters as opposed to an interview. They key is to know what you’re listening for. Do you?

20 Great Questions to Ask on a Date

1. Which 3 people influenced you the most in life and why?

Maybe it’s a parent, a sibling, a teacher, a character from a movie or book. Pay close attention to what they’re saying then be ready with your reply if asked the same question in return. Let’s say their 3 are their mom because she was a single mom who became a lawyer, their grandmother who cared for them while mom studied, and their 8th grade math teacher who said that girls can absolutely do math. Do you see how much you can learn about a person? How would you further the conversation?

2.  If I had lunch with your mom, your most significant ex, and your best friend, what would they say are your best qualities and what would they warn me about?

This is a badass question. It’s bold enough and if you’re asking, then that means you are prepared to answer. They may reveal they don’t have a best friend or that they don’t get along with their mom or they are incredibly close with their mom. Maybe their longest relationship was 6 months 6 years ago. What if their ex would say they are terrible with money or flirts too much or needs constant attention? So much is revealed with this question.

3. What do you like to do for fun?

We’re always so focused on work so when we’re asked what we like to do for fun our mental state is changed. We start thinking about fun and we equate anyone who asks this question, with fun. Pay attention if they are resistant in any way to this question. If you’re a fun-loving person who is up-beat and positive this question will quickly help you to size up the other person’s fun IQ. If they have children, that will usually come up when this question is asked.

4. Where did you grow up?

This is a great way to get someone talking about their childhood without coming at them like a therapist. Remember it’s a date. Keep things light and interesting. If they had a rough childhood you’ll know it based on the reply to this question. I once got a guy to reveal how tough his parents divorce was on him by asking him what kind of bike he rode as a kid. When people trust you they open up. They trust you when YOU open up too.

5. What’s your family like? Do they live close?

You can tell a lot about people by the way they speak about their family. A client once asked this and the girl said her parents were total disasters and she and her sister went to live with an aunt which radically changed her life for the better at age 14.

She went on to get a scholarship and eventually reconnected with her parents who she sees a few times per year.

My client, a self described recovering player now looking for a wife, was so captivated and inspired by her story that he knew he wanted to see her again.

6. Do you have any allergies?

This is an important question to ask if you have a pet. The last thing you want to do is get to like someone only to have them break out in hives when they meet your dog. Some people are allergic to certain foods, plants, medicines, you name it.

7.  What inspired you to do what you do for a living?

If they love what they do you’ve just gave them permission to talk about what they do. Make sure you listen. If they can’t stand their career and would love to make a major career move, they’ll reveal this too. People are working 9 hours per day. Work matters and this question will tell you where they are professionally which is important.

8. What would you do for free if money didn’t matter?

I love this question because it calls forth creative energy. It gives someone the permission to speak about their truest passions and how they would ideally love to make their mark in the world. A female client of mine asked this on what she thought was starting off ass yet another bad, boring, date.

This question was a game changer. She learned that the guy she was with was an engineer who plays 4 instruments and writes music. They spent the next half hour co-writing a funny song on the back of a napkin and talked about their favorite bands.

9. What really pissed you off recently and how did you deal with it?

We all have different ways of handling anger. When someone is given the space to reveal what pisses them off, you can get a clear picture of whether or not they fly off the handle or are happy go lucky or somewhere in between. You’ll also get a sense for what does piss them off and if they have a short fuse or are patient.

10. When was the last time you spent money on something you really regretted?

A client of mine who wanted to know if the woman was dating was responsible with money asked this question. He presumed she was a spoiled princess because she was hot and dressed in designer clothes.

She said she regretted buying her last property. She revealed she took advantage of a great deal but was partnered up with others on the deal who let things slip through the cracks. She spent the next year trying to sell it. This launched them into a conversation about real estate investing, their views and attitude about money, something that is very important to be on the same page about.

He was pleasantly surprised that she started as a real estate agent right after college and at 37 has a nice real estate portfolio affording her designer clothes herself.

11. Do you have any pets?

The pet thing is a major lifestyle question. Let’s say you have allergies or have 2 cats or a dog or just want to know if the person is responsible for a life other than their own, this question is non judgmental yet opens the door to conversation that could reveal some deal-breaking information. I have a dog. If I met a man who wasn’t open to being around my dog, we wouldn’t be able to date. Time saved!

12. What are the most valuable lessons you’ve learned in life so far?

I love this question because it goes deep. It shows that YOU are willing to go deep and want to learn and grow with someone. People who aren’t into anything serious may find conversation like this too heavy. People who are interested in a serious commitment will appreciate the question and will ask the same of you. Be prepared to share.

13.   What are your favorite foods?

This is a great way to learn of someone is vegan, carnivore, vegetarian and what their relationship with food is. Some people eat to nourish themselves others for enjoyment. This is also a great way to talk about new restaurants you are interested in trying which is a nice segue into planning the next date.

14.   Where have you traveled? What was your favorite?

This launches into the travel conversation. Some people are travel snobs and end up ruining dates because they get up on their perch looking down on someone who may haven’t traveled as much or at all. The key here is to determine openness and the will to travel. What if you open someone up to traveling? What if because of you they finally go to Italy and you have the best time together?

Now if they are negative about travel and you love it then obviously it’s not a match. Also pay attention to the kind of traveler they are. Are they into adventure or culture or relaxation, sight seeing, shopping and partying? Do they travel on the cheap or only roll 5 star? These are important things to get clear on early.

15.   How do you handle fear? What’s got you freaked out these days?

This question accomplishes two key things. First it sets the space for open honest sharing and vulnerability. If you have issues sharing this then explore why. Many people think they want a relationship yet are guarded. One client of mine told me he asked this question and the woman he was out with revealed that she’s freaked out about a mole she had biopsied. She revealed her mom passed away from skin cancer 4 years before and at 43, she was freaking out.

He shared that his dad passed from cancer 8 years ago and that he also had a scare himself a few months prior but then got into CBD, meditation and all sorts of natural supplements and turned around his health. This led to a whole other conversation and date humber 2.

16.   When are you at your best and most confident?

This question reveals so much. You never know where someone is going to go with it. It’s a uplifting question because everyone knows when they feel their best. If you want to charm people while simultaneously weed out anyone who is low vibe and negative, ask this question.

17.   What’s your favorite thing about the life you’re living right now?

Pay attention if they happily and positively list a few things or… immediately pivot to negativity and complaining. No one wants to date someone who is bummed out about their life that they automatically default to the negative. You really want to surround yourself with positive people with something to add to a relationship and not the miserable people who think their key out of misery is a relationship. They’ll drain you. Ask this question. Sit back and really listen.

18.   What were you like at 10? What about 20? How are you different now?

When people go back in time they either have very distinct memories or feel it was more of a blur. This is another way to see how a person evolved, what they were into and going through in life in the different decades of it.

19.   What did you learn from your last relationship?

If they launch into trash talking their ex, any kind of victim talk, consider it a red flag. You’re handing them an easy question. If they’re that emotionally charged by it, they may not have gotten the lesson.

20.   What does an optimal relationship look like to you?

This is such an important question because just saying you want a relationship isn’t enough. We all have different desires and growth tracks. Get clear on the nitty gritty. Everyone says they want someone to grow with but I suggest getting clearer if they seem evasive. Following up with hypothetical slice of life questions such as, “let’s say it’s a Sunday, we’re together a year, what time are we waking up and what are we doing? is a solid question to ask.

The key thing here is really look at your life. Get clear about what you want and know what questions to ask to determine if the people you’re dating are it.

About the writer: Lisa Concepcion is a Certified Professional Life Coach through the Institute of Professional Excellence in Coaching (iPEC) and specializes in helping Type-A go getters who struggle with their love lives. As a dating and relationship coach, Lisa helps people get to the root of what holds them back from the relationship they truly want, radically shifts old disempowering beliefs, reprograms and reboots the mindset to attract love. Lisa resides in South Beach Miami Florida and Coaches people worldwide via Skype, Zoom and Messenger.