what questions to ask on a first date

What Questions To Ask On A First Date–Do You Like TV Dinners?

By Noell Romatowski


Let’s take a moment to say congrats to your first date with this new person of interest. You got through the 1st part which is finding which dating site you want to join. 2nd you decided on your online dating profile picture. You learned how to write a great online dating profile. Next big step is what questions to ask on a first date?

You already have some dialog via the dating site and hopefully have talked a few times on the phone. I am sure texting about where they grew up, family and about their hobbies.

The first date is so important for many reasons and it can be very nerve wrecking, especially for the more introverted personality. Take a deep breath and here you go!


Below are some great first date questions to ask and learn more about your date. These will help you to be more engaged and have fun at the same time. Leaving the date with more information and if you want to ask or be asked out on a 2nd date is the goal.

What do you want to be remembered for?

If you were to look back on your life, what do you want people to remember you most for. In asking this question you get to see more of their goals and what someone wants to represent in their life. Whether they want to be remembered for never missing a black Friday special at Macy’s, they had 5000 hours of vacation at work or that they fostered animals for 20 years and enjoyed helping animals find a good home you can get a gauge for their aspirations in life.

What is the worst date you have ever been on?

Hopefully they don’t blurt out…this date! Your date can let their guard down a bit and share openly with you. It will help give insight into what to stay away from or find out more about their likes and dislikes too.

It’s a good relatable question for both parties as most have a good story to share. Would love to be a fly on the wall to hear some of those shares!

If you won the lottery, what would you do with the money?

I think this question can let people share a bit about their dreams and have some fun too. A person’s morals and values will be exposed in this question without having to point-blank ask that specific question.

If they want to spend all the money on lavish things for themselves boats, cars rolling like they are a baller and not share with loved ones or do anything charitable with the money, it will tell you a lot. It can also help the conversation topics if they state I would go to Australia and you want to go there too! What if they do win the lottery you could maybe go on trip to Australia, you never know!


If you could change one thing about your life, what would it be?

I think this question is important to see if a person is a move forward in life person or lives in past and has regrets. Gives you some information on dealing with past and where their life is in the present moment.

We wouldn’t be who we are if you didn’t go through the good and challenges in our lives. If someone tells you they would change their childhood, that could be a huge sign for many other things residing there as well.

What is your most embarrassing moment?

I wouldn’t start the date with this question. If it’s going well and you feel comfortable answering this question yourself I say go for it and ask it. This will show you their vulnerability and if they can laugh at themselves.

As I shared in my article, Online Dating Questions To Ask A Guy-What’s Your Favorite Movie? my most embarrassing moment. It can be fun and really show their personality come out. I have been on dates where this took the date to a different level of comfort and made both of us relax more too.

What is one of your biggest pet peeves in romantic relationship?

On the first date, we are trying to impress and don’t want to say anything wrong per say. You will get an authentic response and can help to see if you are aligned in some big ways. If they state their pet peeve is a partner who’s on their phone all the time or phubbing.

If you’re a person who has their hand print permanently ingrained around your phone and you sleep with it under your pillow, it’s safe to say that it probably won’t go well from that point forward. It can lead to resentment in the long run.

Being cheap would be a pet peeve for me. Being a thrifty person is cool, but being a cheapskate as in, someone who won’t turn the a/c on the car to save gas and it’s 100 degrees outside. NO. NO. NO.

I do feel people who are cheapskates can be cheap in other areas of their life such as time, caring and just darn right not fun people.

Do you enjoying working out?

If you are an active person, either run marathons or work out at the gym and/or a yogi, this is important to know on the first date. If someone’s idea is walking to their car to go work is being active that might not be a match for you.

It can be fun to work out together or even take a kickboxing or Pilates class together. The world of working out and being active you can explore and have fun together both indoors and outdoors.

Do you enjoy social media?

It seems everyone these days is on all or some of the social media platforms. I do think it can be geared in general the amount of use in certain generations, but it really does depend on the individual.

Let’s face it, most already have probably checked out the persons social media platforms as it does share A LOT about a person these days. For some, this can be a deal breaker.

If you haven’t even been on the date for 5 minutes and they want to take a snap chat of you together with several filters, post your cool cocktail on Facebook and post the dinner on Instagram, is that cool with you? How often do you post? If you are posting 50 times a day it will tell you what hobbies or time that person will spend with you as they will be more concerned about their likes on Facebook.


Who did you vote for?

An article in the Washington Post, Go A Head And Talk Politics On The First Date, by Lisa Bonos, states that having a hearty political conversation could increase your chances of getting a second date by 91%.

This is according to a new Match survey of 5000 Americans age range 18-70+. If you are passionate about certain subject, such as the environment, that can be something you both can talk about further.

What is on your bucket list?

I want to go skydiving, drive across country, visit 10 countries and swim the sharks to list some. Do you want to do any of those too or is this person way out there for you?

It can be cool discussion topics and have each share why you want to do it or maybe you are planning to do one of your bucket list items. I did have date ask me once what a bucket list was, so that can uncover a lot too!


A first date is a big deal and can be a lasting impression. There is no more hiding behind the computer or phone. Are you ready to show up and have your A+ game on?

What questions to ask on a first date? Do you have any good ones to add to the list?

Would love to hear from you noell@thedatingbliss.com


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About Noell Romatowski

8 thoughts on “What Questions To Ask On A First Date–Do You Like TV Dinners?

  1. Food! For me it is always food. Ask me about food, and you got yourself a date. Too sad I am married now though LOL..

  2. Hey Noell,
    Loved your article on what questions to ask on a first date. This isn’t something I haven’t thought about in a love time as I’ve been married for over 20 years. My brother on the other hand got divorced a few years ago and is about ready to get back on the dating scene. He’s told me he’s pretty clueless so I’ll send him your website through a link he can access to get some tips.
    I like a lot of these and they make a lot of sense. My favorite is the most embarrassing. I have a ready story that is by far and away my most embarrassing and it let’s my guard down a lot.
    One of the ones I was surprised about was the political one. That is such a hot topic I would think it might lead to fireworks and the end of a first date!
    Great article,
    Mat A.

    1. Noell Romatowski says:

      Thank you Mat for reaching out! Yes please send him to The Dating Bliss! It can be so overwhelming. Here is another great article for him DATING ADVICE FOR MEN–Just Men Talk which may put his mind at ease a bit and he for sure needs to get back out there!

      I love most embarrassing moment too as it’s important to laugh at ourselves and have fun. Wouldn’t you want to know someone’s political stance and who voted for? Could be a deal breaker for some and great conversation too! Maybe some fireworks too..LOL

  3. Phillip McMullen says:

    These are very good questions especially the who did you vote for question. This will tell you if you’re aligned on principals especially from the last presidential election. Any woman that voted for the current administration would have definitely been a deal breaker for me.

    1. Completely agree! You can learn and see how aligned you are with A LOT with this question. For sure a deal breaker for some. Good to know sooner than later:) Appreciate your feedback Phil!

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