239 Date Night Questions For Parents
Prepare for a spontaneous night of questions that won’t involve talking about your kids all evening.
Date night. The most anticipated night of the week… month… or maybe the year.
If you go on a date, I want to hear about it. What did you do? Where did you go? Who planned the evening? What did you talk about?
Before kids, date night was easy. It’s comical looking back on life before the kids arrived and thinking about the weeks when life was too busy for a date. Too busy with what?
Now date nights need to be planned weeks in advance, and all that planning for a Saturday night out when a babysitter costs 35% of your grocery bill might not seem worth it… but it is. And if you don’t believe me, ask researchers Harry Benson, and Steve McKay.
In 2016 Harry and Steve released a report titled Date Nights’ Strengthen Marriages, in which they studied 9,969 couples with children. No matter how you look at the data, regular date nights dramatically increase the health of your relationship, leading to a much higher percentage of staying together in couples who participated in them.
“I think date nights are important because you can get too complacent in the home routine and take the other person for granted, so it’s important to take a step back and look at each other; get some perspective,” said one participant.
But here’s the problem. When you’ve been married, and you have kids, you live with your partner, you literally get ready with your partner before going out, and you’re handling the coordination of your children with babysitters or parents, date night can seem anticlimactic. Let’s be honest, does writing out emergency contacts and thermostat instructions set the mood for you?
Now you’re at the restaurant, waiting for your server to arrive. The two of you look at each other, give each other the nod, and then you ask the least sexy question you could ask on a date, “Did you refill the diaper drawer before we left?” Now you’re entire night is spent talking about the kids, not each other.
I love my kids. I love them so much that I would do anything for them, including dating their mom. But the biggest question is, how often do you go on dates?
A 2020 article on moms.com said The Average Parent Hasn’t Been On A ‘Romantic’ Date In 3 Years. That seems too long. Many experts preach weekly dates. Somewhere between once a week and every three years, I think there’s a sweet spot for everyone.
Finding that sweet spot is entirely up to you because once a week, in theory, sounds great, but I don’t like the pressure that 52 date nights in a year places on your average couple. That’s like saying we should only eat organic, grass-fed meats, and it’s like, sure, but do you see these prices? My wallet isn’t set up like that right now.
It shouldn’t matter where you go for date night. Michelin Starred restaurants, Applebees, Hotels, or behind a locked bedroom door. A successful date night between two adults responsible for the health and well-being of children should be based on intention, not price.
Date night at your favorite steakhouse with bad conversation is not nearly as fulfilling as a date night at your local dive bar, eating happy hour apps over belly roll laughs.
As a Recruiter, I’ve conducted thousands of interviews. The best conversations are the ones where I am prepared. In the event that I’m not prepared, good conversation can be challenging to come by because good conversation doesn’t happen because you want it to.
Date night can be the same way. If we’re not prepared and don’t know what to say, you can spend the entire evening talking about the same thing you talk about daily; your kids.
You don’t have to create an interview guide for each date. In fact, it would be weird if you did. Spontaneity is still necessary for a relationship, but let’s combine preparation with spontaneity and kick off a great date night.
I’ve listed 239 questions for you to use during your next date and instructions to help make your next date a night to remember! You won’t need them all in one night, but the goal is to ensure you can use these questions on multiple dates and find a new set of questions each time.
Enjoy!
1. Download the app Pretty Random — RNG or any random number generator.
2. Select 1 as the minimum and 239 as the max.
3. When you’re ready, press “randomize”
4. Select the question attached to the number from the questions listed below.
And make sure both of you answer the question. I’m talking about actually answering the question, giving it thought and intention, even if it takes you a minute to think of a response (no one-word answers!).
And enjoy the conversation!
239 Date Night Questions for Parents
What does adventure mean to you?
What’s the last thing you can remember doing that was only about having fun?
What vacations do you want to take in the next ten years?
What is your ideal solo vacation?
What is the most adventurous thing we’ve done together?
How does our sense of adventure differ?
How can we learn from each other’s different ideas for adventure?
How have you changed over the years?
What is the most fun thing you’ve done by yourself?
When do you prioritize fun in your daily life?
How have we each grown individually since we first started dating?
How have we grown as a couple since we first started dating?
How are we different people from when we first met?
In what ways have we not changed since we first met?
What people have been most influential in your growth?
What defining moments shaped your growth the most?
What growth in your life are you most proud of?
How have we helped each other in our growth? Held each other back
In what areas do you still want to grow more?
What lessons have you learned throughout our time together?
What moments fill you with pure joy?
When is the last time you felt completely and totally content?
What do we do together that is most joyful for you?
Where in your life do you wish you experienced more joy?
What used to give you joy that no longer does?
What used to give you joy that you wish you could bring back?
What is something coming up in your life that you’re excited about?
What do you look forward to the most in your day-to-day life?
What about our relationship excites you the most?
How do you like to express and celebrate your excitement?
What personal accomplishments are you most proud of?
How do you define success for yourself?
How has your definition of success changed since you were a kid?
When you look back on your life, what would make your life a success
When have you confused your own definition of success with the definition of others?
Do you feel you’ve achieved your potential?
Right now, what do you consider a successful day? A successful week?
How have we helped each other be more successful?
When have we held each other back or hindered each other’s success?
How can we be more supportive of each other’s success?
If you had to answer one trivia question to win $1 million, who would you call for help?
If you had to give a TED talk tomorrow, what topic would you talk about?
How have your fears held you back in life?
What fears did you/do you have about our relationship?
How can we help each other overcome our relationship fears?
How often do your fears influence what you really want to do or say?
What fears did you use to feel as a child?
As a kid, who did you turn to when feeling fearful?
What is the first thing you do when feeling afraid?
What is the silliest thing you’ve ever been afraid of?
What kind of relationship gives you the most meaning?
How much energy do you put into the relationships that are most important to you?
Who do you feel like you can be most authentic with?
What are your most important qualities in a friendship?
What people have drifted out of your life? What caused this distance?
What have you learned from previous romantic relationships?
What are your most essential qualities in a romantic relationship?
How have previous romantic relationships shaped your perspective on love?
How can we be better partners for each other? Where do we fall short?
What types of relationships do you feel are missing from your life?
What is something that happened in your childhood that still bothers you?
What hopes and dreams did you have as a child that you have given up on? Why?
What is something you considered to be a symbol of wealth when you were a kid?
What would 10-year-old you think of you today?
How did your upbringing shape your view of what you wanted for a healthy family? A relationship?
What lesson from childhood has stuck with you the most?
Who had the biggest influence on you as a child?
What communication patterns did you develop as a child? Are they effective or ineffective?
What did you not like about your childhood that you want to change for your adult life?
What did you feel most ashamed of as a child? How might this shame still be affecting you now?
What was your perspective on money growing up as a child?
How did your family handle their money?
What is your current mindset about money?
What are your hopes concerning money for the future?
What are your fears concerning money for the future?
What are other ways that we contribute to the relationship besides monetary ones?
If we inherited a large sum of money, what would your first purchase be?
How would our lives be different if we had more money? Less?
How similar are our mindsets about money? Where are their conflicts?
How have we handled our money thus far?
What does a committed relationship look like to you?
What do you need to feel trusted?
When was the last time you didn’t trust me, and what could I have done differently?
What events or actions solidified your perception of my commitment?
What can we do to prove to each other that we’re committed to each other and our relationship?
How would you spend $1 million in the next 24 hours?
When have you experienced a breach of trust?
How did your upbringing influence your ability to trust others?
Who in your life do you feel you can trust wholeheartedly?
Besides our relationship, what other things in your life are you committed to?
What are your favorite sexual experiences that you and I have shared
What pickup line would you use to on me right now?
What is the worst pickup line you’ve ever heard?
How comfortable are you talking about sex?
When have you felt most intimate in our relationship?
In an ideal world, what would our sex life look like?
How can we prioritize sex more in our relationship?
What challenges do we experience in our sex life?
What do you enjoy most about sex?
How can we better communicate and support each other regarding intimacy?
In what situations do you find yourself struggling to communicate with others?
What default communication styles did you develop as a child that you still hold onto?
Are your communication styles effective or ineffective?
When have we experienced major miscommunication?
How can we better prevent miscommunications?
What style of communication do you prefer?
Who in your life do you have the most trouble communicating with? What causes this challenge?
What do you wish we talked more about?
What do you think we do really well with when it comes to communicating?
How can you improve your communication?
What is your idea of the ideal family?
How many children did you want to have as a kid?
How has comparison affected your parenting?
What makes raising kids harder than it should be?
What are the most important values you want to teach your kids?
What traits or qualities are you afraid to pass onto your kids?
What traditions from your family do you want to preserve?
What habits from your family do you not want to repeat?
How important is family to you?
What do you need to maintain a healthy balance of family and self?
How do you define creativity?
When do you exercise creativity in life?
How do you employ “creative living” in your life?
How often do you challenge yourself to try something new?
How often do you let your imagination run?
What is the most creative thing you’ve done/created?
What creative things have we done together?
How important is creativity in your life?
How can we employ more creativity in our relationship?
What creative outlets would you want to try together?
What goals do you have for the next five years? Ten years?
What goals do you want to achieve before you die?
What goals have you given up on? What made you give them up?
What makes something worth pursuing in life?
What do you need from others when you’re striving for a goal?
How does a fear of failure affect you?
What dreams are most important to you?
What is your process when working toward a goal?
What goals do you have for your love life?
What goals do you have for your work?
If you could work for any organization or business, what would it be?
How do you think you would fare in an apocalypse?
If you could host a dinner party and invite anyone, who would you invite?
Outside of conventional pets, what animal would you choose as a pet?
If you could play any instrument, what would it be?
What is a favorite recent dream you’ve had?
If you had one hour to communicate with an animal, what would you say?
What fictional world would you want to travel to for a day?
If you could gift everyone in the world one quality, what would it be?
If you could have one superpower, what would it be?
When you think about our future, what do you envision?
How has your vision for our future changed?
What do you still want us to do together that we haven’t done before?
What show or movie do you feel you would be a great character in?
Who is a couple who you admire?
What goals do you have for our relationship?
What most excites you about our future together?
What most scares you about our future together?
How can we support each other with any fears we have about the future?
What makes our relationship strong that will help in the future?
What memory from our past makes you smile?
What have been the highlights of our relationship for you?
What has happened in our relationship that you didn’t expect?
What do you think we’ve done well to reach this point in our relationship?
What have been your favorite date nights?
How have we grown as individuals? How have we grown ss a couple?
What do you want to bring back from our past that we’ve gotten away from?
What have been the biggest obstacles we’ve overcome together?
When reflecting on our past, what themes or patterns do you notice?
What about our past makes you excited for our future?
What’s a mistake you’ve made in the past that, when you look back on, you wouldn’t change?
What habits do you wish you could break?
What habits do we do as a couple that work well for us?
What do we do as a couple that doesn’t serve us?
If you could try a new hobby, what would it be?
How have your habits changed over the years?
How do your habits reflect your values?
When have our habits contradicted each other or caused friction between us?
How can we better support each other with our habits?
How can we introduce more spontaneity into our lives?
What is the opposite version of you? Or us as a couple?
What room in your house most represents who you are as a person?
What is a pet peeve that you have?
What behavior do you do that is most likely a pet peeve to others?
What phrase or word do you overuse when you talk?
What is the most ridiculous thing you’ve ever purchased?
What did you do when you were younger that makes you cringe to think about?
How has your fashion sense changed over the years?
What were your most memorable moments in school?
When was the last time you belly-laughed? What made you laugh that hard?
What did you notice about me first?
Is physical attraction an important part of whether you pursue a romantic relationship with someone?
Do you usually have a type? How did I fit with this type?
When you tell other people about me, what do you say?
What would you want me to tell other people about you?
What are traits about me that are special to you?
When you see me, what is the first thought that generally comes to your mind?
Do you ever look at people of the opposite sex?
How would you react if my appearance changed considerably overnight, such as if I dyed my hair a new color?
How would you feel if my appearance changed over time, such as if I put on weight?
Is there anything sexual we have not tried that you would like to try?
Where and how do you like to be touched?
Are you satisfied with the physical aspects of our relationship?
What would make our sexual relationship better for you?
In a perfect world, how often would you like to have sex?
Do you have any sexual fantasies you think about often?
How can I keep our physical intimacy strong throughout the day outside the bedroom?
What turns you on and what turns you off in a partner?
What is your wildest fantasy you never discussed with me?
Which celebrity do I resemble the most?
Which celebrity do you think would make the worst romantic partner and why?
What is my most attractive feature?
How important is intimacy for you?
How do you feel about public displays of affection?
Do you believe in grand gestures of love?
What is your love language?
What is your favorite inside joke of ours?
What is your favorite activity to do with me?
What’s been your favorite surprise?
What do you prefer - a simple home-cooked meal or dinner at a fancy restaurant?
Would you prefer a public proposal or a private one?
If I wrote you a song, what genre would you want that song to be in?
What do you think after you receive a super romantic message from me?
What was your first thought after our first real date together?
What attracts you toward the opposite gender?
What would the name of your memoir be?
What is something you always wanted try with me?
What would you name your drink if you had to name it?
Are we physically and emotionally connected enough?
When do you feel closest to me?
What is one thing we must do more often?
Do you think terms like “power couple” and “couple goals” prevent people from living their best life?
What would you do if I radically transformed my appearance?
What is a song that reminds you of me?
Which Disney prince and princess are we? Which superheroes best represent us?
Would you prefer a quiet night in or a wild night out?
What are the top 5 bedroom rules you think every couple should have?
What is your all-time dream concert?
If you had to star in a movie, would you be in a comedy or drama?