Spread some happy

Getting time alone with any of my kids is so special. We are lucky to be able to spend most of our waking hours together as a family. But developing those one on one relationships is so important. And my mom and son date nights are about making memories. I am very pumped to share these date night ideas with you.

I put a lot of work into each one of my kids dates. It might seem silly but I want them to each be special because you never know which one will be the one they remember. And I’ll remember all of them. Plus I feel that I’m teaching them about making someone feel special. I hope they use the creativity and effort I put into our time to make the loved ones in the their life feel special too.

My husband and I decided we would each take one of the boys out once per month. Then we switch the boys on the next month. Our daughter is only two so she’s not in the date rotation yet. But let me tell you, when she has her first Daddy and daughter date I might explode with excitement. I’m going to dress her up in a little dress and he can pick her up at the front door and I’ll take a billion pictures.

But Back to the topic at hand.

I’ve discovered that having a good date with a kid is similar to having a good date with an adult. The most important thing that makes it special is the conversations. So I made a little cheat sheet list of conversation starters you can find at the end. I know it sounds weird to have conversation starters for your own child, but sometimes its hard to think of questions that are really going to open them up and get them talking about things you don’t know about them.

But lets be realistic about what they care about. To your child, they see the activity as the most exciting thing, so you have to have a good combo of both.


Usually the boys start making suggestions weeks in advance. I can’t undersell how big of a deal Date night is in our house. We have to plan the nights weeks in advance to work around everyone’s crazy busy schedules. So the planning starts early.

If there is somewhere really specific that the kids want to go, then its easy planning. Maybe a new movie just came out, so dinner and movie is a simple solution.

Sometimes they want something different and want me to plan it. In this case I will give them a few options and let them pick. And of course they always pick where we eat. Below are four creative date nights that I’ve done to make things really fun for the kids.

Here is my Super Awesome List of Mom and Son Date Ideas

The Arcade bait and switch

The arcade is great and kiddos love it. But let’s be honest, they burn through money fast. Its literally a child casino. So I am a big fan of making it a combo with a cheaper longer event. If you combine it with something like mini golf, it takes up a lot more time and is way less expensive.

I make a game of the first activity to make the Arcade the “Prize” at the end. If we go to mini golf, I will tell him that if he beats me, I will give him all my arcade money at the end. Then I pretend to do all sort of bonehead moves during the game to ensure a loss for me.

These are the steps that I map out the night with:

Step 1: Dinner

We went to a sushi restaurant because my son knows how much I love sushi and that Dad does not. So he thought maybe if he liked it, it could lead to sushi dates.

He’s so sweet and good hearted. He tried to power through, but this was the photo I took during miso soup and his face didn’t change much through the meal.

Guess I’m still on my own for sushi nights ha ha

Step 2: While Eating Suggest that you “make it interesting” Let’s say you were going to spend $40 at the arcade. Tell your kiddo that you were going to get $20 each. Even though you were always only going to spend it on them. Tell them if they are willing to challenge you and win, they will get your half.  

Step 3: Flub your way through golf or bowling to ensure that they win. Or you could even make up something like going to the river or lake and collecting and skipping rocks as a challenge. Anything creative. They will think its hilarious when you drop things, fall down or try really hard and can’t quite get it.

Step 4: Head to the arcade and enjoy some time playing the games!

Why I love it so much

The arcade is great and the kids love it but I have two issues. The fun is expensive and goes quickly! As well, the kids are focused on the games and the conversation isn’t a priority. By doing the golf or bowling first, you get a bit of quality time where you really enjoy each others company.

Print off the sheet for easy reference! Arcade Bait and Switch PDF

Mystery night

This one takes a bit of planning. But its strategic. I make the whole thing look like a giant mystery with envelopes and decisions made by the kiddo, but really the whole night is already planned and they just think its a fun adventure.

You definitely have to keep up the illusion that the night could go anyway depending on how they pick. Don’t let them see the extra envelopes. Shred them or hide them immediately after they pick.

Step 1: Line up 6 envelopes. Tell them to pick one to decide what activity you are going to do. In reality they all have the same answer. Destroy the evidence of the remaining envelopes so they never know. Then go enjoy that activity.

Step 2: Give them a second set of envelopes for them to choose where you are going to eat. You don’t have to do six. Maybe even just two or three. But have the restaurant pre-determined.

Step 3: In the restaurant, try to distract your little one so you can slip the server another set of envelopes. They will be so amazed when she presents them instead of you. Again they can all have the same thing written in them. It can be something like, getting dessert at a special ice cream shop. Or going to the bookstore to pick out a new book.

Step 4: When you get back in the car and they think the night is over. Give them one last set of envelopes. In that set, have one more bonus activity. Depending on the age of the child, it might be something like they get to stay up late and watch a movie when they get home, or take them to a late night movie

Why I love it so much

The whole night gives the illusion of being a giant game that they are playing and controlling. In actuality, you’ve planned it all. But to them it was an exciting night of possibility and chance!

This one takes some planning in advance and you have to pull it of on the night of, but it is so much fun! I think this might be my favorite mom and son date night. Print off the instructions for easy reference. Mystery Night PDF

Try Something New

I feel like all of us tend to get into a bit of a rut sometime. Same restaurants, same activities, same routine at home. Its nice every once in awhile to mix things up and do something you have never tried before. Especially when you can do it with the kids. Its so exciting for them and a fantastic learning experience.

There is always something new and exciting that can be fun to try together. I do a ton of research beforehand and then the week before I will give them about 5 options to choose from just in case I need to book something.

Some examples would be:

  • Indoor skydiving
  • An escape room
  • Renting a paddle boat
  • A hike they have never been on
  • Renting a tandem bike
  • Renting a paddle board
  • Cross country skiing
  • a parent and child cooking class
  • paint night

Then wrap the date up with their favorite restaurant or cook their favorite dinner at home

Why I love it so much

Encouraging kids to try new things is a valuable skill. It create adventure and exploratory behavior. Plus it create a new special and unique memory that’s shared between the two of you.

Its not very hard to plan either. Just need a little time a few weeks out. Print it off to remember Try Something New PDF

Play and Stay

This is a great combination of getting out to do something active, and then continuing your special time by having a sleepover and takeout when you get home.

This one is especially great for older kids who don’t always get to watch age appropriate movies because they have to watch more family friendly ones for their younger siblings.

Step 1: Set up a space somewhere that you can have a sleepover before you go out. When we did this last time, I set it up in the basement and had my husband take the kids for a drive when we were coming home so we could sneak in unnoticed. That way no one gets jealous and the child on the date still feels like its their time.

Step 2: Pick an activity that is really physical and will tire them out. Something like swimming, going for a long bike ride, go to a trampoline park or a climbing center.

Step 3: Ask them to pick their favorite take-out that you can pick up on the way home. Order the take out and then go to the grocery store to pick out movie snacks.

Step 4: In advance, I like to get them a little memento like a small stuffy or a fun pillow case that’s special from their sleepover. That way they can keep it and remember their fun night. Curl up together, pick a movie and enjoy the cuddles!

Why I love it so much

Have you ever heard the saying, couples that play together stay together? Relationships are strengthened through shared activities. Playing with your kids is no different. And then you get a whole evening of cuddles for the sleepover.

Print it off for easy reference. Play and Stay PDF

Fun Ideas for Conversation Starters

I made this list to try and come up with some little ideas to get the conversations going. I find I’m guilty of talking at my kids most of the time. Did you do this? Don’t forget to finish this. Come eat. Hurry we have to go! These are all regular sentences out of my mouth. I’m sure out of all of our mouths

When it comes time to sit down one on one and have a real conversation, sometimes I get a little stuck on what to ask. And more importantly, I Want to teach them to be good conversationalists with creative and thought provoking dialogue. I think, as most things, its a great teaching opportunity.

To balance it out, I came up with 10 funny and silly questions. 10 more emotional or soft questions. And 10 thought provoking questions.

Fun Questions

  1. What language would you like to learn?
  2. What are the top three things you want to do on summer vacation?
  3. If you owned a restaurant what would it look like and what kind of food would it have?
  4. If you could create a new holiday, what and when would it be?
  5. If you could try eating anything in the world, what would it be?
  6. If we let you make all the family rules in the house, what would they be?
  7. Would you rather live in the downtown area of a city, on a farm or on a beach?
  8. If you could choose between invisbility, flying and controlling time, which one would you pick to be your super power
  9. If you could be invisible for just one day, what kind of things would you like to do?
  10. If I could grant you three wishes right now, what would they be?

Sensitive Questions

  1. What does it feel like when I hug you?
  2. What is your favorite memory?
  3. What do you think makes a person smart?
  4. You have a really cool friends. What do you think makes them so awesome?
  5. What’s something about you that you think I don’t know but want me to?
  6. What is your favorite thing about your brother and sister?
  7. What is the thing you like most about yourself?
  8. What are three things you think a friend should be?
  9. What makes you a good friend?
  10. What is your favorite dream? What do you day dream about?

Thought Provoking Questions

  1. You’re so good at helping others, what is your favorite way to help?
  2. If someone told you something you felt uncomfortable with and asked you not to tell anyone, how would you handle it?
  3. When you’re my age, what do you want your life to look like?
  4. What makes you happy? What makes for a happy home?
  5. What goal do you have for this year?
  6. Are there any questions that you’ve been too shy or embarrassed to ask before?
  7. Is there anything going on in the news that you don’t understand or have questions about?
  8. Are there things at school that your friends talk about that you don’t understand but pretend to?
  9. Is there anything in the world that you want to change? Why?
  10. If you could meet anyone in the world, who would it be any why? What would you do?

I love being able to make the time to have these special nights. And since we only do it once a month and then switch for the next month, I only get that evening with each specific son once every two months! I want to make every moment count for both of us. I would love to hear about any of your mother and son or daughter date nights in the comments below. Thank you for reading and happy Date nights!