Date Night Challenges

Date Idea #3 | TIME FOR ADVENTURE

Date Idea #4 | Sweet Sensation

Date Idea #5 | Fill Their Tank

Date Idea #9 | Blast From The Past

Date Idea #10 | Corn Maze + Coffee

Date Idea #11 | Thankful TOGETHER

Date Idea #12 | Holiday Lights Drive

Date Idea #1 | NEW IN TOWN

Play the tourist and pretend that you are new in town. You can explore a mountain town, try a tour downtown, or head to the zoo. Tired of all that holiday spending? Simply stroll around Main Street to and window shop!

As you explore, discuss the following questions:

What kind of year has this been for you? Tell me the story of your proudest moment.
How have you changed in the last year?
Have your goals in life changed recently?
What goals do you have just for yourself right now?
What is one way you would like to change?
What things are missing in your life?
How has your outlook on life changed in the past two years?

Bonus: Write down a goal for your marriage or family for this new year and display it somewhere you can both see on a regular basis. Maybe go one step further and share your goal with friends or family.

Date Idea #2 | Family Matters

Find a family-owned restaurant to have dinner at this month. This can be the taco shack down the street or an upscale steakhouse. You can go to your very favorite spot or try something new. But make sure that this month you choose a restaurant that is family-owned.

When you go to dinner, discuss the following questions:

How would you compare yourself as a mother/father to your own mother/father?
What legacy do you want our family to take from your family?
How have you changed as a daughter or son?
What relatives have you felt closest to and why?
What wishes do you have for our family?
What were the highlights and lowlights of your adolescence?
Who was your childhood hero or heroine and why?

Bonus :

Leave a note to the family that owns that restaurant and tell them one thing you appreciate about the business that they have built.

Date Idea #3 | TIME FOR ADVENTURE

Choose a date outside of your comfort zone. You can go on a challenging hike or snowshoe trip. You can try that new adventurous restaurant – maybe the one where you take off your shoes and sit on the floor? Maybe you play hookey and ski for the day. Whatever you do, try something new and challenging for both of you.

On your date (or on the way there / home), discuss the following questions:

Where would you like to travel?
What adventures would you like to have before you die?
What would you like to save up for?
If money and time were not a barrier, what hobby would you enjoy pursuing?
What do you find exciting in life right now?
What are your biggest worries about the future?

Bonus: Get out your calendars and put your next adventure on the calendar. It can be finally booking a weekend getaway together or just planning an out-of-the-ordinary meal for your family next week. But give yourselves a little something to look forward to.

Date Idea #4 | SWEET SENSATION

Try a dessert tasting tour. You can make three different homemade cookies, cook up a gourmet dessert bar you’ve always wanted to try, or hop over to three different restaurants.

As you are eating, discuss the following questions:

What is something I do that you appreciate?
I love it when you…
When we were dating, how did you know you wanted to marry me?
Describe a date you would enjoy going on with me.
What is a personality difference that you appreciate (how am I different from you and you appreciate that difference)?
What is one way I could love you or respect you better?

Bonus:
Before the date, each of you write a quick note to one another sharing something good you see in the other person. Read your notes over dessert.

Date Idea #5 | FILL THEIR TANK

One of the best ways to connect is to serve someone else – TOGETHER. Pick a project (big or small!) to serve someone together in a tangible way this month. You could write a note to a family member, serve in Kids Ministry together, sign up to bring treats to your Kids Valentines party, or serve at a food bank. It doesn’t have to be a huge project, but do something together.

After you serve, discuss the following questions:

What kinds of behaviors and interactions put fuel into your marriage love tank?
What kinds of interactions or situations withdraw from your marriage love tank?
After listening to each other’s answers how will you intentionally make deposits to fill up your spouse’s tank?

Bonus: Pray out loud for one another at the end of your conversation. We know it can be a bit awkward at first, but God loves when you lift one another up in prayer.

Date Idea #6 | LEARN TOGETHER

People who are amazing at what they do can inspire us! This month, learn from an expert together. You can take a cooking class, a golf lesson (indoors?!), or go to an art class. If you want to skip a big bill, watch a cooking show on YouTube and make a fancy dinner together following their directions. Find a way to learn something new together this month.

After (or during!) your date, discuss the following questions:

How do you feel about work or parenting right now?
If you could choose any other career or vocation other than what you do now, what would you choose and why?
What are you good at?
What is something new you want to learn how to do or is there something of interest you want to learn more about?
What is the best feedback you have received?

Bonus: Compliment your instructor! Tell them how you see their talent and what impact it has on others. If you are in-person you can share your feedback after your class/session or you can send in a written note. If you watch something online, find a way to comment or email the instructor your gratitude.

Date Idea #7 | Masterpiece

Go to an art studio, take a pottery class, or grab some paints and canvases at home. The goal isn’t perfection—it’s to have fun creating something together. Swap paintings halfway through or make something inspired by each other. Share your finished works and laugh at the results!

Discussion Questions:

Do you consider yourself a creative person? Why or why not
What’s something artistic you’d love to try but haven’t yet?
What’s a time in our relationship where we made something great together?
What’s one way we could bring more creativity into our everyday life?
If our relationship was a painting, what colors or images would represent us?
What’s a creative date we could plan for the future?

Date Idea #8 | Take a Hike

Activity:

Choose a scenic trail, park, or nature preserve, and spend time walking together without distractions. Leave your phones on silent (except maybe for pictures), and take in the beauty around you. Pause at a lookout point or sit by a lake and talk before heading back.

Discussion Questions:

What’s one place in nature that made you feel close to God?
If we could take a trip anywhere to explore the outdoors, where would it be?
How do you think time outside affects your mood and mindset?
What’s a challenge we’ve overcome together that made us stronger?
In what ways do you feel like we’re “on a journey” as a couple right now?
What’s something in our relationship you’d love to grow or strengthen?

Date Idea #9 | Blast From The Past

Activity:

Visit a spot that holds a special memory in your relationship—maybe where you first met, had your first date, or a place that means something to both of you. Reminisce about that time, talk about how things have changed, and dream about where you’re headed next.

Do you live in a new town? Find an activity that reminds you of an early memory in your relationship!

Discussion Questions:

What do you remember most about our first date?
How have we changed as a couple since then?
What’s something small I did in the past that made a big impact on you?
If we could relive one day from our relationship, what would it be and why?
What’s a milestone we haven’t reached yet that you’re excited for?
Where do you see us five years from now?

Date Idea #10 | Corn Maze + Coffee

Activity:

Find a local corn maze, pumpkin patch, or fall festival. Get lost together (on purpose), grab a cup of cider or coffee, and make a night out of exploring, laughing, and enjoying the change of season. Snap a few pictures along the way—bonus points if you get one with matching flannel.

Discussion Questions:

What’s one of your favorite fall memories from childhood?
Do you enjoy the “getting lost” part of adventures, or do you like to have a plan?
If we could create our own fall tradition, what would it be?
How do you typically handle seasons of change in life?
What’s something you’re excited for in this next season of our life together?
Is there anything you want us to be more intentional about before the end of the year?

Date Idea #11 | thankful Together

Activity:

Take a slow dinner together (home or out), but make it special: bring a notebook and spend the meal listing out things you’re thankful for—big and small. Focus not just on life in general but what you’re thankful for about each other. Read them out loud when you’re done.

Discussion Questions:

What’s one way you’ve seen God’s faithfulness this year?
What is one thing about me you’re especially thankful for right now?
How do you think gratitude could change the way we face challenges?
What’s something small we could start doing to stay more grateful every day?
Looking back on this year, what moments stand out the most to you?
What’s a new tradition or ritual we could create around gratitude as a couple?

Date Idea #12 | Holiday Lights Drive

Activity:

Bundle up, grab hot chocolate, and drive around looking at Christmas lights. Make a playlist of your favorite Christmas songs, find the best neighborhoods, and rate each house (extra points for ones that go all-out). If you want, end the night slow dancing to Christmas music in your living room.

Discussion Questions:

What’s your favorite Christmas memory growing up?
If you could create the perfect Christmas Day for us, what would it look like?
How has the meaning of Christmas changed for you as you’ve gotten older?
What’s one Christmas tradition you never want to give up—and one you’d love to start?
How can we make the holidays more about connection and less about busyness?
What’s one thing you’re hoping for or praying for in the year ahead?