Mom & Son Date Ideas for the Early, Middle, and Teen Years

When can we have another, mommy? It was so much fun!

That question has always brought music to my ears. To hear my sons get excited when they could spend time with me, just me! That’s what most moms desire.

Mothers frequently ask me what kind of dates and how often we went out. There isn’t a hard fast answer because I had to consider the age, maturity level, unique interest, and my availability. Some seasons we went out weekly. But then, there were times it was once every three months. The frequency isn’t as important as being intentional about making date times happen.

Before I begin let me tell you about me, I’m a mom of five very different grown children (three boys, two girls, two daughters-in-love) I have the advantage of not only being able to look back but of asking them what I did that made our relationship what it is today. In preparation for this article, I told the boys I was going to write to younger moms and asked each of them to tell me some of their favorite times with me so I could share them with you. You might be surprised by how much the little things mattered to them. It was interesting that they said they enjoyed having one-on-one time together. They said it gave them a chance to share honest thoughts with me. They viewed me a trusted friend.

Perhaps what I did along with what they said will be a springboard to help you in your desire to spend time with your son.

Do what interests him. This may seem like a no brainer. It is sort of, but only if you know what your son enjoys doing. I was always studying my children. I paid attention to the subtle hints they’d make when we were out and about. I listened when they talked about something one of their friends did that sounded fun. I jotted those ideas down so I wouldn’t forget about them.

Make it special. Before the date, take the time to get dressed for the occasion. Your son will know this isn’t just an errand. It’s something worth getting ready for. The little things make such a difference.

Surprise him. Have everything planned and then surprise him by telling him to get ready to go out. You can tell him what type of clothes to wear or what to pack and when you’re leaving. Let him wonder. These impromptu activities can be memorable for boys. It’s also easier to do because they don’t need as much time to get ready as girls typically require. At least that is how it is in my house.

Tell him in advance. A little-advanced notice builds excitement plus it gives him time to put it on his schedule. Anticipation is a big deal to many boys. They like having something fun to look forward to. Warning: they might drive you crazy asking you questions.

Enjoy time together. It can be easy to use this time alone to discuss problems, attitudes, or behavior issues. Don’t! Unless it is understood beforehand, avoid using this time for that. You want him to look forward to your dates, not think it’s a bait and switch.

Now you might be thinking, this all sound great, but what did we do besides dig in the dirt, go camping, and play good guy bad guy? I will break this down to seasons of life and some age appropriate ideas to help get you started.

First, try to avoid putting a “date” into your errands day. That isn’t a “date” it’s getting errands done with a break in the middle. They can tell you’re trying to multitask. If that is all you can do right now, then make sure you take a mental break and be fully present during that time. Don’t be planning what you still need to get done. It will defeat the purpose of having a date.

The early years:

These precious years are full of wonder and delight. It’s also a trust building time as he learns to trust you with his thoughts, hopes, and dreams. And moms, every secret needs to be tucked away in your heart. Don’t repeat them to others. He might not think about them when he is little, but he will learn that he can trust you.

These years don’t take much planning or money to create a memorable date.

Let him get up after the other kids fall asleep to have ice cream and talk or play his favorite game.

Take a monthly morning or evening stroll with just him.

Take an afternoon while the other children are resting to make his favorite cookie.

Play together without letting others interrupt. No phones or multitasking allowed.

Read together outside under the shade tree eating chips and drinking juice.

Ride bikes around the neighborhood and let the conversation freely flow.

Listen to their dreams over a bowl of popcorn or some other snack.

Play a game of knock-out together.

Make a tent in their room and watch their favorite show together. No texting and don’t post pictures of your activity on social media. Let it be between just you.

Middle years:

These are the most critical years of growing up. One day he wants to be a man, and another day he wants to play with childhood toys. Try not to make him feel self-conscience about going back and forth. Be intentional to focus on him during your dates. I mean really listen. He will tell you what is going on if you ask and then listen. An important point to note is that your son may struggle to make eye contact like he did when he was younger. During these years I found shifting to more physical, competitive type of activities helped my sons open up. It provided time to talk in a non-threatening way.

Exercise together.

Go bowling or fishing or snorkeling.

Run a 5K or something similar.

Take him to their favorite movie.

Play electronic games.

Show him how to make his favorite food.

Plan an afternoon hike through a state park.

Take a mission trip together.

Serve the homeless or senior citizens together.

Teach him how to slow dance or some other form of dance.

Camp in the back yard.

Play Frisbee or go body surfing together.

Play tennis or another sport designed for two people.

Teen years:

Planning dates with teens can be a little tricky. Some teens might not want to do things that appear childish or silly. My boys talk about this season of “dates” the most. Remember your son(s) are becoming young men.

Take a mission trip together.

Serve in your community. Food pantries, city events, and VBS are a few ideas that they’ll remember.

Plan a special gathering for his friends at your home. Then shop, clean, and prepare the food together.

Plan a canoe or kayak trip.

Have dinner without siblings or other distractions.

Take him to a sports game. Basketball, baseball, football, or soccer are usually good choices.

Take them to an all you can eat pancake breakfast restaurant.

Do a DIY project together for their room.

Wash and clean his car together.

Binge watch his favorite movie series.

Play darts or pool and have snacks.

Incorporate food into everything. Food is a big part of the teen years for boys. I knew if we were going to have a fun time I needed to include food. Sure enough, all of their memories involved food.

As you can see dates with your son can be anything that he enjoys doing. The important factor is learning more about him as you invest in your relationship. He will feel loved, and his willingness to be open will increase. This is all because you took the TIME to be fully present on your date. I think it’s important for you to know everything we did wasn’t always fun. We had many dates fail. Bad experiences, unmanaged expectations, or wrong time all led to some big flops. But the majority of the failures was because I wanted my son to do something he wasn’t interested in. The good news is we can look back a laugh at them.

The goal wasn’t to have a perfect date. The goal was to build closeness, foster trust, and make them feel valued. You don’t have many years to enjoy special dates. I urge you to make this happen by getting a few dates on the calendar.

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Remember there is something special about the mother/son relationship. Use these opportunities to make lasting memories. You only have a window of time before work, marriage, and life make it hard to have dates.


Father, I want to keep his heart for as long as I can because when it’s time for it go elsewhere I want to give it to You. Help me have the strength and energy to pursue deep relationship with my son all of our days. In Jesus’ Name, amen.


1 Peter 4:8 “Above all, keep loving one another earnestly, since love covers a multitude of sins.”

Philippians 2:3-4 “Do nothing from selfish ambition or conceit, but in humility count others more significant than yourselves. Let each of you look not only to his own interests, but also to the interests of others.”

Luke 6:31 “And as you wish that others would do to you, do so to them.”

Hebrews 10:24 “And let us consider how to stir up one another to love and good works…”

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