46 Mom and Son Date Ideas: Fostering Connection Between You and Your Boy

We’re bumping over the railroad tracks, heading to his soccer game, when my almost 11-year-old recognizes the spot. I’m distracted, focused on getting to the right field on time, when he exclaims, “Mom, that’s where you took me on the train!” I look to my left and see the beautiful bridge, rusted just enough to be charming but not creepy, and am snapped back to that special moment. It was one of our favorite mom and son dates.

A TRIP DOWN MEMORY LANE 

Five years earlier, at this spot, we were sitting on bales of hay on the open-air car of this storybook train. The black engine, with its charming red painted trim, whistled our arrival at the bridge, as we clacked slowly through sunlit foliage. The trees waved their oranges and yellows at us, and my heart soaked in the wonder I saw on his face. The rhythm and hum of the train, the fresh air, the magical bridge, the golden leaves reaching for our shoulders—it was a moment we’re both transported back to this very minute. 

As I drive, he’s looking at the tracks and the bridge and back to me, waiting to see the recognition on my face. I feel it, too.

I didn’t know until that day, on the way to soccer, that our time on that train all those years ago would connect our hearts this way. When we began those dates, we didn’t know how those hours would tuck themselves into our hearts, laid and layered like stones in a foundation. Yet, five years after our mom and son train date, here was another connection, born from that open-air car and that clackety bridge.

HERE’S YOUR PERMISSION TO NOT BE PERFECT

Now, you need to know this: My family is not a shining example of doing this mom and son date thing perfectly. We don’t have everything figured out, basically ever. We have plenty of nights of, “Oh, wait, what are we eating?” And we have more days of pulling dirty clothes from hampers to complete the soccer uniform than I care to admit. We don’t always get along, and I still don’t understand why these boys eat ice cream in the bathroom or play outside in socks.

My family is proof that connection isn’t saved only for perfect moments in perfect families. Connection with our sons is not hinged on perfection. Rather, fostering connection lies in this simple formula: time + effort. That’s it. As you consider how to integrate regular one-on-one time with your son, please hold close these encouragements: 

1. There Isn’t One Right Way 

Schedule dates ahead of time, or don’t. Plan big outings or keep it simple. Whatever works for your family is what’s best. In our years, we’ve swung the full pendulum in our approach. For a season, we enjoyed rotating monthly dates, based on our boys’ interests and ages, keeping to a relatively set schedule. Now, we’re in a season where we watch for opportunities to seize last-minute moments, like a special hot chocolate and movie night when we discover only two of the five of us will be home that night. 

2. It Doesn’t Have to Be a ‘Big Thing’ 

Mom and son dates shouldn’t be a stress. If figuring this out feels big and overwhelming, think smaller. Think about one afternoon next month when you could grab a couple of hours with your son, and then think on what he might enjoy. For our family—as our boys spend more time at work and activities, or with friends—finding one-on-one time takes more intentionality than when they were little. But even simple, unexpected windows, like grabbing an iced coffee together, can minister to your son. 

3. It’s Never Too Late

No matter how old your son is, you haven’t missed it. Be intentional and watch for times that might be especially meaningful for your son. Is your son walking through a rough time? Has your family calendar been especially busy and a timeout over pancakes or milkshakes might help? Is there a circumstance that calls for celebrating or encouragement? Watch for the need and be open to the opportunity, even if it arises at midnight on a Thursday (and honestly, why are teens so chatty after our bedtimes?).

It needs to be said, there is a point at which you will no longer be allowed to call them dates. Because, in the words of my 14-year-old, “That’s just weird, Mom.” If your sons are at that stage, just know in your heart it’s a date, but in theirs, it’s free food, and that’s enough.

HOW TO PLAN YOUR DATES

Here are some guidelines to help you with planning:

1. Study Your Son For Ideas

What energizes your son? What are his current interests? Is he outdoorsy or is he into video games? Does he need to have a ball in his hand or would he spend hours building legos? These are all clues for the kind of date that would minister to his heart. Some considerations as you plan (and see below for some ideas to get you thinking):

• Ask him to teach you about something he’s interested in.
• Hop on Groupon or your favorite coupon app to see what experiences are available in your area. This is how we’ve found out about concerts and circuses and Lego events and Ninja Warrior tryouts that we might not normally know about.
• Google museums and sports complexes and activities in your area—you may land on some new things you’ve not known were close by. For example, in my city we have a sign museum. Yes, an entire museum for neon and vintage and retro signs.
• Invite your son to plan the day or evening with you. Ask him what ideas he has for outings, and what fun things he might have heard about from his friends.
• Consider a simple outing. Perhaps a day at the park with a blanket, a packed lunch, and board games, cards, or a soccer ball will facilitate more connection than a busier day together could offer.

2. Decide on a Rhythm That Works For Your Family

You get to define what your rhythm looks like. For some families, it might work well to set a schedule, for others it might work best to seize the moment. We’ve done both. For a short season, planning ahead and scheduling monthly dates worked well. On the first of the month, we picked the day, and as the week approached, we planned the date together. But now, because we have more activities and commitments, we look for ways to seize the moment instead. If I take one of my sons to a soccer game, I might surprise him afterwards by taking him for a special “order whatever you want” breakfast.

3. Capture the Moment.

When we started our mom and son dates, we didn’t have a lot of other commitments on our calendar. Each boy had a journal where he wrote down the memory of our date, either with our help or independently. But as they got older, and our outings became less scheduled, we just snapped a quick selfie. Remember: Going on dates with your son shouldn’t add stress! Do whatever works.

4. Always Include Food.

Always. Enough said.