Dating As a Single Parent – Part 7: Dating When Both People Have Children

Two Parents, Multiple Calendars – Dating When Both People Have Children

You’ve found a dating partner who also has children! What a relief! Finally someone who already understands that life runs on school calendars, custody schedules, extra curricular practices, and whatever unexpected thing the day brings. You don’t have to explain or justify why you have to be home in time to tuck in your little one who needs his special song and his back rubbed in a way that grandpa just can’t manage. They get it!

They understand why a date might need to be rescheduled because a child woke up sick or because the other parent’s schedule suddenly changed. They are far more likely to ask if you need anything from the store. Wipes. Crackers. Maybe children’s Tylenol if someone has a fever. They are not the person wrinkling their nose at toddler germs. They have lived in that world themselves and they are unafraid! What a hero!

There is absolute comfort in that shared understanding.

At the same time, dating when both people have children comes with its own challenge. The biggest one is simple: finding the time to see each other.

When Two Schedules Meet

Two adults with children are rarely operating on open calendars which is why intentional conversation matter early. It is critical that you both talk honestly about availability and expectations. Not in a heavy way, but in a clear one.

How often are you hoping to see each other?
Is once a week realistic?
Is every other week more manageable?
Is one Saturday a month the only consistent opening right now?

None of these answers are wrong. What matters is whether there can be compromise or if the answers themselves (blissfully!) match.

If one person can only offer a single evening a month and the other is hoping for more connection than that, it is worth acknowledging early. Sometimes that simply means the timing is not right.

This is where prayer and honesty go hand in hand.

Walking in Agreement

Scripture gives a simple picture of partnership:

“Can two walk together, unless they are agreed?”
(Amos 3:3)

Agreement does not mean identical lives or perfectly aligned schedules. It means shared intention in that both people are willing to work toward the same goal and understand the practical realities that come with it.

If both want to build something and are willing to navigate the obstacles together, that spirit of agreement carries a tremendous amount of weight.

If one person is constantly adjusting (driving further, rearranging babysitters, offering grace when the other cancels) while the other remains rigid, the imbalance eventually becomes clear and resentment and disappointment can set in.

Compassion and Unity

When two parents are dating, compassion has to lead the way. Not just toward each other, but toward the children who shape both of your lives.

Paul writes:

“Therefore, as God’s chosen people, holy and dearly loved, clothe yourselves with compassion, kindness, humility, gentleness and patience. Bear with each other and forgive one another… And over all these virtues put on love, which binds them all together in perfect unity.”
(Colossians 3:12–14)

These qualities matter even in the early stages of dating. Compassion shows up when plans change. Kindness shows up when someone arrives late because dance class runs overtime. Patience shows up when schedules take time to coordinate.

The possibility of a flourishing relationship thrives in that environment.

When Children Eventually Enter the Picture

As the relationship grows, there may come a time to consider low-pressure family outings. This may even be before the children are told titles of “dating partner”, “boyfriend” , or “girlfriend”. The introductions don’t need to feel formal or heavy. An easy way to describe the person is as “my friend” and allow the outing to be exactly that- no handholding, no canoodling, just friends enjoying an easy outing. Perhaps you both choose mini golf, or ice cream, the playground, or a read aloud at the library.

The first time my fiance and I brought our girls together it was at an ice skating rink. Our then 14 year old teens with their knees knocking wobbled out together on the ice and began what would be a bit of a metaphor for their growing sistership- wobbly start, hesitant chat, giggles when one slipped, frustration as one was clearly more adept than the other.

As Jay and I watched our girls from the sidelines, secretly holding hands as they couldn’t see past the enclosure of the rink, we rejoiced that the day had come to bring our children together and also wondered what challenges would be headed our way as a result. But that’s for another blog- and glory to God we were guided through the challenges with God’s provision and protection.

For now, it is enough to recognize that this stage requires patience and discernment.

Practical Ways to Navigate Busy Schedules

Because schedules are the biggest hurdle, a little creativity can help.

A shared digital calendar is one practical tool. When both people can see school events, sports practices, and custody days, it becomes easier to spot openings without endless back-and-forth texting.

Some couples also find it helpful to:

• Plan dates further in advance rather than waiting for last-minute openings
• Be open to shorter dates, such as coffee or a walk, rather than long evenings out
• Alternate who travels if distance is involved
• Use phone calls or video chats on weeks when meeting in person is not possible

Sometimes the solution is simply flexibility.

Other times, despite the best intentions, the calendars never quite line up.

When Timing Simply Does Not Work

This part can be disappointing, but it is also honest.

If your available days never overlap with theirs, and both of you are already stretching your schedules as far as possible, it may mean the relationship has run its course. Not because anyone did something wrong. Just because the timing does not allow for the kind of connection that dating requires. True relationships must be done in person and not simply through a smartphone. You are not praying for a digital partner but one you can be in the same space with in order to feel what life with them would be like.

This is a moment for grace.

You can thank each other sincerely for the time you shared, wish one another well, and close that door without bitterness. This is easily done if no promises have been made and no intimacy shared prematurely. If you’ve both been collecting data on one another, filing away green, yellow or red flags, then this step should be a natural conclusion to your observations.

Sometimes life’s circumstances simply make a relationship difficult at the present time. Sometimes they reveal that someone else may be a better fit for this particular season.

And sometimes it simply becomes one more experience that God uses to teach us patience, clarity, and trust.

Dating as parents will never be as simple as it looks in a romance novel or a sitcom. Real life comes with school backpacks, a pet who chewed your laptop charger, early bedtimes, piles of laundry, forgotten permission slips, a lost sneaker and calendars that fill up faster than we expect.

But even in the middle of all that, meaningful relationships can grow with God’s guidance and the fruit of Holy Spirit (Galatians 5:22 “…love, joy, peace, forbearance, kindness, goodness, faithfulness, gentleness and self-control….” leading the way.