The Date Challenge
The Date Challenge for Engaged and Married Couples
I give nearly every engaged couple a simple homework assignment called the Date Challenge.
When I first meet a couple, their wedding is usually a few months to a year away. Excitement fills the air. They’re busy booking vendors, comparing venues, picking colors, gathering ideas, making spreadsheets, downloading apps, talking about flowers, choosing songs, and answering questions they never expected. After the proposal, sometimes within hours, couples turn into an event-planning team.
This is completely understandable. Weddings require a lot of planning, with real decisions, deadlines, and money involved. But during this busy season, it’s easy for couples to focus so much on the event that they lose sight of their relationship. Getting ready for a wedding and getting ready for marriage are connected, but each is different. A wedding is a beautiful, meaningful day filled with formal clothes, flowers, photos, cake, music, and lots of people figuring out where to stand. Marriage is the start of life together after the celebration. That’s why couples need to pay attention to their relationship during the engagement. They still need laughter, connection, fun, good conversations, and time together that isn’t about the seating chart. Wedding planning can take over if you let it, so I encourage couples to be intentional.
Getting ready for a wedding and getting ready for marriage are connected, but each is different. A wedding is a beautiful, meaningful day filled with formal clothes, flowers, photos, cake, music, and lots of people figuring out where to stand. Marriage is the start of life together after the celebration.
That’s why couples need to pay attention to their relationship during the engagement. They still need laughter, connection, fun, good conversations, and time together that isn’t about the seating chart. Wedding planning can take over if you let it, so I encourage couples to be intentional.
The Date Challenge has four rules.
Rule 1: Go on One Date Every Week
This rule might seem obvious, but the key is to actually plan the date.
Dating usually starts a relationship. You ask someone out, make plans, spend time together, share stories, and slowly build a connection. Dating brought you together, and I believe it’s a habit that helps keep you together.
You can go on more than one date a week if you like, but the challenge is to plan at least one. If couples go more than a week without setting aside intentional time together, the relationship can start to feel strained. Many couples see each other daily, but seeing each other isn’t the same as spending meaningful time together. This is one of the big illusions of daily life. Couples often think, “We’re together all the time.” But doing chores, running errands, or sitting next to each other while scrolling on your phones isn’t the same as going on a date. If your relationship is only about chores and obligations, time together can start to feel like a duty instead of something special. This is one of the big illusions of daily life. Couples often think, “We’re together all the time.” But doing chores, running errands, or sitting next to each other while scrolling on your phones isn’t the same as going on a date.
If your relationship is only about chores and obligations, time together can start to feel like a duty instead of something special.
A date can be simple: dinner, coffee, a walk, a movie, a game night, a picnic, a trip to the bookstore, a local event, a museum, a hike, or dessert after dinner. What matters most is being intentional, not extravagant. Put your date on the calendar. Treat it like it matters, because it really does. Put your date on the calendar. Treat it like it matters, because it really does.
Rule 2: No Wedding Talk on Date Night
For engaged couples, this is the rule that matters most: No wedding talk on date night.
This rule speaks directly to the tension between event planning and relationship building. Once the wedding planning begins, it is easy for every conversation to drift back to the wedding. Even when couples want to talk about something else, the wedding is always on their minds. There is always one more decision, one more vendor, one more question, one more family dynamic, one more payment, one more item on the list.
The wedding can start to feel like a third person in the relationship, and it’s not always a quiet guest.
So, one night a week, set wedding planning aside. Leave the folder at home, keep the apps closed, and don’t talk about the guest list, flowers, budget, rehearsal, music, seating chart, or whether someone’s cousin should be invited. Spend one evening just enjoying being together as a couple, without thinking about the event. For married couples, you can personalize this rule. It becomes “No ______ Talk.” Fill in the blank with whatever topic usually takes over your conversations, such as work, kids, money, house projects, conflicts, or schedules. These things matter, but date night is a chance to step away from them and just enjoy each other’s company.
For married couples, you can personalize this rule. It becomes “No ______ Talk.” Fill in the blank with whatever topic usually takes over your conversations, such as work, kids, money, house projects, conflicts, or schedules. These things matter, but date night is a chance to step away from them and just enjoy each other’s company.
There’s a time for those conversations. I even encourage couples to hold a weekly business meeting to discuss schedules, tasks, and other topics. But date night is different. It’s for enjoying each other, not for fixing problems.
Rule 3: Alternate Who Plans Date Night
One reason date night fades away is that it often turns into just one person’s responsibility.
Traditionally, planning dates has often been the guy’s job. No offense to the guys, but most have two or three good date ideas, and they’ve probably used them already. After that, it’s easy to fall back on the phrase that ends creativity in many relationships: “I’ll do whatever you want to do.”
That might sound flexible or even thoughtful, but most of the time, it just shifts the planning burden to the other person.
Couples can also fall into a rut together—same restaurant, same order, same show, same routine. There’s nothing wrong with favorite places and comfortable habits, but dating should still involve some thoughtfulness and effort.
To avoid this, take turns planning date night. One week, one partner plans; the next week, the other does.
There are a few extra guidelines. First, whoever is planning the date shouldn’t rely on their partner to make all the decisions. It’s fine to ask about schedules, budget, or basic preferences, but don’t ask your partner to plan the date for you. Second, the person who didn’t plan the date shouldn’t overrule the plan. Unless the date is truly unsafe, morally wrong, or involves a restaurant where you once got food poisoning, just go with it.
This is about sharing the effort. Dating shouldn’t be one person’s job forever. When both people take turns planning, you both practice paying attention. You learn what your partner enjoys, think creatively, and look for ways to make them happy. Becoming a student of the person you love is a great habit for marriage.
Rule 4: Ask the Question
The final rule is called Ask the Question. The question is simple: “Will you go out with me?”
It is simple: “Will you go out with me?”
Once a couple is together, engaged, living together, or married, this question often fades away. We start to assume the other person will join us, is available, or knows what we mean. We assume the relationship doesn’t need the language of pursuit anymore.
Assuming things is comfortable, but it can also be risky. It can start to feel a lot like taking someone for granted.
Even though engagement starts with someone asking the big question, couples still need to ask smaller questions along the way. “Will you go out with me?” might seem simple, but it means more than we think. It says, “I’m choosing you again. I want your company. I want to spend time with you. I’m not assuming I have access to your heart just because we’re already together.”
Every romantic comedy centers on some version of this question. We don’t just want to know if the couple will end up together—we want to see how they ask, how they respond, and how the pursuit unfolds. That same dynamic matters in real relationships too.
So ask the question. Ask in person, with a note, or even by text if needed, but don’t let your relationship run on assumptions. There’s something special about being invited, even by someone who already loves you.
Why the Date Challenge Matters
The Date Challenge isn’t about adding another task to your busy life. It’s about choosing each other on purpose.
Couples who keep dating tend to stay connected. They keep making memories, laughing, learning about each other, and creating space for their relationship to grow. This is especially important during engagement, when the wedding can take over, and in marriage, when daily life can make romance seem less important.
The challenge is easy to remember:
Go on one date every week.
No Wedding Talk or problem topics on date night.
Alternate who plans the date night.
Ask, “Will you go out with me?”
Start this week.
The Date Challenge is a small habit that helps couples keep choosing each other long after the proposal, the wedding day, and as life gets busy. It’s a simple way to keep your relationship strong, even when life is full.
Download the Free Date Night Questions Guide
Want help starting better conversations on your next date? I created a free guide called 75 Great Questions to Ask on Date Night. It is designed for engaged and married couples who want to laugh, remember, learn, and stay connected. The guide includes questions about childhood, family, identity, values, marriage, fun, favorites, faith, conflict, and the future.
Download the free Date Night Questions and our Full Wedding Chaplain Resource Library
Enter your email, and I will send the packet directly to your inbox.
Pick five to ten questions, go on a date, and keep choosing each other on purpose.
Image: Tima Miroshnichenko
Image: Doug Scheetz
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