Engaged Couples Need To Talk About These Critical Topics
The champagne toasts have been made, the ring is on your finger, and your social media is flooded with congratulations. Getting engaged is thrilling, and it’s natural to dive headfirst into wedding planning—choosing between venues in Lakeview, debating invitation designs, and tasting cakes at bakeries along Broadway.
But while you’re planning the perfect wedding day, have you thought about planning for the marriage itself?
Some of the most important conversations you’ll have as a couple happen before you walk down the aisle. These discussions aren’t always easy, and they rarely come up naturally between dress fittings and honeymoon planning. But having them now, when you’re excited about your future together, can prevent misunderstandings and resentment down the road.
Here are five essential conversations every engaged couple should have before saying “I do.”
1. Money: Beyond “What’s Your Credit Score?”
Financial disagreements are one of the leading causes of marital conflict, yet many engaged couples avoid detailed money conversations. You might know your partner’s job title, but do you know their approach to money?
This conversation goes deeper than splitting rent or combining bank accounts. Talk about your financial histories, including any debt you’re bringing into the marriage. Discuss your attitudes toward money—is one of you a saver while the other is a spender? What does financial security mean to each of you?
Explore questions like: How will we handle major purchases? Will we combine finances completely, keep everything separate, or use a hybrid approach? What are our short-term and long-term financial goals? How much do we want to spend on housing in Lakeview, or are we open to moving to a different neighborhood for financial reasons?
Don’t forget to discuss the uncomfortable topics: prenuptial agreements, supporting family members financially, student loans, and how you’ll navigate financial stress. Money touches nearly every aspect of married life, from where you live to whether you have children to how you spend your weekends. Getting aligned now creates a foundation of trust and shared purpose.
2. Family: Navigating Two Worlds
When you marry someone, you’re joining their family system, and they’re joining yours. Every family has its own culture, traditions, expectations, and dynamics. Sometimes these blend smoothly; other times, they clash.
Talk honestly about your families. What role do you expect your parents and in-laws to play in your marriage? How often do you envision visiting or hosting family? What happens when family traditions conflict—whose family do you visit for major holidays?
For couples living in the Andersonville area, there may be practical questions: If your parents don’t live in Chicago, how often will you travel to see them? If they do live nearby, what boundaries do you need around spontaneous visits or family involvement in your daily life?
Discuss more sensitive topics too. How will you handle criticism from family members? What if your partner’s family has different values or lifestyles than yours? How will you present a united front when family members overstep boundaries? What happens if aging parents eventually need support or care?
Understanding each other’s family histories also helps you understand each other. The way your partner was raised shapes their expectations about everything from how to argue to how to celebrate birthdays to what “clean enough” means.
3. Children: The Big Questions
“Do you want kids?” seems like an obvious conversation for engaged couples, but it’s just the starting point. Many of our clients in Roscoe Village grapple with this question as part of preparing for marriage. If you both want children, when? How many? What if you struggle with fertility—how far are you willing to go with medical interventions, and how much are you willing to spend?
Talk about parenting philosophies before there’s a baby keeping you up at night. What kind of parents do you want to be? How were you each parented, and what do you want to replicate or avoid? Will one partner stay home with children, or will you both continue working? How will you split childcare responsibilities?
For couples who don’t want children, discuss how you’ll handle pressure from family or friends. Talk about what you’ll do if one of you changes your mind, or if an unplanned pregnancy occurs.
Consider also how children would change your Lakeview lifestyle. Would you stay in the neighborhood, or move to the suburbs for more space or different schools? How would your social life change? What values do you want to instill in your children?
There’s no single right answer to these questions, but you need to ensure you’re on the same page—or at least understand and respect each other’s perspectives.
4. Career and Ambition: Supporting Each Other’s Dreams
Your careers will shape your marriage in countless ways—from your daily schedules to where you live to how much time you spend together. Talk about your professional ambitions and how they’ll intersect with your marriage.
What does career success mean to each of you? How important is career advancement compared to work-life balance? Would either of you relocate for a job opportunity, and under what circumstances? How will you support each other through career challenges, job changes, or periods of unemployment?
Discuss practical realities: If both of you work demanding jobs in Chicago, how will you protect time together? What happens if one partner’s career takes off while the other’s stalls? How will you handle competition or resentment around career success?
For couples in Lakeview and Chicago’s North Side, there may be specific considerations. The neighborhood’s central location is ideal for professionals, but long commutes or demanding schedules can strain a relationship. How will you ensure your marriage doesn’t become just two people living parallel lives, passing each other in your apartment between work obligations?
Talk about longer-term career questions too. Does either of you want to start a business or make a major career change? How would that impact your lifestyle and financial stability? What are you working toward, both individually and as a couple?
5. Conflict: How You’ll Fight Fair
Here’s a guarantee: you will argue with your spouse. The question isn’t whether you’ll have conflict, but how you’ll handle it when it happens.
Discuss how you each approach disagreement. Do you need time to cool down, or do you prefer to talk things through immediately? What happens when you’re angry—do you shut down, raise your voice, leave the room, or become sarcastic? What does your partner do that escalates conflict, and what helps you both de-escalate?
Talk about your conflict histories. How did your parents handle disagreements? What have you learned from past relationships about productive versus destructive conflict? What are your deal-breakers in an argument—behaviors you won’t tolerate like name-calling, stonewalling, or bringing up past mistakes?
Establish ground rules for fighting fair. Maybe you agree never to threaten divorce during an argument, or to avoid discussing major issues late at night when you’re both exhausted. Perhaps you commit to taking breaks if things get too heated, with a specific plan to revisit the conversation.
Many couples in Lakeview share small living spaces, which can intensify conflict—there’s nowhere to escape when tensions are high. How will you navigate disagreements when you can’t get physical distance from each other?
Understanding how you each handle conflict now, before you’re in the middle of a major disagreement, gives you tools to work through challenges constructively.
Having These Conversations
If you’re reading this list feeling overwhelmed, that’s normal. These are big, sometimes uncomfortable conversations. Many engaged couples find it helpful to tackle them with professional support through premarital counseling, where a trained therapist can guide discussions and help you develop communication skills that will serve your marriage for years to come.
The goal isn’t to have perfect agreement on every topic—that’s unrealistic. Instead, you’re aiming for understanding, respect for each other’s perspectives, and a plan for navigating differences. You’re learning to communicate about difficult topics, which is perhaps the most valuable skill in any marriage.
These conversations also aren’t one-and-done. Your perspectives will evolve as you grow together. The financial plan you make as newlyweds may need adjusting when one of you wants to change careers. Your ideas about parenting will deepen when you’re actually holding your baby. The key is establishing a pattern of open, honest communication now.
Moving Forward Together
Wedding planning focuses on one day—the flowers, the food, the first dance. But marriage is about all the days that come after. Having these five essential conversations helps ensure you’re not just planning a beautiful wedding, but preparing for a strong, resilient marriage.
As you walk through Lakeview together, stopping for coffee or browsing the farmers market, you’re building a shared life. These conversations help you understand what that life will look like, what challenges you might face, and how you’ll face them together. They transform your engagement from a countdown to a wedding into a launching point for a partnership built on honesty, understanding, and mutual respect.
That foundation—far more than any wedding detail—is what will carry you through the decades ahead.
