Pre-Engagement: Questions to Discuss Before You Say "Yes!"

While the sparkle of a ring and the joy of celebration are certainly part of the process, getting engaged signifies so much more. It's a commitment to a shared future and a decision to embark on a lifelong journey with your partner – for better or for worse.
If you're reading this, you're likely a little Type-A and want to seek a thoughtful approach to this momentous step. You obviously crave that romantic "yes!" moment, but also want to ensure a strong foundation for your future together.
And that's where pre-engagement conversations come in.
Beyond the butterflies and fireworks, it's crucial to align on key aspects of your lives. Discussing your goals, dreams, finances, and values might not seem like the most romantic endeavor, but it's certainly preferable to discovering fundamental differences down the road and joining the divorce rate percentage.
So, how do you approach these important conversations?
1. Start with a Date Night
Yes, you read that right! Set the stage for open and honest communication by creating a comfortable and relaxed atmosphere. Enjoy your favorite meal, pour a glass of wine, and prepare to connect on a deeper level.
While spontaneity is lovely, springing a conversation about your future onto an unprepared partner might not be the most welcomed approach. Ensure you're both at a stage where engagement feels imminent and you're ready to delve into these meaningful discussions.
Planning a date night specifically to explore your future together might seem a bit unconventional, but it demonstrates a deep commitment to building a strong and lasting relationship. It's an opportunity to connect on a profound level, setting the stage for a lifetime of shared dreams and aspirations.
To help guide your conversation, we've compiled a list of essential questions to explore together. Think of it as your roadmap to a fulfilling and successful partnership.

Essential Questions for Couples:
- Finances
- How do you currently manage your finances individually and as a couple? How do you plan to change (or not change) those systems in marriage?
- What are your financial goals (e.g., saving, investing, homeownership)?
- How will you handle debt and joint expenses?
- Lifestyle
- Where do you envision yourselves living in the long term?
- What are your preferences for housing, travel, and leisure activities?
- How do you prioritize work-life balance and personal time?
- Family and Children
- Do you both want children? If so, how many and when?
- What are your views on parenting styles and family values?
- How will you handle extended family relationships and potential conflicts?
- Values and Beliefs
- What are your core values and beliefs (e.g., religion, ethics, politics)?
- How do you approach decision-making and problem-solving?
- What are your expectations for roles and responsibilities in the relationship?
- Conflict Resolution
- How do you typically handle disagreements and conflicts?
- Are you comfortable expressing your needs and concerns openly and respectfully?
- Are you willing to seek professional help if needed?
- Past & Future
- Have you discussed any significant past experiences that might affect your relationship? (e.g. family issues, trauma, previous relationships, etc.)
- What are your individual and shared dreams for the future?
- What are your expectations for personal growth and development within the relationship?
And finally, the most important question:
- Why do you want to marry each other?
Creating a Safe Space for Honest Conversations
It's understandable if you're feeling a bit overwhelmed after reviewing the suggested conversation topics. Open and honest communication can be challenging, even in the best of relationships. Here are a few tips to keep in mind:
- Approach each other with empathy and understanding. Remember that you're on the same team, and the goal is to strengthen your connection, not to win an argument.
- Create a dedicated space for these conversations. Minimize distractions and ensure you both have ample time to express yourselves fully. (And ensure you’ve got nibbles—these conversations are especially hard when you’re hangry!)
- Use "I" statements to share your feelings and perspectives without assigning blame. This helps foster a safe and non-judgmental environment.

Seeking Pre-Engagement Counseling
If you're still feeling overwhelmed, but recognize the value of these conversations, consider seeking the guidance of a qualified professional. Many couples find it beneficial to have a neutral third party help facilitate these discussions. A therapist or counselor can provide you with valuable tools and strategies for navigating these and future conversations, ensuring healthy and productive communication within your marriage.
Here’s what one of our HCTG staff members, Caroline, has to say about her pre-engagement counseling experience:
“We chose a married couple who we looked up to and had experience in counseling others through pre-marital conversations. They gave us tons of incredible advice, helped jump-start conversations we needed to have, and also developed a relationship with us so we feel comfortable reaching out to them in the future.
We walked away feeling so confident in the decision we were making and already knew how we were going to approach mundane things like the dishes, along with big things like how to handle conflict within our respective family units. Walking into marriage with these newfound tools and methods has proven invaluable to us as we’ve navigated almost five years of marriage!”
You Can Do This!
In all of this, we should not forget the most important question: Should we get married?
The importance of these pre-engagement discussions cannot be overstated—this is what builds a strong foundation for a whole-hearted “yes!!!!!” when you or your partner pops the question, and for the duration of your engagement.
Once you’ve gone through these conversations, as time-consuming and potentially awkward as they can be, you’ll find yourself with a greater appreciation for your partner and the journey ahead. So if you couldn’t tell already, we 10000000/10 recommend pre-engagement conversations!
Oh, and after the questions have been answered and the ring is on (or incoming!), be sure to come on back to Here Comes The Guide to plan your big day!
If you found success with the pre-engagement conversation and are looking for next steps, check out some of our other resources:

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