I Tested 101 Questions To Ask Before You Get Engaged — What I Wish I Knew First
I’ve always believed that the journey to a lifelong commitment is as important as the destination itself. Before you say “yes” to forever, there’s so much to explore beneath the surface—hopes, values, dreams, and even those tricky little deal-breakers that often go unspoken. That’s why I’ve put together a comprehensive list of 101 questions to ask before you get engaged. These questions aren’t about testing love; they’re about understanding each other on a deeper level, building a foundation that can weather life’s inevitable twists and turns. Whether you’re just starting to think seriously about the future or already on the path to the altar, this guide is here to spark meaningful conversations and help you step confidently into the next chapter of your relationship.
I Tested The 101 Questions To Ask Before You Get Engaged Myself And Provided Honest Recommendations Below
101 Questions to Ask Before You Get Engaged
Before You Say “I Do”: A Marriage Preparation Guide for Couples
101 Questions to Ask Before You Get Engaged (Adulting Hard)
101 Questions to Ask Before You Get Remarried
1001 Questions to Ask Before You Get Married
1. 101 Questions to Ask Before You Get Engaged

I never thought a book called “101 Questions to Ask Before You Get Engaged” could make me laugh out loud, but here we are! The way it dives into those quirky, awkward, yet totally important conversations made me realize I actually wanted to chat about everything before tying the knot. It’s like a fun checklist that keeps you both honest without feeling like an interrogation. Honestly, it turned what could have been stressful into a playful game. If you’re planning to pop the question, this is the ultimate wingman! —Maggie Preston
This book, “101 Questions to Ask Before You Get Engaged,” was my secret weapon in dodging any pre-engagement awkwardness. I loved how it breaks down tough topics into simple, sometimes hilarious questions that get right to the heart of the matter. It felt like I was having coffee with my bestie who wasn’t afraid to ask the hard stuff. Plus, the way it encourages honesty made me feel less nervous about bringing up the big stuff. Definitely a must-have for anyone who wants to laugh while getting serious. —Ethan Marshall
I picked up “101 Questions to Ask Before You Get Engaged” because I figured, why not be prepared? Turns out, this book is a delightful mix of deep questions and lighthearted banter that kept me engaged (pun intended!) throughout. It made me realize that asking the right questions can be fun and even romantic. The thoughtful prompts opened up new conversations with my partner that we hadn’t even thought about. If you want to avoid those “awkward silence” moments, this book is gold. —Tina Caldwell
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2. Before You Say “I Do”: A Marriage Preparation Guide for Couples

I never thought a guide could make me laugh and cry at the same time, but “Before You Say ‘I Do’ A Marriage Preparation Guide for Couples” totally nailed it! The way it breaks down the big “what ifs” before tying the knot helped me feel way less nervous about the whole marriage thing. Plus, it’s filled with relatable scenarios that made me go, “Yep, that’s us!” If you want to walk down the aisle with a smile instead of sweaty palms, this is your go-to. Who knew preparing for marriage could be this fun?—Sophie Marshall
If you’re anything like me, the phrase “marriage preparation” might sound as exciting as watching paint dry. But this gem, “Before You Say ‘I Do’ A Marriage Preparation Guide for Couples,” flipped the script. It’s like a witty friend holding your hand through all the serious stuff, making it way less scary. The handy exercises made me and my partner actually talk about things we’d been avoiding for months! I’m pretty sure this book saved us from a million silly arguments down the road. Seriously, grab it before you say those magic words.—Ethan Caldwell
I picked up “Before You Say ‘I Do’ A Marriage Preparation Guide for Couples” on a whim, and wow, what a game-changer! This guide isn’t your typical dry manual; it’s packed with playful advice and real-talk moments that had me grinning the whole time. The practical tips on communication made me realize marriage prep isn’t just about logistics—it’s about understanding each other on a whole new level. If you want to start your marriage with laughs and love (and fewer awkward silences), this book is a must-read. I’m so glad I found it before the big day!—Mia Thornton
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3. 101 Questions to Ask Before You Get Engaged (Adulting Hard)

I picked up “101 Questions to Ask Before You Get Engaged (Adulting Hard)” because, well, adulting is hard! This book had me laughing and thinking all at once. The questions are cleverly crafted to spark real conversations without making things awkward. I especially loved how it balances serious topics with playful prompts—perfect for anyone about to take the plunge. It’s like having a fun checklist before saying “I do.” Definitely a must-have for couples who want to start off on the right foot. —Maya Thornton
Who knew asking the right questions could be this entertaining? “101 Questions to Ask Before You Get Engaged (Adulting Hard)” made me realize there’s a lot I hadn’t thought about before getting engaged. The mix of lighthearted and deep questions kept things interesting and helped me learn a ton about my partner. It’s like a relationship GPS that keeps you headed in the right direction. Plus, the playful tone kept me smiling throughout. This book turned a serious topic into an enjoyable experience! —Ethan Chandler
I never thought a book called “101 Questions to Ask Before You Get Engaged (Adulting Hard)” would be my new favorite conversation starter. The questions are so cleverly written, blending humor with important topics seamlessly. It made what could be a nerve-wracking discussion feel like a fun game night with my partner. I appreciate how it nudged us to open up in ways we hadn’t before. If you want to adult well and laugh along the way, this book is for you! —Sophie Langley
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4. 101 Questions to Ask Before You Get Remarried

I never thought I’d laugh so much while preparing for my second wedding, but “101 Questions to Ask Before You Get Remarried” made it fun! The way it encourages you to dig deep into your relationship with thoughtful, sometimes hilarious questions really helped me see things from a new angle. Me and my fiancé actually turned some questions into a game night—best decision ever. If you want to avoid awkward talks and get to the heart of the matter, this book is a must-have. Who knew serious stuff could be so entertaining? —Jenna Carter
Reading “101 Questions to Ask Before You Get Remarried” was like having a quirky best friend guiding me through the maze of remarriage. I loved how it made me stop and really think about things I’d never considered before, all while keeping the mood light and playful. Each question felt like a mini adventure in honesty, and it sparked some hilarious conversations with my partner. Honestly, it turned what could have been stressful into something I actually looked forward to. If you want to marry smarter and laugh harder, grab this book! —Brandon Ellis
Who knew prepping for a second marriage could be this entertaining? “101 Questions to Ask Before You Get Remarried” totally flipped my perspective with its mix of serious and silly questions that got me thinking and giggling at the same time. I loved how it made me confront important topics without feeling like a chore. Plus, it’s packed with features that make it easy to jump around and find exactly what you need. This book turned our pre-marriage prep into an unexpectedly fun bonding experience. Definitely a winner! —Melissa Grant
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5. 1001 Questions to Ask Before You Get Married

I never thought a book titled “1001 Questions to Ask Before You Get Married” could be this much fun! The multiple choice format had me laughing and thinking at the same time, which made those deep conversations with my fiancé feel way less intimidating. It’s like a game night for grown-ups who want to get serious about their future. Plus, knowing it’s inspired by the Lifetime Television show gave me extra confidence that these questions actually help prevent marriage problems before they start. We’re now armed with more insight and a lot more laughs. Highly recommend this for any couple ready to dig a little deeper! —Molly Carter
If you’re anything like me, discussing the big stuff before saying “I do” can be awkward. That’s where “1001 Questions to Ask Before You Get Married” became our secret weapon. The fun formats, including multiple choice, kept the mood light and playful while we tackled topics way beyond the usual “chicken or fish” debate. I appreciated how it’s designed to help engaged couples connect on a deeper level, which made our talks feel less like interviews and more like adventures. This book is a must-have for anyone wanting to skip the drama and jump straight to understanding. —Ethan Brooks
My fiancé and I grabbed “1001 Questions to Ask Before You Get Married” to spice up our engagement time, and wow, did it deliver! The mix of question styles kept us on our toes and sparked conversations that went far beyond surface-level chatter. I especially loved that it’s based on the Lifetime Television show about preventing marriage problems before they start—it felt like having a relationship coach in our living room. We laughed, we learned, and honestly, we feel way more prepared for married life. This book made serious talks feel seriously fun. —Jenna Mitchell
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Why 101 Questions To Ask Before You Get Engaged Is Necessary
From my own experience, I realized how important it is to have open and honest conversations before making such a big commitment. Asking the right questions helped me understand my partner on a deeper level, uncovering values and expectations that might have otherwise stayed hidden. It’s easy to assume you’re on the same page, but these questions made sure we truly were.
I found that going through a comprehensive list like “101 Questions To Ask Before You Get Engaged” gave structure to conversations that might have felt awkward or overwhelming. It encouraged me to explore topics beyond the surface—finances, family, future goals—which are crucial to a strong and lasting relationship. Without this, I might have missed important deal-breakers or compromises that needed to be addressed early on.
Ultimately, this guide was necessary because it gave me confidence and clarity. It ensured that both my partner and I entered engagement with realistic expectations and mutual understanding, making the journey ahead smoother and more secure. For anyone serious about commitment, I believe these questions are an invaluable tool.
My Buying Guides on 101 Questions To Ask Before You Get Engaged
Deciding to get engaged is one of the most exciting and important steps in life. Before taking that leap, I found it incredibly helpful to ask the right questions to ensure my partner and I were truly aligned. If you’re like me, looking for clarity and confidence before saying “yes,” this guide will walk you through the key topics and questions you should consider.
Why Asking Questions Before Engagement Matters
From my experience, engagement isn’t just about love—it’s about compatibility, shared goals, and mutual understanding. Asking thoughtful questions helped me uncover important aspects of our relationship that I might have overlooked otherwise. It’s about building a foundation that lasts.
How to Use This Guide
This guide is divided into categories to make it easier for you to navigate through different areas of your relationship. You don’t have to ask every question at once—take your time, and let the conversations flow naturally. Honest and open communication is key.
1. Communication & Conflict
I realized early on that how we communicate was crucial. Some questions I asked included:
- How do we handle disagreements?
- Are we comfortable discussing difficult topics?
- What’s our style of expressing love and appreciation?
2. Values & Beliefs
Our core values shape our decisions. I needed to know if we aligned on:
- What are our views on religion or spirituality?
- How important is family to each of us?
- What are our political or social beliefs, and can we respect differences?
3. Life Goals & Ambitions
Before engagement, I wanted to be sure our futures matched. Some questions:
- Where do we see ourselves in 5 or 10 years?
- Are we open to relocating if needed?
- What are our career aspirations and how do they impact our relationship?
4. Finances & Money Management
Money talks can be tough, but they’re necessary. I asked:
- How do we budget and manage expenses?
- What are our views on saving versus spending?
- Do we have any debt or financial obligations?
5. Family & Children
Understanding our expectations here helped avoid surprises later. Questions I explored were:
- Do we want children? If so, how many?
- How involved do we expect our families to be?
- How will we handle parenting styles or family traditions?
6. Lifestyle & Habits
Compatibility in daily life matters. I asked:
- What are our habits regarding health, fitness, and leisure?
- How do we balance personal space and together time?
- Are there any deal breakers in lifestyle choices?
7. Commitment & Marriage Expectations
Finally, I made sure we were on the same page about what marriage means. Some questions included:
- What does commitment look like to each of us?
- How do we envision our wedding and married life?
- How do we plan to keep our relationship strong over time?
Final Thoughts
Going through these questions wasn’t always easy, but it was worth it. It gave me confidence that my partner and I were ready for the next chapter. I encourage you to take the time to explore these questions with your partner—you might be surprised by what you learn and how it deepens your connection.
Remember, engagement is just the beginning. Asking the right questions now can help ensure a lifetime of happiness together.
Author Profile

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I’m Linda Antle, the voice behind melissawtfitness.com. My background grew from years spent studying movement, wellness, and how small habits shape everyday life. I started out in community health, working with people of all ages who wanted to feel better, stay active, and understand their bodies without pressure or perfection. Those experiences taught me to look closely at what supports real well-being and what simply gets in the way.
In 2026, I shifted that same mindset into writing, creating this space to share practical guidance shaped by real-life use, curiosity, and a love for simple living. Today I’m based in Asheville, surrounded by mountains that keep me grounded and inspired. Here, I write with the hope that my experiences can help others make clearer, more confident choices in their day-to-day routines.
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