101 Questions to Ask Before You Get Engaged

So, you’re in love. Maybe you’ve been dating for a while, maybe it feels like forever. You’re thinking about the next step getting engaged. And honestly, it’s exciting. The Pinterest boards. The ring shopping. The dreamy conversations about “our future house.”

But here’s the real question: do you actually know this person well enough to tie your whole life to theirs?

Funny thing is, most couples don’t sit down to talk about the stuff that really matters before saying “yes.” They talk about vacations, dream weddings, maybe kids. But what about debt? Religion? Politics? Even silly things like who does the laundry, or how often do you need alone time?

That’s where this list of 101 questions comes in. It’s not about grilling your partner like a detective. It’s about learning how the two of you work together when life gets messy.

The Core Problem / Challenge

Here’s the truth: love is not enough.

I know, it sounds harsh. Movies sell us the idea that passion can conquer anything. That if two people are meant to be, they’ll just figure it out. But let’s be honest. Passion doesn’t pay bills. It doesn’t magically fix conflicts about parenting or in-laws. And it definitely doesn’t teach you how to talk about money without fighting.

A lot of people rush into engagement because they think marriage will “fix” their relationship. It won’t. In fact, it often magnifies what’s already broken.

I used to believe arguments about chores or different schedules were just “normal couple stuff.” But small cracks, left unchecked, can become canyons.

Research & Psychology Insights

Psychologists often emphasize that the best predictor of marital success isn’t how much you love each other it’s how well you communicate. Dr. John Gottman, a famous marriage researcher, studied couples for decades and found that it’s not about avoiding conflict. It’s about how you handle it.

Here’s another stat: according to the American Psychological Association, about 40–50% of marriages in the U.S. end in divorce. That’s not to scare you, but to highlight the importance of asking tough questions before you say “I do.”

Money, sex, children, values those are the big four areas where most couples clash. If you don’t talk about them now, you’re basically building a house without checking if the foundation is cracked.

Actionable Steps / Solutions

So how do you actually do this?

Set the tone. Don’t make it an interrogation. Frame it like, “I want us to know each other better before we make this huge decision.”
Pick the right moment. Not after a fight. Not when you’re both stressed. Maybe on a walk, over coffee, or during a road trip.
Start small. Begin with fun, lighthearted questions. Then move into deeper, sometimes uncomfortable topics.
Listen. Don’t just wait for your turn to talk. Really hear what your partner is saying even if it’s not what you expected.

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Wrong approach: “Do you want kids? Because if not, I don’t see a future with you.”
Better approach: “I’ve been thinking about parenting. How do you feel about having kids someday?”

101 Questions to Ask Before You Get Engaged

Alright, let’s get into it. I’ve broken these down into categories because asking all 101 in one sitting would be… overwhelming.

Personal Values & Beliefs

What does marriage mean to you?
Do you believe marriage is forever?
How do you handle personal growth alone or together?
How do you feel about religion and spirituality in your life?
Do you want your partner to share your faith?
What role does honesty play in your relationships?
Are there things you consider “deal-breakers”?
How do you define loyalty?
What does forgiveness look like to you?
Do you believe in keeping secrets from each other?

Money & Finances

How do you feel about debt?
Do you budget?
Are you a spender or saver?
Do you expect joint or separate bank accounts?
How do you feel about financial independence in marriage?
Do you believe in lending money to family or friends?
What’s your view on investing?
How do you handle financial stress?
Do you think money equals security?
How much do you think a couple should share about their income?

Family & Children

Do you want kids?
If yes, how many?
What values would you want to pass on to them?
What parenting style do you believe in?
How do you feel about adoption?
How should discipline work in a household?
How do you picture holidays with kids?
Do you think kids should be raised religiously?
How do you feel about extended family’s role in raising children?
What fears do you have about parenting?

Daily Life & Household

Do you cook or prefer takeout?
How important is cleanliness to you?
Who does laundry in your dream household?
Do you prefer structure or flexibility in daily life?
How do you feel about pets?
What’s your ideal morning routine?
Night owl or early bird?
How do you recharge after a long day?
What kind of home environment makes you happiest?
How do you divide chores fairly?

Sex & Intimacy

How important is sex in a marriage to you?
How often do you expect intimacy?
Do you believe in monogamy as absolute?
How do you handle mismatched sex drives?
Are you comfortable talking about fantasies?
How do you handle rejection in intimacy?
How do you feel about public displays of affection?
What role does physical touch play in your life?
How do you deal with stress affecting intimacy?
Do you believe emotional intimacy is more important than physical?

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Conflict & Communication

How do you argue calm or fiery?
Do you hold grudges?
How do you apologize?
Do you shut down or talk things out?
How important is tone of voice in conflict?
Do you believe in going to bed angry?
How do you feel about therapy or counseling?
What’s your biggest communication weakness?
Do you need space after arguments?
How do you rebuild trust after conflict?

Lifestyle & Dreams

Where do you want to live long-term?
City life or country life?
How important is travel to you?
What’s your dream vacation?
Do you want to live near family?
How important is career success to you?
Do you want to own or rent a home?
What’s your biggest life goal?
Do you believe in retirement planning?
How do you define “success”?

Future Planning

Do you want kids right away or later?
What’s your view on retirement savings?
Where do you want to live when you’re old?
How do you want to handle aging parents?
Do you want to create a will?
What kind of lifestyle do you want in 10 years?
How do you feel about job relocation?
Do you want to travel after retirement?
How do you feel about risk-taking vs. stability?
What’s your ultimate dream for your life together?

Random but Important

What’s your love language?
How do you celebrate small wins?
What scares you most in life?
What do you want people to say about us as a couple?
How do you deal with disappointment?
Do you believe in personal space in marriage?
How do you handle illness or bad health?
What role do traditions play in your life?
What makes you feel most supported?
How do you feel about therapy or self-help books?
What’s one question you wish I asked but didn’t?

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Real-Life Scenarios

Imagine this: you’re married, it’s been three years, and you discover your partner has $30,000 in student loans they never told you about. That’s not just a surprise it’s a betrayal. And yet, it happens all the time.

Or picture this: one of you wants kids in two years, the other wants to wait ten. You can love someone deeply and still be on totally different life paths.

These questions aren’t about killing romance. They’re about protecting it.

Comparison Table: Talking vs. Not Talking

Situation	Without Asking	With Asking
Finances	Hidden debt, fights	Shared plans, less stress
Kids	Huge disagreements	Aligned expectations
Intimacy	Resentment	Openness, closeness
Family	Clashes with in-laws	Agreed boundaries
Lifestyle	Misaligned dreams	Shared goals

Myths & Misconceptions

Myth: “If we’re in love, everything else will work out.”
Truth: Love helps, but communication sustains.
Myth: “Asking too many questions kills the romance.”
Truth: Real intimacy comes from honesty.
Myth: “People change after marriage, so why bother?”
Truth: Yes, people evolve. But knowing their values gives you a compass.

Emotional & Lifestyle Angle

If you’ve ever felt scared about bringing up tough topics, you’re not alone. Most of us avoid them because they feel… heavy. But avoiding them doesn’t make them go away.

Asking questions is not about doubting your love it’s about strengthening it. Think of it like training before a marathon. You don’t just show up at the starting line. You prepare.

Future Strategies / What’s Next

Heading into 2025, relationships face new challenges: remote work blurs boundaries, financial instability adds stress, and technology changes how couples connect. It’s more important than ever to build strong foundations before getting engaged.

Try journaling your answers separately, then comparing them. Or even use apps designed for couples to spark conversations. Don’t be afraid of awkward pauses they usually mean you’re touching on something real.