Ask Alison: Dating Etiquette For Women Who Know What They Want

We’ve all heard the rules: don’t talk about money, politics, religion, sex, or health, especially not on a first date, because they’re too intense, too personal, too likely to scare someone off.

But what if avoiding them is exactly what’s keeping us from the kind of connection we’re actually looking for?

If you’re dating with the hope of building a life, and not just passing time, there comes a point when avoiding these conversations becomes less polite and more counterproductive. Because when something truly matters to you—your faith, your desire for children, your values around marriage, money, or even wellness—it’s not “too much.” It’s essential.

Not every first date needs to feel like a job interview. But when a woman knows what she wants, she doesn’t need to apologize for asking honest questions. In fact, having the courage to go there, kindly and with discernment, isn’t just good etiquette. It’s a sign of respect.

So how soon is too soon to talk about the serious stuff? What’s the difference between being transparent and oversharing? And how do you bring it up in a way that invites connection rather than conflict, without spiraling into a full Andy Anderson in How to Lose a Guy in Ten Days moment?

Let’s talk about it.

There’s No One-Size-Fits-All, But There Is a Guiding Principle

There’s no universal formula for when to talk about the “big things.” Every relationship has its own pace, and every person carries different priorities. But if there’s one principle that should guide your timing, it’s this: wholehearted respect for the other person and for yourself.

That means respecting the other person’s comfort level, time, and emotional investment. And it also means honoring your own values and being brave enough to say what matters to you. Dating with intention requires discernment: knowing when to speak up, when to listen, and when to walk away if something just isn’t a fit.

When in doubt, it helps to remember this simple etiquette framework: share before you ask.

If you open up first, even briefly, it creates a natural invitation. It softens the moment and makes the question feel less like a spotlight and more like a shared reflection. 

And while that might sound simple, it’s rooted in real relationship wisdom. Research from the Gottman Institute shows that emotionally intelligent communication and mutual influence are among the strongest predictors of long-term relational success.

Instead of asking, “Do you want kids?”, you might say: “I’ve always pictured myself as a mom someday, so that’s something I’m thoughtful about when I’m dating. Is that something you’ve thought about too?”

It’s a small shift, but a powerful one. Suddenly, the conversation isn’t a pop quiz; it’s a window into who you are and what you care about.

What to Bring Up And When

While there’s no perfect timeline, there are natural opportunities to talk about important topics. Here’s how to recognize those moments without forcing them:

Early Days: The First Few Dates

Your goal here isn’t to lay your entire life story on the table, but to gently introduce the values that shape you.

If faith is a cornerstone of your life, it’s okay (and even wise) to mention that early on. If you know you want marriage and children one day, say so. Not in a “let’s name our future kids” way, but in a “this is the direction I’m heading” kind of way.

Some examples:

• “Sundays are sacred for me. I usually go to church and unplug for the day.”

• “I deleted the apps for a while, but I came back because I realized I do really want to meet someone I can build a life with.”

Let your actions and small comments paint a picture. People pick up more than you think.

The Getting-to-Know-You Phase: A Few Weeks In

Once you’ve established some rapport, you can start going deeper. Maybe a date-night conversation turns more personal; this is a good moment to bring up things like past experiences, views on family, or even lifestyle preferences.

As relationship therapist Esther Perel often notes, early romantic connection isn’t just about chemistry, it’s about pacing. For a charming reminder of how respect and confidence go hand in hand, this French-inspired dating etiquette piece offers timeless tips that still resonate today. “The art of intimacy,” she writes, “is learning how to create the right conditions for deeper conversation over time.” In other words, timing isn’t just about caution, it’s about care.

So let your questions grow from real curiosity. And if you need a gentle nudge that etiquette isn’t about rules, it’s about rhythm, this list of forgotten dating manners is full of gracious reminders worth reviving.

You could ask:

• “Do you come from a big family?”

• “Was marriage modeled well for you growing up?”

• “How do you usually handle conflict when something’s bothering you?”

And again, share first.

• “I used to avoid conflict at all costs, but I’ve learned that working through it can actually bring people closer. How about you?”

The tone here matters just as much as the content. Grace, not judgment. Curiosity, not control.

When Something Is Important to You

Timing isn’t always about the calendar, it’s about emotional clarity. If something is weighing on your heart, it’s okay to bring it up sooner rather than later.

Maybe you’re managing a chronic illness. Maybe you’ve been through a difficult breakup. Maybe your politics or views on family roles are non-negotiables. Those aren’t “third date” or “fifth date” topics. They’re whenever-you’re-ready-but-don’t-hide-it-too-long topics.

Here’s the rule: if not talking about it is making you feel like you’re performing instead of showing up as yourself, it’s time.

And you can say it with kindness: “This might feel a little personal, but I’ve found it’s better to be honest early on; I’ve been through something that shaped me a lot, and I want to share it.”

When Silence Isn’t Polite, It’s a Misstep

Women who date with intention hold respect close to their own time and energy, and to the heart of the person sitting across from them. Ironically, avoiding important conversations early on can feel polite in the moment, but often leads to confusion or quiet resentment down the line.

• Wasted time: Putting off the real stuff can seem respectful… until you discover months in that your partner doesn’t share your core beliefs. Studies show online daters are increasingly frustrated by this “choice overload.” 45% say app fatigue sets in when they swipe endlessly with no real substance.

• Emotional distancing: Research from the University of Georgia links how couples resolve conflict to both relationship stability and physical health. Avoiding vulnerable conversations might feel like a reprieve, but it can actually create stress, not peace.

• Deeper clarity: In long-term relationships, psychologists have found that listening well, addressing conflict early, and communicating expectations honestly are key to lasting love.

In other words, silence isn’t always sweet. Sometimes, it keeps you from being seen, and from truly seeing someone else.

If you consider yourself a values-driven dater, take heart, you’re not alone. In fact, there’s growing cultural momentum toward more intentional connection. A recent Business Insider report found that while overall investment in social apps has slowed, investors are actively backing platforms designed to foster depth and combat superficial swiping. That includes tools that promote in-person connection, apps that emphasize shared values over appearances, and technology that supports long-term compatibility over short-term chemistry.

Kind Closings: When Values Don’t Align

Not every conversation leads to a long-term relationship. But if you’ve shared with kindness, and listened with dignity, it’s still a win.

Here's a gentle way to close things if you realize your paths are diverging: “I’ve loved getting to know you and I respect how thoughtfully you approach this. But after sharing what matters most to me, I’ve realized we’re heading in different directions. I really appreciate our time together, and I hope you find someone whose values match yours as beautifully as your intentions did with ours.”

This kind of ending honors both hearts and acknowledges that respect includes the courage to say ‘no’ gracefully when values just don’t align. It’s not rejection, it’s clarity. And clarity is a kindness, too.

Alison M. Cheperdak, J.D., is the founder of Elevate Etiquette, a consultancy where she teaches modern manners in a gracious and grounded way. She is the author of a forthcoming book, "Was It Something I Said? Everyday Etiquette to Avoid Awkward Moments in Relationships, Work, and Life."