On a first date, you have one job: get to know each other. After you’ve covered the basics — jobs, siblings, neighborhoods — you might want to dive a little deeper. Unfortunately, launching a full-blown investigation is typically frowned upon. (“What was your favorite thing about your ex? What are your biggest fears? By the way, I’ve always wanted to plant hydrangeas outside my house someday — what do you think? Oh, you’re allergic?”) So, how do you scope out who this person really is?
And if things do go well with your floral-averse love interest, your relationship might go swimmingly until it hits a roadblock. Maybe you realize you’re actually on different pages about saving versus spending, or clash over the religious traditions you want to pass down to your future kids. How well do you actually know each other?
A new book aims to deepen your understanding of your date or partner, regardless of how long you’ve known each other. Romance and Practicalities (out now) by Lindsay Jill Roth is a guide to sparking meaningful conversations with your date and partner. It’s inspired by the author’s own road to finding love.
She spent most of her 20s single, punctuated by romantic stints that lacked authentic connection and quickly fizzled. “I was losing myself,” says the writer and TV producer. “I found myself answering their questions the way I thought they wanted to hear.”
That changed at 31, when mutual friends set her up with a man she refers to as “The Brit.” Despite the long distance, they fell for each other over FaceTime. Behind a screen, Roth finally felt like she could open up. “It really allowed me to feel myself, put all the other crap aside, and say, ‘Who am I? What am I looking for?’”
To write Romance and Practicalities, Roth gathered insights from relationship experts, therapists, and more. The heart of the book is a list of 250 questions that readers can use to deepen their relationships and ensure they’re aligned with their partner on important issues.
“I wrote this book not because I was standing on a mountaintop preaching about healthy love,” she says. “I came up with a tool that I really needed and wish I had when I was single.”
Below, Roth suggests some questions that can reveal a surprising amount about your date, your partner, and even yourself.
Questions To Ask On Dates
These might seem surface-level, but you can learn a lot.
“Did you have pets growing up?”
You know what’s terrifying to hear on a first date? “Tell me about your childhood.” Even if you had a harmonious upbringing, you still feel transported to a therapist’s couch. Enter: a sneaky way to get the same kind of info.
“Talking about animals can open people up to talking about their childhood, a funny story, or why they’re afraid of something,” Roth says. Maybe their feline-loving dad adopted a hairless cat named Wrinkles to accommodate his new girlfriend’s allergy. Maybe they hate snakes because their brother used their slimy pet to play pranks.
“What’s on your bucket list?”
You don’t need to share all the same interests and goals, but, Roth says, “You’re looking to see if you can tick things off together in the future.”
If they’re dying to move abroad and you’d never miss your family’s weekly Sunday dinner, that’s good intel to have sooner rather than later. But if you discover a shared ambition to run a marathon, you’ve found a training buddy.
“What makes you feel better when you’re sick?”
This clues you in on how someone likes to be cared for, but it doesn’t have to come across as overbearing. For example, Roth suggests, “It’s winter and you show up at the bar. You’re taking your hat off and you say, ‘It feels like everyone is sick right now. When I’m sick, I just like to stay in bed and listen to music. What about you?’”
Five dates in, when they catch a cold, you’ll know whether to drop off chicken soup or simply not bother them.
“If we were stuck on a desert island, what skills do you have to keep us alive?”
Not things — skills. Then ask follow-ups. “You can catch that many fish? Why?” It’ll uncover stories from their Boy Scout days or their annual lake trip with their high school friends.
Questions To Ask Your New Partner
So your trout champion reeled you in, and now you’re official. Congratulations!
Keep the curiosity going. The right person won’t feel grilled. “When you find someone who’s willing to answer questions and get a little bit deeper, that’s a great sign,” Roth says.
That’s not the only perk. “It sounds crazy, but I hear over and over that couples are three, four, five questions in, and they’re putting the book down and having sex. They’re not even going up to the bedroom because it’s that intimate,” she says.
“What does that mean to you?”
If a topic is deal-breaker-level important to you, get specific, even if you think you’re both on the same page. For example, Roth says, “If you’re a spiritual person and want someone who’s spiritual too, does that mean practicing yoga? Saying a prayer before you go to bed? Having crystals on your nightstand?”
Ask sooner rather than later. Otherwise, you might find yourself falling for someone who doesn’t actually fit what you’re seeking.
“How do you fight?”
To keep your clashes healthy, get this one out of the way early on. Roth learned this during one of her first arguments with “The Brit” (now her husband). “We got into bed that night, and I wanted to keep talking about it, and he needed to process it. He turned over, facing away from me, and didn’t realize that that gesture would physically make me feel hurt,” she recalls.
Once they made up, they figured out a solution: He’ll let her vent, then she’ll give him space. Whatever your answer is, it’ll let you fight about the actual issue, not how you’re acting during the disagreement.
Questions To Ask In A Long-Term Relationship
Make sure to cover these subjects before you make a commitment like moving in together or getting engaged.
“Why don’t we argue?”
It might sound counterintuitive, but if your relationship is hunky-dory perfection 24/7, you could actually have trouble communicating.
“Are you holding something in? Is there something you don’t feel totally comfortable sharing? Do you need to work on that?” Roth asks.
When it comes to finances…
“The most important question is not how much money they make,” Roth says. It’s their philosophy. Try:
- When you were growing up, how was money talked about in your home?
- Do you have student loans?
- Do you have debt or owe money to anyone?
- Do you pay your credit card bills on time? In full?
- Do your parents pay your phone bill?
- On vacation, would you rather splurge on a nice dinner or a boat ride?
Since money touches every aspect of our lives, these conversations should happen early and often. It’s a sensitive subject for many people, but you can ease into it by opening up first. “Start with, ‘I was always taught that you should pay your bills in full every month,’” Roth says. (Or whatever’s true for you.) “What about you?”
How To Talk About The Tough Stuff
Get it out of the way. Per Roth, “The sooner you talk about things, the easier it is to revisit something in the future.”
Pick a low-pressure location. “If you’re talking about sex, I don’t recommend you do it in bed.”
Avoid the phrase, “We have to talk.” “When you hear those words, you start freaking out.”
Establish your intentions. “Start with, ‘I want to bring up something that’s important to me. I’m open to listening to your feelings, and if I say something that makes you feel upset or defensive, this is all coming from a good place.’”
Don’t avoid the scary subjects. “Set it up so your partner knows that it takes courage to do what you’re doing and be kind. Say, ‘There are a few things I’m nervous to talk about. Can we set a time aside to have a conversation about what’s been on my mind?’”
If you’re afraid to bring something up, blame Roth. “Say, ‘I read this book. Is it OK if we go through a series of questions to make sure we’re covering all our bases?’”
When you dig deep, you can strengthen your relationship — or realize it’s time to walk away. “You don’t always need to have the answers, but you need to commit to finding them together,” Roth says.
