7 Dating Questions to Ask the Next Time You Feel Like Giving Up

The modern dating pool can be a precarious space to navigate. Between ghosting, love bombing, endless dating apps, and catfishing, finding genuine connections when you’re single can feel impossible. But what if the right questions could cut through all the noise?

Brittany and Anthony Xavier, who have been married for nearly 12 years, are here to help if you’re ready to delete the apps for good. Their advice? Improve your odds by asking the right questions.

On The Long Game, they shared the exact questions they would ask each other if they were dating again—the conversation starters that helped them go from strangers to soulmates.

Whether you’re getting back out there or just want to date more intentionally, these seven questions can help you find real compatibility faster.

7 Smart Dating Questions to Ask Early In a Relationship

1. “What are your intentions?“

The Xaviers didn’t waste time on small talk during their first encounter. They met by chance at a restaurant while out with their separate groups of friends—two of whom happened to know each other.

Brittany was upfront within the first three minutes: She was a single mom to a three-year-old. “You asked me what I like to do for fun, and I said, ‘I am a mom of a three-year-old, so most of my time between work and school, I am with her,” Brittany recalls.

Anthony and Brittany ending up staying at the restaurant for hours after their friends left, just talking. The honesty had quickly opened the conversation to intentions. As Anthony explains, a single parent needs to know if you’re looking for marriage or just having fun. 

For Brittany, setting intentions early is a non-negotiable. “When I met Anthony, I knew I wanted to get married, and I wasn’t going to date someone just to have fun,” she explains. “Because I had Jade, I didn’t want to bring guys around just for fun, so I set standards in my head that if a guy didn’t connect with my daughter, I’d cut it off.”

2. “What do you like to do for fun?“

Brittany says classic icebreaker questions reveal more than you might think. You’re not just learning about the obvious, you’re also discovering whether your lives would naturally mesh and learning about their vibe.

Along with “What do you like to do for fun?” and “What do you do for work?” or “What do your weekends look like?” or “What is your family life like?” these questions help you understand someone’s priorities and how they spend their time.

“It helps you get an idea if he or she is someone who goes to parties, the museum, the park, or goes to exercise,” Anthony explains.

3. “Do you see kids in your future?“

Some conversations can’t wait until you’re deeper into the relationship. Your stance on children is one of them.

“If you are someone who wants to have kids and you are dating someone who doesn’t want kids, you should not settle and think you are going to change that person,” Brittany says. This isn’t about timing—it’s about fundamental compatibility. The truth is, you can’t change someone’s mind on major life decisions, so why waste months or years hoping they will? 

4. “What is your 5-year or 10-year plan?“

This question reveals work ethic, ambition, and whether someone thinks seriously about their future. Do they have dreams and goals? Are they actively taking steps to achieve this goal? Someone who is working toward personal goals demonstrates hard work and individual accountability, which are key indicators in the dating game. 

“Ask what your five-year plan is? What is your 10-year plan? What kind of job do you see yourself doing?” Anthony says. “These questions show their work ethic and whether they are a go-getter wanting to climb upward.”

5. “What’s something you’ve been into lately that most people wouldn’t guess about you?“

Brittany thinks this innocent question is actually a brilliant way to help you identify potential red flags. Do they have any questionable or slightly creepy hobbies that you wouldn’t want to share with mom? “If they say something really off-putting, it would be a vibe check,” Brittany explains. But it also reveals hidden depths and interests that might no come up in typical first-date conversations. Win-win.

6. “Is there a dream trip you haven’t taken?“

Travel compatibility matters more than you might think. This question will help you decipher if the person is a homebody or adventure-seeker, how they prioritize experiences, and their level of unhinged-ness. “Do they like to stay home, or do they have aspirations to go to Paris or Italy?” Anthony says. “This question helps you determine how spontaneous the other person is.”

7. “What is a small, everyday thing that makes you happy?“

This question might be the most telling of all. It helps you determine their perspective—are they a pessimist or do they have a positive outlook on life? Someone who can’t identify what brings them daily joy might not be ready for a relationship—and if they say they’re waiting for “the one” to bring them happiness, be sure to Amazon 1-Click them a copy of Melody Beattie’s Codependent No More.

“You can see if they are grateful for the little things and reflecting on life,” Anthony says. “If they don’t know what makes them happy, there might be something deeper to that. You can tell the person’s mindset.”

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