There is nothing worse than first-date silence. In fact, a singular fear of it kept me from dating for years.
The onset of this fear was the result of a particularly cringe-worthy date: After seeing “27 Dresses” (bad start, I know), my date and I strolled to the nearest Starbucks to get to know each other better. But that’s not what happened.
Instead, she sat silently. She was timid and shy. Feeling pressure to fill the deafening void, I settled on illuminating topics like the temperature of my coffee, my past traumas, and the headlines on nearby magazines. Nothing worked.
The date was essentially an 80-minute monologue by yours truly. By the end of my set, I felt uncomfortable and raw, like I’d just been through an intense therapy session. Needless to say, we never went on a second date.
To protect you from what she and I experienced, consult this handy guide for engaging conversation-starters that’ll fill the silence, help you learn more about each other, and spare you from examining extraneous topics like why you wanted to go to art school but settled on community college instead.
1. What kind of person are you looking for?
“This question, while maybe obvious to some, will give insight into your date’s personal values, lifestyle, passions, and dating intentions,” Deanna Cobden, dating and relationship coach at Dateworks, says. “It also gives you a chance to be upfront about the kind of person you’re looking for.”
2. What are you obsessed with these days?
“A lot of people get asked about their passions in life, but identifying what is capturing their attention at the moment makes them reflect in a completely different way,” Claire AH, dating coach and owner of Friend of a Friend Matchmaking, says. “It’s a snapshot of what’s important to them that leads to more conversation.”
3. If you could have lunch with any celebrity in history who would it be?
Will they choose a former political leader? An Oscar winner? A Kardashian? The possibilities are endless and the answer can reveal plenty about their values, interests, and taste level.
4. How do you spend your weekends?
“This will tell you a lot about the person’s, habits, hobbies, likes, dislikes, level of physical activity, and the types of relationships that they have in their lives,” Cobden says.
5. Are you a morning person or a night owl?
Will you two spend your mornings at brunch or sleeping off the late-night dance party?
6. Who has been the most influential person in your life?
“This will give insight into what and who they value, as well as their family life as far as relationship dynamics are concerned,” Cobden says. “It could also be a window into their long-term goals and any plans for family and career.”
7. What is your sign/Myers-Briggs type?
If your date is into astrology or personality testing, you won’t talk about anything else for at least 30 minutes.
8. What’s something you’re looking forward to in the near future?
“This will give you a broader understanding of their hobbies, goals, and lifestyle,” Cobden says. “It’s a nice way to connect over something exciting coming up for them and also share something exciting that’s in store for you.”
9. What’s something you’ve always wanted to do but haven’t?
It’s a question with potential for an exciting answer and — bonus! — can give you an idea for a more thoughtful second date, presuming things go well.
10. What does a typical day look like for you?
“Find out more about their day-to-day lifestyle,” says Cobden. “It gives them the freedom to share more than a one-note answer, unlike ‘what do you do for work?’ or ‘how do you spend your free time?’”
11. What’s your dream job?
The question could reveal a passion or talent you might not know about and perhaps share.
12. What’s your favorite hidden gem in the area?
“This question leads you off the beaten path and will give you insight into what they value about their surroundings,” AH says. “Ask why they like it, and maybe you’ll end up there on a future date.”
13. If you won the lottery, what’s the first thing you would buy?
Will they set their parents up for life? Invest? Blow it all on frivolous things? Their answer is telling.
14. Do you have any passion projects?
“You’re not asking about work and you’re not asking about their side hustle, which people tend to value more,” AH says. “The question will let you know what gets them excited and [provide] a deeper dive into their personal and/or professional interests.”
15. Who are you embarrassed to admit you follow on Instagram?
We all follow somebody we aren’t proud of, so find out who their guilty pleasure is. The question is cute, fun, and good for a chuckle. Just be prepared to answer, too.
16. Do you think a younger version of you would be surprised by who you are now?
“This lets you in on the person your date was when they were younger and encourages introspection on how they got to where they are now,” AH says. But be forewarned: “There’s a little danger of this getting heavy.”
17. What would you do with your extra time if you never had to sleep?
It’s a fun hypothetical question that they’ve probably never considered before.
18. What’s something I’d be surprised to know about you?
“This is an interesting question that gives your date a chance to share something about themselves that they might not otherwise think of,” Cobden says.
19. Who is your favorite YouTuber?
Do they like mukbangs, ASMR, or makeup tutorials? It’s a question that can lead to topics as vast and expansive as YouTube itself.
20. Keep the conversation going.
Being a good conversationalist requires being a good listener. “Active listening means making eye contact, nodding, and attending to whomever you are talking rather than paying attention to your phone or any other distraction,” says Stacy Hubbard, LMFT and certified Gottman therapist and master trainer. Good posture and paraphrasing the other person’s responses to your questions are other ways to show you’re actively listening.
When asking these questions, do so in a light, conversational tone. If you don’t and fire them off in quick succession, your date risks feeling like a job interview. So take your time and emotionally invest in the conversation. Expressing empathy validates your conversation partner.
“When all else fails, think: who, what, where, when or how,” Cobden says. “If there are a lot of lulls or if one or both of you is nervous, sometimes it’s not about firing another specific question at them. It’s often better to expand on what they’ve already shared.” When you get to the emotional reasons behind their answers, it not only keeps the conversation going, but it also creates a deeper connection than moving to the next question would.