By Kelly Gonsalves
Contributing Sex & Relationships Editor
Kelly Gonsalves is a sex educator, relationship coach, and journalist. She received her journalism degree from Northwestern University, and her writings on sex, relationships, identity, and wellness have appeared at The Cut, Vice, Teen Vogue, Cosmopolitan, and elsewhere.
Good conversation on a first date can sometimes be elusive. In many cases, you’re talking to a total stranger that you know virtually nothing about, yet also kind of want to impress, while also sort of trying to evaluate compatibility. There’s a lot happening at once!
To help keep the conversation flowing, here are a few ideas for what to talk about during this first encounter.
Things to talk about on a first date.
Start with casual, contextual conversation.
Don’t feel like you have to jump right into an inquisition as soon as a first date starts. The deeper conversations will come more naturally once you’ve established a bit of a foundational rapport between you.
When you first arrive on the date, try starting with a little bit of casual conversation drawing from the context you’re in. For example, if your date picked the restaurant you’re at, ask her if she’s been here before, how she discovered the place, and what she likes about it. Or if you’re at a bar that specializes in quirky cocktails, ask him questions about his go-to drink and share your own. You could also talk about the part of town you’re in and how much time you each have spent in the area, an interesting article of clothing or jewelry your date has on, or where they came from prior to meeting up with you.
From there, let the conversation flow naturally–maybe they’ll bring up how hard it is to find good Thai places in the city you’re in, or a good friend who brought them to this spot before, or how much they love eating outdoors. Pay attention to what comes up, ask follow-up questions, and offer up your own thoughts or stories that relate back to what your date just shared.
Some people refer to this category of conversation as “small talk,” but the key to making it feel vibrant and interesting is actually engaging with what the other person is sharing and leaning into any opportunities for you both to start disclosing unique details about yourselves. These initial disclosures and early rapport-building will oil up the gears so that the following conversation will feel much easier and more natural.
Ask what their day or week has been like.
Great relationships start with great sleep.*
This might seem like a boilerplate question, but don’t let it be. Think of this question as a way of tapping into what’s actually top of mind for this person right now. When people talk about how their day or week is going, they’ll usually reveal a little bit about what’s spinning their wheels at present–what problems they’re currently having, what dreams they’re currently chasing, or what pleasures are currently lighting them up.
One of the reasons first dates can feel so awkward is that the conversation can sometimes feel like an interview, with each person taking turns asking the other the basic get-to-know-you questions. To open the door to true connection and get past the canned responses, it helps to try to learn about their world as they’re experiencing it presently. Asking about what’s going on in their life currently is a great way to tap into that.
However they respond, even if it’s just an exasperated sigh and brief comment about how stressful work is, ask a follow-up question that lets them know that you actually want to hear more about it.
Follow-up: Oh, what’s been so stressful about it?
What have you been up to this week?
Follow-up: Wow, how was that experience for you?
Follow-up: That sounds like a lot. Is that a usual week for you?
Follow-up: It’s nice that you got to spend some time with your parents. Are you close with them?
Talk about what’s really happening in your world.
Likewise, bring up the things that are presently top of mind for you. Dating coach Clara Artschwager recommends bringing your full, messy, imperfect self into your dates. Don’t worry about trying to only show off your highlights and big accomplishments–be real about what life is actually like for you these days, both the good and the bad. People generally enjoy being around those who are willing to be open and vulnerable, Artschwager points out.
“When you meet someone, whether it’s in a romantic context or a work context or anything, and you feel how at ease they are with themselves, that makes you feel good. That makes you want to open up, whether you realize it or not,” she recently told mbg. “That’s when we’re like, this is a nice interaction. This is a nice conversation.”
Bring up something from their dating profile.
If you matched through a dating app, a person’s dating profile is an excellent place to look for first date conversation topics. Before you meet up, review their profile and try to find something you can bring up when you’re together. Not only does this show you were really paying attention to the details they chose to share, but what a person puts in their profile can again give you a clue into what they’re thinking about presently.
Notice and ask about the small details.
Practice active listening as they talk: Really focus on trying to understand what they’re saying and feeling, rather than trying to think about how you’re going to respond when they stop talking. Then, comment on and validate the things that you’re hearing and noticing about them.
“People generally open up more when they’re being seen, heard, noticed, and listened to in the little details of who they are and how they express themselves,” couples’ therapist Alicia Mu?oz, LPC, recently told mbg.
Another way to show that you’re really paying attention to your partner is by complimenting them–and not just on their looks. A little playful flirting can be fun, but in addition to that, see if you can find ways to compliment your date’s personality or energy. After you’ve been talking for a little bit, see what little things you notice that you really like about being around this person.
“Notice someone’s jewelry, the logo on their T-shirt, their overall energy level, their sense of humor, their way of expressing themselves, and celebrate that,” Mu?oz recommends.
Ask how they feel about their job.
Their job will probably come up organically at some point in the conversation. But beyond just learning what they do for work, ask them how they feel about it–you’ll likely get a much more interesting, genuine response.
“It’s boilerplate to talk about work, so if you’re going to go there, you might as well take it a step further,” relationship coach Julie Nguyen tells mbg. “What excites them about their job? What doesn’t excite them about their career? What are their dreams for the future? What did they want to be as a kid? By approaching them with curiosity, you can transform simple questions into deep discussions where you draw out the essence of who they are as a person instead of a rehearsed answer.”
Do you like working with your team/boss/clients?
How did you get into that line of work?
Have you always wanted to do this type of work?
What do you see yourself doing in the future?
If you could have any job in the world, what would you choose?
If money weren’t an issue, how would you be spending your days?
Ask what things they’re passionate about these days.
Talking about work won’t light everyone up, and people are so much more than their job titles. So, find ways to ask about all the other ways that people choose to spend their time. Specifically, asking what someone is passionate about or loving these days can open the door for them to share things that genuinely light them up: a new podcast they recently discovered and can’t stop listening to, their fascination with astrology and crystals, or a new creative endeavor they’ve started exploring on the weekends.
Ask how the last few years have impacted them.
When you feel like you’ve built up enough conversational trust between you two, you can start to ask questions that get into the deeper stuff. For example, ask about how they’ve been doing in these last few years since COVID entered into our lives. Most people have been impacted at least to some extent, so you’re almost certain to get more personal through this question.
Be mindful entering this part of the conversation: You might end up talking about how isolation and Zoom fatigue have impacted your mental health, or you might end up in a politically-tinged conversation about how people have or haven’t responded to living through a pandemic. If it ends up being the latter, don’t worry–people sometimes feel like they need to avoid talking politics on a first date, but the truth is that it’s better to know sooner rather than later whether the two of you are aligned in terms of values and viewpoints. Any differences that come up may or may not be a dealbreaker for each of you, but either way, those are important details to know about someone you’re considering dating.
Learn about their family life.
Speaking of going deeper, asking about your date’s family can be a way to peel back the layers and get to know more about their background and why they are the way they are.
What’s your relationship like with your parents?
Do you have any siblings? Are you the oldest/young/middle child?
What was your childhood like?
Did you like the place where you grew up?
Ask what they’re looking for from dating right now.
Last but not least, if you’re on a date, it only makes logical sense to ask about each other’s dating goals and intentions. You want to make sure you’re on the same page about what you’re both looking for, whether that’s something casual, something serious, or some other type of relationship.
What brings you to the dating apps?
Are you a relationship person?
I usually like to take things slow while getting to know someone. How about you?
What not to talk about.
“On a first date, I don’t consider really anything off-topic to talk about,” says Nguyen.
Although common wisdom holds that you should never talk politics or religion on a first date, the days of trying to politely paper over differences for a date are behind us. A 2021 study by the dating app Bumble found that 62% of adults believe it’s important to talk about key social issues on a first date, including topics like gender equality, race, the environment, and more, and 75% said they’d only date someone if most of their political and social views aligned.
The truth is, if you’re looking for a long-term partner, shared values are going to be an important bedrock for your relationship–so the sooner you can learn where a potential partner stands on the issues that matter to you, the better. That isn’t to say that you should spend a first date grilling each other about their stances on every political topic, but don’t feel the need to beat around the bush when it comes to your values either.
That said, there are a few things you may want to avoid talking about on a first date, such as:
Your highlight reel: Likewise, be mindful of the amount of time you’re spending talking about yourself, your accomplishments, your travels, and all the other things that you think make you great. Remember, this isn’t an interview. As Artschwager points out, the point here isn’t to show only the best parts of you but rather to let this person see your whole, authentic self–flaws, doubts, demons, and all.
Heated feelings about your ex: Sometimes it can be appropriate to discuss past experiences with dating and relationships on a first date, Nguyen notes. Just be mindful of spending too much time rehashing the details of specific relationships, especially if you’re fresh off a breakup; your inability to stop talking about your ex may signal to your date that you haven’t moved on yet. Trash-talking your ex can also be a red flag for many.
How badly you want a relationship: While you should definitely be clear about what you’re looking for from dating, it’s also important to recognize when you’re coming into dating from a place of scarcity. For one thing, most of us don’t often get enthused by meeting a total stranger who already has a ton of expectations of us and how much we’re expected to add to their life. Not only can that create a lot of pressure on your date, but it can also eat away at attraction. We tend to be much more drawn to people who seem to already have a full life and who themselves have lots to offer those around them, rather than those who have a lot they’re asking for.
How to keep the conversation going.
There are a few ways to avoid awkward silences:
Ask thoughtful follow-up questions.
When your date tells you something, validate what they said (“that’s cool!”) and then ask another question based on what they just said (“Have you always been so ambitious?”).
Don’t jump from topic to topic too quickly.
Take your time with each topic, really trying to color in a full picture of this part of your date’s life or mind and leaving space for your date to share as much as they want about the current topic. Just as well, make sure you’re also taking time to share your thoughts or stories related to the topic, so they’re getting just as full a picture of you.
Name the awkwardness.
The truth is, awkward silences happen. Sometimes your mind just goes blank, and you can’t think of what to say next. It’s OK to let them know you’re blanking, or call attention to the fact that first dates can be awkward. You can even poke a little humor at the whole situation, if that’s your thing. Sometimes naming the discomfort and sharing a laugh about it is all you need to diffuse the tension and turn it into a connective moment.
Enjoy the silence.
Silence doesn’t always have to be a bad thing. If you find yourself at a natural lull in the conversation, it’s OK to sit back and take a beat. Check in with your surroundings. What interesting things are happening in the space around you? As you observe, you can still emote–a smile and a pleased “mmm” sound, for example, let your date know that the silence isn’t bothering you, and you’re still enjoying the experience you’re having together. You can even tell them that directly, or comment on what you’re taking in from the environment. For example: “God, this breeze feels so good. I really enjoy afternoons like this.” Or, “Ooh, what do you think that couple over there is talking about?”
For the most part, you can really talk about anything you’re in the mood to talk about on a first date. As Nguyen points out, almost any topic is fair game for conversation as long as it’s approached thoughtfully. “What’s more interesting is navigating the tension of the date appropriately so you don’t share too little or too much,” she adds. “Having the right attitude and remembering to stay balanced with what you share invites intrigue to the date and enriches the interaction dramatically.”
Share the things that are exciting, important, and interesting to you, and ask questions to help your date do the same. And remember: Dates should be fun! Focus on enjoying yourself, authentically getting to know this person and allowing them to get to know you, and just having a fun, connective experience together.