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.
1. 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 yourselve.
These initial disclosures and early rapport-building will oil up the gears so that the following conversation will feel much easier and more natural.
2. Ask what their day or week has been like.
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.
- So, how has your day been?
- 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?
3. 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.”
4. 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.
5. 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 Muñoz, LPC, recently told mbg.
6. Compliment them—genuinely.
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,” Muñoz recommends.
7. 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 enjoy what you do? What do you like/not like about it?
- 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?
8. 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.