10 Conversation ideas for a first date


Last Updated: March 12, 2024

Dating Tips

One of the most anxiety-inducing things about dating is knowing what to talk about on a first date. How can you make the right impression that leaves them wanting more? Which questions will give you the best idea of the person sitting across from you?

Relax! There are all sorts of great sugar date ideas, and we’ve got you covered with these 10 conversation starters for your first date.

First of all, don’t underestimate the power of small talk

We all moan and groan about small talk, but there is a reason it exists! Small talk allows us to splash around in the shallow end of the pool for a while until we feel comfortable enough to venture in further. So, don’t shy away from it!

Here are a few small talk topics that can help break the ice:

  • Show gratitude for organizing the date. One sure way to start off on the right note in your conversation with a sugar daddy is by showing appreciation. Thank them for meeting with you and express that you’re excited to get to know them.
  • Ask them why they chose this location, or share why you picked this place. Starting off the conversation by acknowledging where you are is a great way to ground you in the present moment. Point out something that you like about the cafe, restaurant or neighborhood.
  • Compliment them on their outfit. Genuine compliments can instantly put someone at ease. And, if they offer a compliment in return, accept it! Instantly rejecting someone’s praise can make the interaction awkward.
  • Ask them what their commute was like. Okay, okay, transportation talk can be a bit boring. And if that’s the case, you can move on from this topic quickly. But, maybe they saw something interesting on the way over. Or, maybe they used their commute time to read a book they’ve been obsessing over.

Ask them about their drink order


If you’re having a first date at a bar or restaurant, one of the first things you’ll learn about your date is their drink preference. This can be a great conversation starter!

If you’ve already sensed some playfulness between the two of you, you might even offer to guess their drink order before they make it. Be ready to explain your answer. For instance, you might guess wine if their profile pictures were taken at a winery.

Ask them about their work

This conversation is likely to come up on every first date you’ll ever go on. Since most of us work, it makes sense that it would be the first idea of what to talk about on a first date. But, it doesn’t have to be tired and predictable.

Go beyond the basic questions like, “So, what do you do?” with alternatives like:

  • What’s your favorite thing about your workplace?
  • Do you have something on your desk that’s important to you?
  • Do you have a coworker that you look up to?
  • If you were to quit tomorrow, what would you want to do instead?
  • What would the 10-year-old version of you think about what you do for work now?
  • If you could be the boss for a month, what would you change?
  • What’s something people assume you do as part of your job that is totally wrong?

These kinds of questions are a lot more open-ended and interesting than your typical career talk.

Segue into talking about their leisure time

Once the work conversation has run its course, you’re in a good position to talk about what they do when they’re not working. Again, you’ll want to avoid the typical questions like, “So what do you do for fun,” and approach the subject from a more thoughtful angle. Try these:

  • When are you at your most relaxed?
  • When life gets busy, what is one activity that you absolutely have to make time for?
  • What’s one self-care activity that you’re embarrassed to admit you like? When asking a man this question, you might get fun answers like getting a facial or singing in the shower. And when asking a woman, this might be when she reveals that she’s a huge reality tv fan. This conversation topic generally leads to some surprising reveals!
  • What’s a hobby or skill that you would learn if you had all the time in the world?

By approaching leisure time from these perspectives, you’ll inevitably open up the conversation to their current hobbies, favorite activities, friendships, and whether they have pets.

What’s your favorite thing about your hometown?

We all have a special connection with the place or places we grew up. So if you’re looking for what to talk about on a first date that will invite deeper conversation, this is a great one.

Ask them about what they like about their hometown. Or, if you were to visit it for the first time, what would they recommend you do? Are there things that only the locals know about?

This can also lead to conversations about how often they visit their hometown. Do they still have family or friends that live there?

If they’re still living in their hometown, ask them how it’s changed over the years. What are some businesses that they wish still existed? What are some changes they would like to see in the future?

Do you have any hidden talents?

If there’s one thing that every person has, it’s a hidden talent. Some people have good reflexes. Others are skilled at remembering names. No matter how quirky or inconsequential, everyone has something that they’re good at.

What’s nice about this conversation is that it invites your date to talk about themselves beyond the standard first date speil. Instead of feeling pressured to “sell themselves,” you’re encouraging them to reveal their authentic self. Plus, everyone likes to be acknowledged for their achievements, no matter how small.

If you could plan your own all-expenses-paid vacation, what would it look like?

If you like to travel yourself, this conversation is a good way to gauge compatibility. Is your date more interested in a luxurious trip to Dubai? Or are they content with fixing up an old van and traveling around the country? Do they like to travel with set plans or do they enjoy more of a “go with the flow” style? How about food? Are they adventurous with their palette? Or do they like the comforts of home?

Make sure to give them plenty of space to describe their ideal vacation. You never know. If things go well, you might be planning their perfect trip as a surprise in the future.

What is your favorite thing about dating?

These days, dating can feel like a slog. Between swiping and instant messaging and going on first dates, it’s easy to lose the fun.

But, there is a reason why we all do it! Some people enjoy the thrill of meeting new people. Others are drawn by the idea of finding their forever person. And there’s also something fun about having an excuse to try that new restaurant or wear a new outfit.

Of course, if your date is completely jaded with the whole process, this could be a potential red flag. Surely, there must be something they like, otherwise, they wouldn’t be sitting across the table from you. If not, you might wonder whether they’re this negative in other aspects of their life as well. It’s also not a good sign if this question unleashes a flood of complaints about previous dates and exes.

On the other hand, you could turn it into an opportunity for some light mutual complaining. Acknowledge that dating can be a real downer and then move on to another subject. You don’t want to dwell in negativity too long, but laughing about how terrible dating can be could ease the tension a bit.

What do people sometimes get wrong about you?

If you’re looking for what to talk about on a first date that invites a bit of vulnerability, this is a great question. After all, most of us are misunderstood from time to time. Maybe people assume you are a dog person when you actually prefer cats. Or perhaps people consider you to be shy when really you enjoy observing and sharing thoughtfully.

Remember that the way you frame the question can be lighthearted. But, don’t be surprised if your date takes the opportunity to get real with you.

If you could snap your fingers and make it so, what new habit would you introduce in your life?

We all know that if we just had a few more hours in the day, we would go to the gym more. Or, if we could find the motivation, we’d wake up twenty minutes early to meditate. But in real life, forming new habits is hard!

What we like about this conversation is that it will give you an idea of your date’s ambitions. Do they want to write a novel? Become more zen? Be more active?

If, on the other hand, they can’t think of anything they would change about their lifestyle or themselves, that might give you pause. Is it that they’re already working on building the kinds of habits they want to form? Or are they stuck in their comfort zone and unwilling to change?

Other advice for what to talk about on a first date


With these 10 topics, you’re sure to fill the evening with interesting conversation. If you’re still feeling nervous about what to talk about, consider these expert dating tips:

  • Start off on the right foot. Showing up to your date a few minutes early or on time can prevent you from feeling rushed and frazzled when you get there. If you will be late, send a quick message to your date.
  • Limit distractions. When things get awkward, many of us automatically reach for our phones. Try not to do this! It’s much easier to steer the conversation back into a good place when there’s not a screen getting in the way.
  • Hone your listening skills. Being a good listener isn’t something that comes naturally to everyone. That’s okay! You can learn to listen better by staying present in the conversation, using welcoming body language, and summarizing what your date has said. It may feel a bit strange at first, but these skills will become much easier over time. And your date will appreciate your effort.
  • Ask follow-up questions. Many of us have a habit of following up a date’s story with one of our own. And there’s nothing necessarily wrong with this. Both people should feel comfortable sharing about themselves. But, if you really want to make them feel special, stick with what they’re saying for a while. Ask follow-up questions or ask them to elaborate. This will show them that you’re genuinely interested in them.
  • Don’t put so much pressure on the first date. The fact is, first dates can be nerve-wracking. It’s not reasonable to assume that you’ll have perfect chemistry right out of the gate. And, a few awkward moments don’t have to mean that your relationship is doomed. If you enjoyed some parts of the night, give it another chance! Expressing your desires to a sugar daddy is not necessary on the first date unless the sugar daddy brings it up first or you feel the timing is right. First dates really are just practice runs. So, stay relaxed and lower the stakes in your mind a little bit.

Now you know what to talk about on a first date!

Once you try out a few of these creative ideas about what to talk about on a first date, you’ll feel much more at ease! Don’t be afraid to get creative, don’t overthink it, and be yourself. You’re going to do great!