6 First Date Conversation Starters That Will Build a Connection

6 First Date Conversation Starters That Will Build a Connection

First dates are a roller coaster of emotions. Because no matter how shy or bubbly you are, it’s easy to lose yourself in the emotions of the date prep. And when that happens, it’s natural to become tongue-tied and forget your conversation starters.

That said, while feeling this way is completely normal, there’s no denying it can seriously hinder your ability to connect with your date. While awkward silences are expected, missing out on potential love is the last thing you want.

The good news is that the days of suffering through awkward silences is no more. With these conversation starters and tips, you can take the pressure off yourself and ease into conversation naturally, so you don’t have to stress. Keep scrolling to learn more.


First Date Conversation Starters and Tips:

first date conversation starters

1. Start with small talk

It’s important to remember that your date is probably nervous, too. So while small talk is usually regarded as the most boring subject of all, it’s actually a perfect way to get the conversation going on a first date. Not only will this help you break the ice and get to know them a bit better, but it’ll also help you ease into deeper topics naturally because you’ll both be more comfortable and relaxed.

Small talk ideas for a first date:

  • How long did it take you to get here?
  • Are you from around here?
  • Have you always lived in the area?
  • How has your day been?
  • Have you been here before?
  • Do you enjoy this weather?

2. Get to know them

Once you’ve both had time to relax and chat with some small talk, you can try to get to know them a little better. While asking them questions is key here, this shouldn’t feel like a job interview. And neither of you should reveal everything about yourselves on a first date because you want to leave something else to uncover on a second date.

Instead, keep your questions light. Talking about your hobbies and what you like to do in your free time is a great way to get to know someone. Likewise, discussing movies, books, and TV shows also works well. Discussing these kinds of things will let you go beyond small talk and learn more about each other.

Additionally, if something comes up that you can both bond over—like a mutual hobby or shared love for a certain band or show—be sure to expand on that topic. Asking follow up questions is always a good idea, but sharing nostalgic memories (like the first time you watched that show) is even better. Having something to bond over will make it easier to connect.

Questions to ask to get to know someone on a first date:

  • Is there anything you’re reading or watching right now?
  • Do you like to travel?
  • What’s your favorite place you’ve visited?
  • What’s your dream vacation?
  • When’s your birthday?
  • Do you know your big three in astrology?
  • What’s your favorite season?
  • Do you have a favorite restaurant?
  • What’s your favorite food? Go-to meal?
  • Is there anything you like to do for fun?
  • Do you have any hobbies or passions?
  • What do you like to do in your free time?
  • What’s your favorite holiday?

3. Talk about work

Although keeping your work life separate from your personal one is a great boundary to have, there’s a strong chance work will come up at some point on a first date. It’s only natural, especially when you’re getting to know someone. For this reason, don’t shy away from discussing what either of you do, even if you’re in between jobs or what you’re doing now isn’t permanent. Honesty is always a good policy.

Work conversation starters:

  • What do you do for a living?
  • How did you get into your line of work?
  • Are you happy with your job?
  • What excites you most about your job?
  • What does a normal workday look like for you?

4. Play “this or that”

Playing “this or that” is a fun, engaging way to learn more about your date. So, ask them rapid-fire questions with two answers they have to choose between, and then have them do the same to you. Get creative with it! The more creative the questions, the more you’ll learn.

“This or That” conversation starters:

  • Ocean or pool?
  • Cat or dog?
  • Morning or night?
  • Salty or sweet?
  • City or country?
  • TV show or movie?
  • Vacation or staycation?
  • Cook or clean?
  • Fame or money?
  • Camping or glamping?
  • Hot or cold?
  • Summer or winter?
  • Spring or fall?

5. Delicately discuss childhood

While refraining from discussing childhood trauma or bad memories is a good idea on a first date, you don’t have to shy away from it completely. Instead, broach the topic of childhood delicately. In essence, this means asking surface-level questions, like how many siblings they have or whether they played sports as a kid.

Since childhood can be a sensitive subject, pay attention to how your date responds. If their body language changes and they seem more tense during this conversation, transition to another topic. Likewise, if they give you short answers, use your judgment to determine whether you should change the subject. It’s always better to err on the side of caution during a first date, and you can learn more about their backstory in time if you decide to pursue a relationship with them.

Childhood conversation starters:

  • Do you have any siblings?
  • Are you close with anyone from your family?
  • Did you vacation anywhere as a kid?
  • How did you spend your childhood summers?
  • Do you have a favorite childhood memory?
  • Did you play any sports as a kid?

6. Talk about the food and drinks

And last but not least: food and drinks. While this may sound like it should fit firmly in the small talk category, it’s actually one of the best universal conversation starters around because it’s not an emotionally charged subject. Besides, who doesn’t love food or a good drink? Plus, this is a great topic to use when you want to either extend or end the evening, or hint that you’d like you to schedule a second date.

Food and drink conversation starters:

  • What’s your favorite food?
  • Do you have a favorite cocktail?
  • Do you have a favorite restaurant?
  • What’s your favorite dessert?

Conversation starters to extend the evening:

  • Do you want to see a dessert menu?
  • Shall we get a nightcap?
  • There’s a cool bar around the corner. Want to finish up here and check it out?

Conversation starters to end the date:

  • I have to let my dog out when I get home, so I should probably be heading back soon; mind if I get the rest of this to-go?
  • I’d love to have another drink, but I have an early start tomorrow. Do you mind if we get the check?

Conversation starters to schedule a second date:

  • I have some free time this weekend and would love to check out a new restaurant. Do you have any recommendations?
  • I had a lot of fun tonight, and everything was great. Would you be open to seeing each other again?
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12 Comments

  1. Charlie-Elizabeth Nadeau
    July 25, 2022 / 2:26 pm

    This is great! I have to get back into the dating world soon, been putting it off. It can be so hard to meet people and go through that award first few meetings. These conversation starters are really helpful! Thank you.

    • July 26, 2022 / 1:29 pm

      It’s definitely intimidating getting back out there and navigating the waters! So, so glad you found this article helpful! Thanks for reading!

  2. July 25, 2022 / 3:10 pm

    Such great suggestions! I feel people always assume that conversation should just flow naturally if a date is going well. But that’s not always the case! It’s a great idea to have some of these starters in your back pocket to keep having fun and getting to know each other. Thanks for sharing!

    • July 26, 2022 / 1:30 pm

      Thank you so much! You’re so right—it’s easy to forget that some people are more shy than others and take more time to open up or have someone help coax them out of their shell. Thank you for reading!

  3. July 25, 2022 / 4:20 pm

    This is a fun post! I love the “get to know them” questions!

    • July 26, 2022 / 1:31 pm

      Thank you so much! Having fun is key to enjoying dating! Thanks for reading!

  4. July 25, 2022 / 4:42 pm

    You can’t go wrong with a handy cheat sheet like this. Nice read.

  5. July 25, 2022 / 11:24 pm

    Dating is different across cultures and ethnicity. The way people date, especially today, has changed over the years. However, these are some good conversation starters for a first date. The “This or That” game looks like a good way to know one’s date. Thanks for sharing Flawlessworld.

    • July 26, 2022 / 1:33 pm

      Very true, and very good point! The “This or That” is one of my personal favorites since it’s light and playful yet very insightful. Thanks for reading!

    • July 28, 2022 / 4:46 pm

      So happy to hear that! Thanks for reading!

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