First Date Conversation Starters That Won’t Bore Them To Death

First Date Conversation Starters That Won’t Bore Them To Death

First dates can be awkward as the dickens, but with the right conversation starters, they don’t have to be! Here are some fun and simple ways to get your date chatting and get rid of those first-date jitters. 

1. Dive Into Passions

The ol’, “What do you do for fun?” has been done to death. However, you can still get to know someone through their hobbies by just expanding on the trope. Ask what they’re passionate about and why. Maybe it’s a sport or a skill of some kind, which bleeds into follow-up questions like how they first learned or what inspired them to do so.

Brooke-Cagle-Txsvqngnjq4-UnsplashPhoto by Brooke Cagle on Unsplash

2. Explore the Work Day

Asking people what they do for a living isn’t the conversation starter it once was. With the introduction of dating apps, that information is freely offered before you see them face-to-face. Instead, expand on it by saying something, “Take me through a typical work day for you.” 

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3. Get to Know Fido

Even if you’re both nervous wrecks, pet talk always eases people. It’s a good way to get them talking about someone they love, relieve any tension, and see some cute cat pics.

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4. What Tickles Their Funny Bone

A person’s sense of humor will tell you if you’re truly compatible. While it can be tough to gauge naturally, ask a simple question such as, “What’s the last thing you truly laughed about?” 

Giorgio-Trovato-6Rkkr2Fh2-I-UnsplashPhoto by Giorgio Trovato on Unsplash


5. Weekend Plans

Weekend plans give you great insight into a person’s hobbies and interests, so be sure to inquire. Their plans also lay the groundwork for dozens of follow-up questions, which keep the conversation flowing.

Rene-Ranisch-Lsmf7Gjodz4-UnsplashPhoto by René Ranisch on Unsplash

6. Favorite Food Spots

Ask where they like to eat in the area and why. If you’re interested in a second date with them, their answer tells you which places to avoid and which sound like the best options—and even if it’s not in the cards, you might just get a good reco out of it.

Jarritos-Mexican-Soda-Ie5Qlonrwiy-UnsplashPhoto by Jarritos Mexican Soda on Unsplash

7. Upcoming Travel Plans

Find out if they plan to travel anywhere. Where are they going and what inspired them to visit? Have they been before? Let them open up the world to you, and the conversation! 

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8. Pop Culture

There’s no shortage of pop culture themes to discuss. From TV shows and movies to books and video games, everyone indulges in one or more of them. It’s also an excellent way to spark an engaging conversation.

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9. Talent Show

Not an actual talent show, of course (unless your date seems into that). No, ask them about any weird talents they have! And if they haven’t any odd talents, it’s a perfect place to segue into which talents they wish they had and why.

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10. Go Down Memory Lane

Speak about their hometown or fun experiences they had as a child. Allow them the chance to walk you through milestones in their lives—you’ll learn a lot about them, too. 

Matt-W-Newman-Tlt9Imto3Vg-UnsplashPhoto by Matt W Newman on Unsplash


11. Be a Bookworm

Not everyone is a reader, but chances are you’ll know that about your date beforehand. If you’re both bookworms, ask them any number of things from their favorite author or book, right down to a book they wish they could read again for the first time.

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12. Ask for Recommendations

A good way to get people talking is by asking about their interests—a good way to get people excited is by asking them to share them with you. What are their favorite restaurants, shows, or movies? 

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13. Bucket Lists

Everyone has at least one thing they’d like to see or do in their life. Find out what your date’s bucket list is and listen intently so you can ask any follow-up questions. You never know, you may have similar wishes!

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14. Funny Hypotheticals

Hopefully your date has a sense of humor, and if they do, ask some funny hypothetical questions to get laughs in. What’s their favorite karaoke song? Did they give any funny nicknames to their pets? 

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15. Observe the Room

Sometimes the best conversation starters are right in front of you. If the discussion falls a bit flat, take a peep around the area and bring something to their attention. You might get their views on a topic or have a few laughs.

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16. The Rougher Stuff

It’s always awkward to talk about religion or politics on a first date, but in this day and age, people want to cut to the chase. If you want to inquire about potential red flags delicately, ask something like, “Did you grow up with religion?” or, “What party does your family support?” 

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17. Fun Quirks

We’ve all got our little quirks, whether we admit it or not! Open the stage for them to share theirs with you and see where the conversation takes you.

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18. Worst Opening Lines

Dating apps come with their own special brand of terrible pick-up lines. Speak with your date to see if they ever received one that really stuck out to them.

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19. Go-Tos

Does your date have a go-to coffee shop? That one movie they always watch when they’re sad? Learn more about them by asking what some of their go-tos are!

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20. Second Date Feelers

If you see a second date in the future, it’s time to ask some specific questions like if they have anything planned in the next few days or what their thoughts on sushi bars are!

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