couple laughing together having a conversation

The 20 Most Fun and Outrageous Conversation Starters for Any Couple

Stop us if you’ve heard this one before…

It’s Saturday night and you and your spouse decide to go out to dinner, but there’s nothing to talk about. You stick to the same “how was your day” routine and have what seems like the same conversations for the millionth time. You talk about the girl at work that stole your yogurt, what to get as a snack for the little one’s next soccer game, and of course, when your next grocery store escapade will be. Is there anything new to talk about?

Well have no fear, Crated with Love is here! We’ve put together 20 of the most outrageous and inconsequential conversation starters for your next night out! We guarantee you won’t have any of those “same ole” conversations with these questions!

Why did we create this post?

At Crated with Love, we believe in three things in marriage (well, we believe in a lot of things in regards to marriage but for the sake of this article we are sticking to these three): Communication is the key, discovery is the lock, and laughter is the peephole which all work together to open the door when an awesome date night comes a-knockin’!

We’ll explain a little more at the end of the list as to what that means and why we chose the questions we did, but let’s not wait any longer! Here are the 20 most outrageous conversation starters for any couple!

Want to connect and laugh more with your partner? Check out these conversation starters and date night games!


1. You have been chosen to live in space for 10 years. You are told that you can bring one movie, one book, and one lifetime supply of one specific type of food. What do you bring?

2. During a safari in the middle of the jungle, you are bitten by a poisonous millipede that gives you the ability to transform into any type of bug. What bug do you choose to turn into? Yes, you HAVE to answer!

3. While checking out a new home you’re thinking of moving into, you open a closet that magically teleports you to the Middle Ages. A wizard finds you and tells you that you must start your own shoppe in order to save up money to buy his teleportation serum to get back to your time. What is the name of ye old shoppe and what do you sell?

4. Pickles, tuna fish, or ghost peppers. You must add one of these on every dish for the rest of your life. Which one do you choose?

5. Your phone rings. You answer it. It’s the world book of records and they are dying for some new content. What one thing do you think you can do to get into the record book? What do you think your spouse could do?

6. You decide to visit Las Vegas. Unfortunately, a giant geo-electrical storm erupts with a mass amount of lightning. A bolt strikes the entire city, causing all the power to go out except the little karaoke joint you are currently in. It has been said that the sweet sound of the perfect karaoke song can cure and geo-electrical storm. What song do you sing to save the world?

7. You are a mad scientist that has the ability to combine animals. Using your relationship as inspiration, splice together 4 different types of animals. What animals do you choose and why do they resemble your relationship?

8. As a small hobby, you invent a super powerful underground drill that has the ability to dig a tunnel from your home to any place in the world. As its maiden voyage, you decide to dig to the one place on earth your partner has always wanted to go. Where do you dig to first?

9. A group of aliens invade your home and say that they’ll take you away unless you can provide them with the perfect meal consisting of two sides, and entrée, and a scrumptious dessert. What is the best meal you’d make for them? Would it save you?

10. While visiting the middle of the creepiest forest on Earth, you find yourself in a face to face battle with an evil witch. But this isn’t an ordinary run-of-the-mill witch. She can morph herself into you and your partner’s greatest fears. Her only weaknesses are scented candles. What does she turn herself into and what scent would you defeat her with?

11. Chocolate chip, banana, or blueberry. Which type of pancakes would you choose to eat for the rest of your life? Oh yeah, chocolate chips give you the ability of flight. Bananas give you the ability of super speed. Blueberry gives you the ability to read minds. Which power would you use most in your day to day life?

12. Which bear is best?

13. While rummaging through a yard sale, you come across a magic remote control that gives you the ability to insert yourself into any TV sitcom. Which show are you planting yourself into and which character would you replace?

14. What is the worst word in the world? What is the best word? What is the most medium word? If you could create a new word to describe your relationship, what would that word be and why?

15. In the newspaper (what’s that?), you find a coupon for the world’s best stylist. They are offering a complete wardrobe update and a new hairstyle for only $19.99! All you need to do is bring them a photo of the celebrity that best represents the new style you want. Whose photo do you bring?

16. On Amazon, you find a DIY bath bomb kit that will be delivered in the next 5 minutes if you order now. Get it! For your first bath bomb, you decide to create one that smells just like your first date. What would that bath bomb smell like?

17. Search “deep sea fish” into Google images. Which fish best represents your partner when they didn’t get enough sleep?

18. You are writing a new children’s book and are having a hard time coming up with a name. Create one by filling in the blanks: The [your partner’s best quality] [the animal that best personifies your partner’s love for you] and the [your partner’s favorite color] [the one type of food that your partner hates].

19. You just realized that you have an extra $200 million in the bank and decide to buy an island to create your own community. The island only has room for one shopping store, one restaurant, and one “owner’s choice” establishment. What three are you picking?

20. Steven Spielberg knocks on your door and tells you that he has completely run out of ideas for movies. He wants to make one about your relationship! Creating a movie plot (adding dramatization of course), who would play the main characters? Where does move first start? What would be the struggle or thing that needs to be accomplished? What would the climax be? What would be the resolution? Who is the villain?

Want to connect and laugh more with your partner? Check out these conversation starters and date night games!


There you have it! We weren’t kidding, pretty outrageous, huh? Believe it or not, every one of these topics has a purpose. Well, at least most of them do.

At the beginning of this article, we told you that communication, discovery, and laughter were three ingredients to a great date night.

With these conversation starters, our goal is to bring those things together. By having intense, thought-provoking conversations, you are not focusing on your phone or the television in the corner. You are focused on each other.

Yes, some of the topics may be a little out there, but they provide the opportunity for you to get to know your partner on a deeper level or to help you realize how much you know them already.

Laughter is such an important part of any relationship, so we tried our very best to provide some questions that would offer a few giggles between you both.

Did you have fun going through these questions? Want to continue the laughs? Check out our date night subscription boxes! Each box comes with games and activities that aim to do the same things as the questions above (and yes, they can be just as outrageous)!

Start Your Date Night Adventure Today!
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