Blog, dating

Hilarious Dating Questions

Going on a date can be very scary – especially a first date. You find all those butterflies in your stomach turn into dragons and make it hard for you to function as your normal self. Which means, when you both sit down to start your date, you might find it challenging to know what to say to each other as your mind goes blank.

Well, not to worry, as to help you out we’ve put together some of the most hilarious and fun questions that you can ask your date. As, regardless of whether you’re looking to break the ice or make your date laugh, just try a few of our fun dating questions:

1: If You Were Trying to Make a Cashier Uncomfortable, What Items Would You Bring?

Although you shouldn’t really mess with people just trying to do their job, it’s certainly fun to think about scenarios where your purchases might raise a few eyebrows. Such as going to the checkout with a knife, rope, bleach and lots of black bags.

This kind of fun question gives you both plenty of opportunity to try and outdo yourselves creating more and more fun ways you could scare those around you with your purchases. It’s also gives you both the chance to see if you have a wicked sense of humour that matches each other.

2: What’s Your Guilty Pleasure TV Show?

We all have at least one TV show that we watch but know it’s a bit daft. It could be My 600lb Life or Keeping Up with the Kardashians, either way talking about the silly shows you both watch will have you both giggling and reminiscing about all the TV shows you’ve watched over the years and how ridiculous they were.

Even better, you both might find you watch the same shows, which means you could find yourselves arranging a date to watch some guilty pleasure TV together in the future.

3: What’s the Weirdest Thing You’ve Seen in Someone’s House?

Most of us have seen something freaky in someone’s house before. It could have been an exceptionally creepy doll that your gran used to have, which you feared would come alive at night. Or perhaps your ex collected something strange.

Whatever you’ve seen, your date and you will likely be in hysterics as you tell each other about all those strange items you’ve seen over the years. You might even be willing to admit about something weird that you have in your home and how you required it.

4: What is the Least Sexy Name Out There?

There’s no denying it, there are some names and combination of names out there that just aren’t very sexy. Which makes for the perfect opportunity to break the ice with your date as you both try to think of the most unsexy name possible.

Just be careful that you don’t use your date’s name in your examples!

5: Have You Sent a Message to the Wrong Person Before?

It’s something we all fear, you’re sending a message or text to someone where you’re talking about someone else. Instead of sending the message to your friend, you accidently send it to the person you were talking about – which leaves you in a very embarrassing predicament.

While these might be some of your worst memories imaginable, they make for a wonderful talking point for a date that you can both laugh about. Even if you haven’t done it yourself, we often know someone who has, which you can happily make fun of them for!

6: If You Got Arrested Right Now, What Would People Presume You Had Done?

It could be for being drunk and disorderly, stalking a celebrity or perhaps for accidently shoplifting as you’re so forgetful. Not only is this question fun as you both discuss those crazy qualities that you have that could get you in trouble, it also gives you a deeper insight into the date that you’re talking to.

Of course, if you’re date answers that their family or friends might presume you’d been arrested for being a serial killer, you may wish to rethink your plans for having a second date.

7: If You Change One Word in a Popular Movie, Can You Totally Change the Plot?

This sort of question is ideal for a first date conversion tips, as it can help break any awkward silences but doesn’t feel like you’re probing too much into what makes your date tick. Instead, you can both spend the time laughing and giggling away as you both think up more and more ridiculous movie titles and how much they would change that movie.

8: You’re Wrongly Admitted into an Insane Asylum – How Do You Convince Them You’re Sane?

In reality, this would likely be the worst nightmare for many of us. However, on a first date, creating wild and crazy scenarios for how you would prove your own sanity can be incredibly fun for you both. Plus, you’ll likely learn a lot about each other without even realising it!