Ahh, first dates. Going out with a stranger whom you may or may not hit it off with is the stuff of social anxiety nightmares, but it sure is one hell of an excitement at the same time!

Every first date is different. But the gist of it is always pretty much the same. 

You agree to meet somewhere public, preferably with ambient lighting so that it’s bright enough to get a clear picture of what your date looks like, but not too bright that your pores are getting all the attention. 

First dates can go many ways. Some are filled with effortless laughter, banter, with some heavy eye contact. Indeed, those are archived in the best first dates section and make it to date no. 2.

Then, you also have the cringe-worthy first dates where moments of awkward silence ring louder than the music playing and all you want is for it to end before you explode with anxiety!

We don’t want to burst your bubble or freak you out before your date, but the latter scenario is usually what happens on first dates. It’s what’s expected when you put two strangers who don’t know a single thing about each other in a room together. 

Moments like these, a little preparation is key. And to help you prep for your date, we’ve assembled a list of best first date conversation starters (including flirty first date conversation starters) that will get you through any awkward silence! Let’s go!

Best first date conversation starters

1. How was your day?

Simple yet effective. 

Firstly, it shows that you care about their day. Secondly, you get a snippet into their life, which also allows you to identify commonalities or if there’s a sliver of connection between the two of you. Thirdly, the answer opens doors to a stream of conversation from both sides as the date progresses. 


2. How do you spend your weekends?

If the date goes well, you’re probably going to be spending some weekends with them. 

This question will not only help you find out your date’s hobbies and interests, but give you an idea of how those weekends might look like. 

And if you like the sound of their weekend plans, it could also be a cheeky segway into setting up your next date!


3. If you could travel anywhere right now, where would you go?

You probably have your own list of places you’ve travelled or wish to travel to. 

Ask your date this question to see if any of their top travel spots align with any of yours. 

Imagine finding out that you both love raving and you’ve been travelling to the same festivals and you could’ve met sooner! 100% an ice breaker and conversation booster! 


4. Talk about their D

Get your head out of the gutter, we’re referring to their drinks!

An easy way to spark a conversation when you can’t think of anything else. Is your date more of a cocktail person? A beer connoisseur? Or a cafephile?

This question can also help you determine your next date idea. Cafe or bar hopping? Why not both?


5. What’s something I wouldn’t guess about you?

Cheeky, mischievous, and a great question to further melt the ice.

Whether it’s a tattoo they regret or a weird fetish, this question can go both ways. Your date has the freedom to spill as much or as little as they like. 

How they reply to this question can also give you an insight into how the date is going.


6. What’s the bravest thing you’ve done?

First dates are terrifying. It doesn’t matter if you are a heavyweight champ or a seasoned surgeon, you’ll still be perspiring like a Chloe Ting workout. 

Asking your date this question will help them relieve a brave moment and give them a boost of confidence. 

Soon enough, the conversation will flow even more effortlessly that you can even engage in more lingering eye contact.


7. Who are the top 3 most significant people in your life?

These might be the people you will be hanging out with if your date makes it through the subsequent rounds, don’t you want to get to know them?

You can also tell whether your date is more of a loner, a family person, or if they have anyone around them at all. 


8. What kind of music are you into?

Music is a big part of most of our lives. 

If you are someone who curates a playlist for every occasion, then you’d surely want to find out if your date has the same appreciation for music. 

Even if they don’t, maybe it’s something that can help you to get closer as you open their eyes and ears to the art of music!


9. Are you more of a cat or dog person?

Whether your date is more of a dog or a cat person can tell you a little bit about their personality.

According to this study, ‘dog people’ tend to be more energetic, lively, and outgoing. Whereas cat people are more laid back, introverted, and sensitive. 

Maybe the person sitting across from you doesn’t even like animals! In any case, at least now you know!


10. Any bad date experiences?

Bringing up exes is a bad idea, but laughing about disastrous dates make for great banter.

Laughing about past bad date experiences together also takes whatever pressure you both might have going into your date.

Nothing beats the last time you thought your date was leaning in for a kiss that you passionately closed your eyes only to realise he was just picking something off your hair! 


11. Is there anything you don’t eat?

Food is life. It will definitely come up sooner or later. 

Finding out if your date has any specific dietary requirements is necessary to steer clear of any awkward dinner date moments.

Besides that, you will also learn if there are any significant ethical or lifestyle differences between the two of you.


12. You won the lottery! How will you spend it?

The way your date answers this question can help you determine their level of maturity and also find out what is important to them. 

Will they blow it off on frivolous things or invest in a company they’ve always wanted to own? Does it align with your own goals and aspirations?


13. What’s your dream job?

Source: Inc. Magazine

Not all of us are lucky enough to be working our dream jobs. 

Your date will appreciate it more when you ask about their dream job than just the usual conversations about work (boring!). 

It also shows that you don’t just want to find out what they do for a living, but you want to get to know their personal and/or professional interests on a deeper level. Dream jobs are usually more exciting to talk about than regular jobs anyway. 


14. Any pet peeves?

Source: Sierra Keller Meyer

Everyone has a pet peeve. Some are reasonable like obnoxious chewers or slow walkers. 

And you also have the really specific, and kinda weird ones like someone who can’t stand fuzzy fruits or who can’t stand their name being misspelt. It’s MICHAEL, not MICHELLE!!

Now that it’s out in the open, you can learn to avoid eating fuzzy fruits or misspelling their name in the future.


15. Do you have any passion projects?

Maybe your date has its own podcast or a popping Instagram cooking channel with 100k+ followers! 

That’s pretty cool, and definitely something you would want to know about!

And if they don’t have anything going on at the moment, that’s fine too. Perhaps you can start a passion project together?


16. Peep what the couple next to you are doing

Gossip can help people bond quicker than anything, but don’t be too mean. 

Come up with hypothetical scenarios of what you think might be happening at a nearby table, that’s always fun! 

Or just keep it even lighter by talking about lookalikes for instance “doesn’t that guy look like George Clooney?” or “doesn’t that lady look like Jamie Chung?”

If it turns out to be George Clooney, great! If it isn’t, it’ll still have softened the mood a little, and hopefully calms your nerves too. All the while keeping the flow of the conversation. 

You can also pivot this topic into the general realm of celebrities! That’s always a light, relatable topic to fill the silence. 


Are you more of a talker or a listener? 

Unfortunately on dates, you don’t really have a choice if you don’t want the conversation to run stale. You also want to get to know the person sitting across from you as much as possible.

So, use our list of the best first date conversation starters above for some pointers and inspiration to practice for your next date! 

Always remember! It doesn’t matter if you accidentally said something silly (or two) on your date because there’s definitely someone out there who’s said even worse!

Need help setting up a date? 

Visit Sugarbook today so you can put your polished conversational skills to practice!