Dating Questions You’ll Want To Ask Your Online Match

There’s no doubt about it, we live in an era where online dating is prime.

The online dating culture is here, and it’s here to stay. 

But despite being ubiquitous, I'm sure we can all agree that online dating is a difficult task. It can be uncomfortable and super awkward at times. If you really think about it, you can understand why. 

It’s a process that requires you to decide whether or not you like this person enough to physically meet them - which is a big step. Especially given that during pandemic times, all of your communication has been online or virtual. 

It can lead you to think about the possibility of dry conversation and annoying responses when you finally meet, which is enough to make you think twice. 

So, wouldn’t you say it’s better to be over-prepared than under prepared? 

You can do this by asking the right questions, the ones you really want to know - the ones that will put your mind (somewhat) to rest. 

My experience 

Over the years I’ve used dating apps on and off, and well let’s just say I’ve had a lot of trial and error situations. 

A lot of thinking “maybe the next one” or “I wish I’d known that beforehand”. 

But don’t lose hope. 

There was one tactic I used r to get a feel for the person I wanted to meet up with. 

I would randomly ask a question mid-conversation meaning that they would have to reply and answer the inquiry for the conversation to continue. Of course, I pre-warned them early on in the getting to know each other stage that it was a thing I liked to do - I’m not that mean! 

It sort of relieved some of the awkward pressure of wanting to know things about the other but not wanting it to come across as an intense interrogation. 

In fact, a lot of people would agree it was a fun way to go about the whole situation before meeting up for the first time. 

So what are these fabulous questions I would ask?

1. What are your motivations for getting out of bed in the morning?

Pug dog with blanket over his head

This question is number one.  It’s such a good conversation starter. So throw away that generic “Hey, you’re cute, let’s get together ” and get some depth going right from the get-go. 

I’m telling you, everyone has something that gets them motivated to get out of bed in the morning. I mean they have to - why else would you leave those warm sheets and cozy pillows?

This tells the person you’re trying to connect with that you  want to get to know them, want to learn about what makes them tick. It shows you care, which is never a bad thing. 

2. Who’s your biggest role model? 

A hard, but equally important question. It’s a question that generally does well with the online dating community. 

Everyone has some they admire. From celebrities, entrepreneurs, writers, to parents, siblings and even friends or family. Understanding which influential figures are important to your date is hugely beneficial in terms of connection and engagement. It gives you something to chat about - something that’s important to your date. 

And as a bonus, you’ll score big dating points. 

3. Did you go to college/university? If so, where and why? 

Not everyone has their education plastered all over their dating profile - I mean why would they?

Missing details like this make for great ‘get to know you’ questions. You can dive in deep and find out if they went to one of those fancy ivy-league type schools, or maybe even a party school. 

University library filled with curious students

You can follow up with trying to find out their motivations for going to that school. Was it because of the courses they offer? Or was it because their friends went there and they couldn’t handle being apart?

Knowing something like where a person went to school, and even why they chose the professional path they chose, helps you to see what drives a person to make certain decisions. Understanding what influences their life and trajectory. 

4. What is the weirdest talent or quirk you have?

This is a fun one to find out - that is if they’re willing to confess. 

There’s not one person out there that doesn’t have a talent or quirk of some sort. Whether it be legitimate or funny and embarrassing, we all have at least one. Asking these questions and getting a real answer gives your date the opportunity for your date to shine. 

You’ll know something that’s unique (and potentially entertaining) which probably isn’t known to a lot of people. It will instantly bring you closer and more intimate. 

If they’re actually willing to divulge the answer, then you know they are an open and welcoming person. Just be prepared for the question to be sent back your way so get your answer planned out and ready to go. 

5. What is your favourite book, movie or TV show (series) and why? 

Yes, I know this question is totally unoriginal but it’s a classic - and for good reason. 

To me, as a film fanatic and complete book worm, this question is up there as one of the most important ones to ask. I need to know if this person is going to enjoy binge-watching the same shows and movies as me - ultimately leading to lazy Sundays on the sofa with Netflix. 

Open book and cup of coffee on a bed

This question is a great ice-breaker at the start of your date. It’ll get them feeling comfortable talking about something they’re familiar with and enjoy, Who knows, some of the answers you might share in common!

6. Why are you here?

This question sounds very forward and can be misinterpreted in different ways so let me clarify. 

What I mean by ‘here’ is the online dating space you’ve used to match with this person. You’ll need to ask this question pretty early on in order to help you weed out and establish a person’s dating intentions. Are they just looking for a hook-up and fun? Or are they here to actually find a committed relationship?

It’s important that this is figured out pretty early on so that you’re not wasting your time. You could be looking for  the opposite of what they’re looking for and vice versa. So best to get clarity from the start. 

7. What is your go-to drink on a night out?

Men at a bar having drinks

This  is another pretty standard question. 

But figuring out the other person’s drinking style can be key! This way you’ll have an idea of whether, on your first date you’ll be getting wine drunk, splitting pitchers, tasting cocktails or enjoying a classic ice cold cola? 

As most first dates happen in bars and restaurants it’s important to know which to expect. With the knowledge of what to expect, you’re  prepared and ready for the exciting night ahead. 

Not to mention, once you find out the answer to this question you’ll be more equipped to plan a date suited around the likes of the person joining you. 

8. What does your typical Saturday night look like? 

If I’m honest this is a super low-key and fun way of asking your match “are you a player, party animal, Netflix obsessed, take-out kind of person”, or something else entirely?

Obviously, each answer comes with its own set of pros and cons, but I suppose that this one’s all down to personal preference and taste.

9. What is your favourite type of vacation?

Adrenaline junkie, beach bum or explorer? 

Woman and man swimming amongst fish under the water.

Not only is it good to know what sort of vacation you’d be in for if it works out well between you and your date, but it also acts as a very engaging topic to talk about. 

You’ll get them talking about past travel experiences, perhaps places you’ve been, perhaps places you want to go but haven’t had the chance to visit yet. 

This will give you an insight as to the type of person they are. Whether or not they are adventurous or just content with simplicity. 

It’s helpful to keep in mind that although having someone who likes the same sort of vacations as you, it might also be great to find someone who doesn’t. Hear me out. Someone who you can explore a different way of spending your time on holiday, show you a different way of travel and you them. Sounds like fun if you ask me!   

There isn’t really a right or a wrong way to answer this question. Like most things, it’s all down to how they are as a person, your connection and the vibe given off when talking about it all. 

10. Would you rather have toes for fingers or fingers for toes? 

Silly question I know - but I bet you’re curious to know the answer, aren’t you? 

Random questions like this one are hilarious and they keep your date on their toes… or is it their fingers?

Funny questions are great tools that open the door to telling stories, sharing fears and even making jokes. It helps spark banter between you and your date  and form  some sort of connection. 

This is the time you can really use that imagination of yours and dive in deep with the “what if”. 

Overwhelmed by online dating?
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