Crucial Questions To Ask BEFORE The First Date

2020 has been the year of the text, I'm sure of it. Never before have we had to lockdown and rely solely on tech to get us our socialization fix.

According to the Pew Research Center, approximately 30% of adults had tried online dating in some form in 2019. Since the spread of Covid-19 and the lockdowns, numbers of subscribers to dating apps exploded. Match Group, who owns the majority of the dating app market reported a 15% increase in new users for the months of April-August 2020 and even Tinder saw a record breaking 3 BILLION swipes on March 29th. OKCupid saw a dating increase of 700% while Bumble reported a 70% rise in video calls.

This said, people were clearly trying to make a connection this year and when you can't meet up in person, you're sure to spend a lot of time texting and video chatting so, how do you get that ball rolling? Here are some simple yet tried and true questions that you can use on a potential date to find out if your lifestyles will be compatible once we're safely allowed to roam free.

I probably don't have to say this but if you want a reply back - it's probably best to figure out how to weave these questions into your conversations naturally. Don't just outright slam them with questions - it's a turnoff and will probably freak them out at the very least to be asked potentially invasive questions by someone who is most likely a stranger.


If they have no hobbies or struggle to come up with an answer, that's not necessarily a red flag. It just may be a sign that they're very into their job or don't consider what they like to do in their free time a traditional hobby. For example, if you ask my husband what his hobbies are he can rattle off a dozen including woodworking or playing golf. For me, my 'hobbies' are watching Bravo and playing with my daughters or scrolling Instagram and sending memes to friends. If asked directly what my hobbies are - I'd have a difficult time actually answering.

How to ask this question: What did you do last weekend? In a pre-covid world, how do you like to spend your free time? If you had an entire day off with no responsibilities, what would you like to do? And be ready to answer the question yourself in return!


This one is tricky. You can't outright ask someone if they have mommy/daddy issues or if they have a trainwreck sibling but you can glean a lot of information by asking gentle questions that unless they've experienced a major trauma like the recent loss of a family member, you'll be able to learn a lot. It's important to know how a potential partner interacts with their family. If you're someone who likes to sleep in on holidays and lounge around the house all day and their family runs a 5K every year - you're gonna have a bad time.

How to ask this question: Do your parents live around here? How often do you usually get together? What are some of your holiday traditions? - I KNOW these seem like jumping the gun and assuming you'd be invited to participate but it's important to gauge. If this ends up being forever - you'll have to not only find your place in their dynamic but also balance it with your own families expectations.


I'm not just talking about cigarettes or ooh lala movies. You could be like a friend of mine who met a guy in the spring and fell in love only to become a 'football widow' in the fall. Her man was O B S E S S E D with football and it consumed him four days a week - not counting time spent on Fantasy Football. They're married now and she's learned to enjoy that alone time and find things to do for herself and now with their children but it can be eye opening to find this out about someone once you're already committed.

How to ask this question: What do you think most people would say you spend too much time doing? Asking this way might be very telling - if they answer with, "my ex said I spent too much time in the gym" then you'll know you either have a gym buddy or have someone you've lost to the free weights every morning instead of snuggles.


When I met my husband, he'd never had a dog. Not that he wasn't against dogs, he just happened to grow up in a cat family. These subtle cues are good insights into their lifestyle and character. People are usually pretty open and able to discuss this freely, I think flat out asking is the best way to ask this question. A friend of mine dated a guy who was allergic to cats, and she has two cats. He'd always load up on his allergy medicine before coming to stay for the weekend because she was worth it but that's definitely something you'd need to know about a potential partner before wasting your time. If they hate dogs and you already have one, you know it's not going to work out.


This one is crucial. If they don't have any friends they're going to suck up all of your time (unless they have a ton of hobbies as mentioned above). But also you have to ask yourself why don't they have friends? Are they annoying? Are they rude? Do they not reciprocate in a relationship? All of these are things you'll have to contend with should you decide to get serious. Another thing, if they don't have a social circle, your circle becomes their circle which can get tricky should you have to separate. On the other side, maybe they have a very active social life and you might find yourself dating someone who has a standing tradition of partying on Friday night with their buddies or someone who has regular happy hours with their coworkers or Sunday brunch every week with the girls.

How to ask this question: Tell me about your best friend(s). What do you like to do with your friends? What do you think about having friends of the opposite sex? All of these are important things to know before blending your life with someone else.

With all of these questions and their resulting responses, ask yourself, "Does this mesh with ideas and visions I have for my future?" It's never too early to ask or answer these questions because ultimately, you'll save yourself a lot of wasted time and a lot of heartache if you know right from the beginning that some of your non negotiables (family/pets/etc) don't line up with them. You don't have bend or make someone bend to fit your life - find someone who fits. As I said, never before has the dating pool been so full, keep on fishing!