The Best Dating Sites of 2021

3 Online Questions You Must Ask Before the First Date

By Laurel House


The initial email exchange during online dating messaging is much more than just an opportunity to find someone to go on a date with ASAP! Unless of course you want to leave it to chance? But I’m not sure that sitting across a total stranger who you briefly met online, without much knowledge about is the right approach. I mean, what if within moments you recognize that their is going to be a wasted date because in no way are you a match?

Instead, initial messaging through online dating is one of the best opportunities to determine whether you are interested enough to commit to that in-person meet-up or not.

So what do you talk about and what questions should you ask in order to increase your chances of a successful date and decrease those “ugh!” instances where you know you’re doomed at the first face to face glance? It’s all about digging in, asking smart questions and extracting important information about who they are, how they became that person, where they are going in life, and what their dating purpose is.

Sounds very time and energy-draining? Well yes, you are doing a bit more work on the front end, but it will save you loads of dating time and energy, and save you from an awkward date and disappointed feeling about online dating as a whole.

Hey, we are here to help and these are our 3 Online Questions You should ask right from the beginning:

QUESTION 1: What do you do and why?

“What do you do?” may reveal a lot about their personality and career path. Depending on their job, you should understand if he works many hours, what their priorities are, what their daily professional routine looks like and how much their career dictates their day to day life. I call it “Career-Typing.” It’s a “type” generalization that reveals much more than their, clothing style, car, height, and looks. You are also seeing their work-attitude, their passions and what propelled him to want to go into that certain career in the first place.

What to ask before the first date

QUESTION 2: Tell me 5 random things about you.

Unless he takes it as a joke, he will likely think about their one for a second and tell you some pretty interesting and introspective and revealing things.

He may share their education, honors, lifestyle, upbringing, talents, idiosyncrasies, taste, social status, or quirks. It may also reveal things that are on your must-have or won’t-stand list that will immediately turn you off or on. The answers to their question may be the time that you decide to stop responding to him and move on, OR make you even more intrigued.

Here’s an answer I got from an optional date:

“1. No brush or comb necessary as after showering, I can throw some gel in my hair, and voila, it's ready to go. 2. I can tie a cherry stem with my tongue. 3. I'm a poor singer, but enjoy karaoke so long as it’s a private room 4. I try to have a dark piece of chocolate everyday 5. I like to dance, and really enjoy classes, but still haven't mastered free form.”

What can their answer say about him?

“I too am a poor singer, but will consider it if in a private room”. I love that he enjoys dance classes, which shows that he is open to learning new things and doesn’t mind looking silly in front of others. The cherry stem thing says that he has a very flirtatious and sexual side.

QUESTION 3: How have you changed in the last 5 years? Where do you see yourself in the next 5?

It might sounds a bit upfront and heavy to ask their question, but you can learn a lot from the answer. their may show if he is introspective, if he learns from mistakes, if he is self-aware, self-critical, if their ego is in check, what he is looking for, and what their experience level is.

Sample (and real) Answer:

“Good question. I believe that I've grown to place more importance on friends / family, although they've certainly always been very important to me. I have evolved in terms of the relationships I have; I'm a bit of a late bloomer in that area, and 5 years ago (maybe a bit longer), the relationships I had with women were less serious and meaningful than the ones I've had in recent years. Over the next 5 years I'd like to start a family (assuming I meet the person I want to start a family with), professionally I'd like to see my business continue to develop (I won't bore you with the goals), and I'd like to continue to be very close to my family and friends.”

Take Note:

It’s the “and why” or “and how” part of the question that is essential. Go beyond the fact and into the reason behind it. You can truly take any mundane topic and find its depth if you just do a little digging. Even when it comes to the question “What’s your favorite ice cream?” If you don’t ask “and why?” you will likely get an answer like “French Silk Ice Cream”- which must have a story to it since it’s kind of an obscure favorite, but you didn’t ask “why.” Or worse, the answer could simply be “vanilla”- something so plain and so easily judgeable that you might even be inclined to shut them out right then! But what if the “why” is because they are “obsessed with toppings and vanilla is the perfect blank slate”? That’s a pretty interesting and compelling reason to let them stick around.

So remember, before you rush to just set that date with that person you barely know, take some time to ask them these questions. They reveal a lot of information that will help determine if your next step is to meet face to face or not.

Haven't found the right dating site yet? Have a look at our Comparison Chart to find the online dating site that suits you best.

Advertising Disclosure

This site is a free online resource that strives to offer helpful content and comparison features to its visitors. Please be advised that the operator of this site accepts advertising compensation from companies that appear on the site, and such compensation impacts the location and order in which the companies (and/or their products) are presented, and in some cases may also impact the rating that is assigned to them. To the extent that ratings appear on this site, such rating is determined by our subjective opinion and based on a methodology that aggregates our analysis of brand market share and reputation, each brand's conversion rates, compensation paid to us and general consumer interest. Company listings on this page DO NOT imply endorsement. We do not feature all providers on the market. Except as expressly set forth in our Terms of Use, all representations and warranties regarding the information presented on this page are disclaimed. The information, including pricing, which appears on this site is subject to change at any time.