You cannot talk about dating in this day and age without a mention of online dating. We seem to have left the traditional process of looking for Mr Right (or Miss Right) for computerized shortlisting systems. There are lots of applications to choose from, all with a different twist to what they have to offer, and it seems like there are new ones popping up every day. While there may be varying opinions as to whether dating online is right or not, it really is part of our culture today. People are making billions of dollars off online daters and daters are absolutely loving it. It is pretty safe to say that online dating is here – and here to stay at least for a while.
I did say that online daters are loving it, and they are, but that is not to say that it is easy. The computer does most of the elimination process for you but you still have to do some work yourself. You have to find a way to determine if the matches the computer gives you are people you would actually want to spend a few hours with on an actual date. The best way to do that is by asking questions. Not just any questions, though, but the right ones.
I have some experience with Tinder which is arguably the most popular dating application right now. Before going out to meet one of the guys, I always make an agreement that we would randomly ask each other questions and the other would have to answer honestly. I must admit, it was quite a bit of fun. It helped me get to know him, so even when we went out for the first time, I felt like I already knew him.
This could always help avoid those awkward silence moments on a first date because the ice would have already been broken.
Before we dig deep into which questions you could ask, here are some techniques you could use to improve your communication with your potential Tinder date:
- Acknowledge their answer to your question but do not dwell on it for too long.
- Give some information about yourself. Assume that the same question was posed to you and answer it.
- When you transition to the next question, always make sure that it somehow flows or connects with the previous one. This way, your match will feel like they are in a friendly conversation and not an interview of some sort.
Here are a few questions you could ask your match before you meet up. You can ask these as they are or use them to get ideas of more appropriate ones depending on what you have learned about them.
I have batched them up into four groups: personality based questions, questions to do with their past experiences (I call this yesteryears), questions about what they like, and random, hypothetical questions. You can quickly jump to the ones which will reveal information you are most curious about.
1. What Drives You?
Getting to hear what motivates them enough to get up every morning tells you a lot about who they are and what they believe in. It is a somewhat serious way to start a conversation but if they do not mind sharing this information with you, why not explore this line of discussion? This kind of question makes your match feel that you are genuine about wanting to get to know them beyond their physical looks.
2. Which Time Period In History Would You Like To Have Lived In?
On the surface, it seems like an idle-minded question but it can be very interesting to hear a guy’s answer, especially if he knows his history well. Whichever historical era he relates to, it will tell you something about what he aspires to be or to do. If he mentions the Industrial Revolution, then he is probably an entrepreneur at heart. If he would have liked to live in America in the sixties, then he is probably interested in matters of civil rights and equality. If he answers “Honestly, I think the current information age is the most fascinating time of all”, then he is probably a tech buff who keeps up with all the latest technologies. Well, either that or he has no idea what to say about all those past eras the history teacher kept going on about. This is an interesting way to get a sneak peek into who your Tinder match really is inside.
3. Who Do You Admire Most and Why?
First of all, if his answer to this question is “My Mom” you probably will not go far with this one. You can learn a lot about a person by hearing who they would like to emulate and most importantly, why they admire this person.
4. Do You Believe In The Existence Of A Divine Being?
Be careful with this one, it could be a sensitive topic and you could be opening a can of worms. On the other hand, it could be a great way to get to know your match. Should they be open about their beliefs, you can learn about their value systems and if these are anything close to yours.
5. Which Kid Were You In High School?
There is no denying that there seem to be some pre-scripted categories of kids in every high school. There are the goodie-two-shoes kids who never once cut class or submitted an assignment late. There are the nerdy kids, the outright ill-mannered ones, the mischievous, sneaky ones and the list goes on. Ask your match which kid he was in high school. Did he ever cut class to make out with a girl in a storeroom? Was he a student leader? People do not really change that much and personalities usually remain the same. So, who he was in high school will tell you something about who he is today as well.
Share some of your own high school experiences too. Telling these stories is not too personal so you feel safe even if you are not yet free enough to share more personal information.
6. What Is Your Most Unusual Trait?
We all have talents which we are happy to talk about even to a stranger. That is not what you are looking for. You want to hear that one strange trait which your match would not talk openly about. The point is not the actual information he gives, but rather the person’s willingness to share it with you. Have fun with this one and you do not have to restrict yourselves to just one unusual trait.
7. What Cause(s) Are You Passionate About
When someone is passionate about something, they subconsciously jump at the opportunity to talk about it. Their faces light up, they speak more confidently and they genuinely like it when you ask questions about it. If you are talking on the phone or chatting online, the passion will be evident. What a person feels strongly about tells you a lot about them.
8. What Are You Interested In?
What your match is passionate about is not necessarily what they are interested in. Share some of your own interests as well. Find out if you have any common interests or any stark opposites.
9. Why Did You Opt For A Dating Site?
Finding out why your match decided to try a dating site will tell you what their intentions are. Are they looking for a quick and uncomplicated sex buddy or a committed, perhaps long-term relationship? Whichever the case, no one should be judged. It is up to you to establish if your match is looking for the same things that you seek. If he is, you are indeed a good match.
10. Where Is Your Family? Do You See Them Often?
Even if your match lives miles away from his family and only gets to see them at Christmas, it will be useful to hear him talk about them. You will get a good sense of whether they are close and if he values the relationships. If you are big on family, this will be important information for you.
1. Describe A Typical Saturday Night For You.
He may not get where you are going with this question, but you really want to know if he is the kind of guy who considers going out and getting dead drunk a fun way to spend a Saturday evening (well, Saturday evenings and early Sunday mornings). If not, is he the kind who will happily order in for dinner and binge watch movies on Netflix until the sun comes up? Not to say that either personality is better, you just have to figure out what comes closest to your typical Saturday night.
2. Describe Your Idea of a Perfect Day.
He likes to start his day off with an early morning run followed by a few hours of meticulous gardening. You long for your days off because that is when you sleep in and then spend the day watching movies with a large bag of potato chips. Oh, and you would pay anything not to get your hands dirty. Clearly, you are different but sometimes dating someone starkly different from you is fun and as the saying goes, opposites attract.
On the flip side, if he describes a day that is exactly your kind of perfect day, now you know what you will do on your first date.
3. What Is Your Default Drink When You Go Out?
This is a pretty important detail. It tells you how their ideal evening out typically unfolds. Is it a bottle of wine, a bottle of whisky, a can of ice-cold cola or a couple of beers?
4. What About Me Stood Out For You?
This question further interrogates their intentions and attempts to link them to you as an individual. What was it about you that made them feel that you might meet their intentions? If they cannot come up with anything specific to you, then they are probably just randomly trying their luck with you.
5. What Is Your Idea Of A Perfect Vacation?
Does your match like to laze around on the beach or do they prefer an active kind of vacation? If things work out and you end up together, a few years from now, will you be saving up for a beach holiday in Hawaii, a hiking vacation in Chile, or a safari in Kenya? You can also talk about your previous vacations and what you liked or did not like about them.
6. Where Would You Like To Travel To Next?
Travel stories can be a great way to get the conversation going. They can be very interesting and are not too personal. Compare experiences from countries you have travelled to and get to learn what it is that fascinates your match. Is it foreign cuisines, histories of different countries, lifestyle and cultures, whatever it is, it tells you a lot about your match.
1. Where Did You Go To School?
Most people don’t include this information in their profile. It will be interesting to hear where your match went to school and how they ended up there. Did they go to an Ivy League school, community college, or none at all? What was their major and did they enjoy the whole experience?
2. What Was Your Childhood Answer To ‘What Do You Want To Be When You Grow Up?’
We all had a perfect answer to this question when we were little. Answers were based on our parents’ lines of work, an aunt or uncle we admired or something we saw on television. What did your match want to become?
3. What Is Top On Your List of Embarrassing Stories?
Some people simply cannot recount an embarrassing experience to a potential love interest because they feel that it makes them less of a man (or woman). Talking to someone who is confident enough to tell the story and laugh at themselves can be fun. Embarrassing stories are always funny so they also bring out the person’s sense of humor.
4. Are Your Grandparents Alive? What Are/Were They Like?
No one ever has negative things to say about their grandparents so they are a great place to start if you want to hear about a person’s family. Even if his grandparents are not alive, most people have fond, childhood memories of their grandparents. Some people will be happy to give you some history of their family. All these are a great way to feel emotionally close to someone, albeit for a time. It also helps to ease any tensions before a first date. You feel like you already know the person and you are not meeting them for the first time.
5. Did You Enjoy Your Last Tinder Date?
Dating on Tinder, or any other online dating site for that matter, makes you interact with all kinds of people, most of them weirdos (maybe that is just with me). If you are not too hung up on finding your one true love on Tinder, you might have some pretty interesting experiences. It will be fun to share these stories and to hear another person’s experiences as well.
Boring guy alert: If all he gives you is a one-word answer to this question like “Yes” or “Naah”, he is probably not into fun storytelling.
6. What Was The Most Interesting Job You Ever Had?
It does not matter if it was a two-hour gig or a permanent job. People do some crazy things for money. Maybe he spent a couple of months waiting tables at a zoo café or worked as the buffed doorman at a club. Hearing about what people have done to earn a few bucks does not necessarily tell you much about the kind of person they are today, but it definitely makes for interesting conversations. It could also be that he is a rich kid who has never had to work for money, then he could potentially be spoiled.
7. Which Of Your Achievements Are You Most Proud Of?
It is always great to hear someone talk about things he or she has accomplished because you also get to understand why they feel that it is such a big deal. They may have other accomplishments which you or others think are a big deal but what they consider important tells you a lot about their values. Letting someone talk about themselves makes them feel good about themselves too. If they like your company on the phone, they will most likely want to meet you in person too.
1. What’s Scarier: Swimming With Sharks or Sky Diving?
This kind of hypothetical questions can be fun because they pave the way for interesting stories which reveal the person’s fears and maybe even their fascinations. If neither of you is uptight about it, you can make jokes about what you are terrified of and what you can’t get enough of.
- Discover more: 15 Great Hypothetical Conversation Starters
2. I Have Five Items In My Refrigerator Right Now: A Beetroot, Chocolate, An Egg, Some Cheese and Ketchup. What Can You Make For Me?
Make your match put on their thinking cap to come up with a meal or snack idea using the ingredients in your refrigerator. They will be lucky if you like to cook and you just filled up your refrigerator with supplies this morning. If all you have are some random items, they have no choice but to get creative. If he can come up with a few decent ideas, why not invite him over to prepare the meal in person for you? It will be a fair exchange if you supply the ingredients while he puts in the work.
Perfect Timing Does Pay Off
Coming up with the perfect questions to ask your match is only half the work. The battle is won when you identify the perfect time to ask them out. If you do it too soon after you started chatting, you come off as desperate. On the contrary, should you wait it out too long, you may just miss your chance because they might get bored and move on to another love interest.
The best thing about dating sites is that you can use technology to quickly come up with a shortlist of people who are most likely to be ‘the one’ for you. However, it cannot do the rest for you. You have to come up with a way to get to know a person well enough to determine if you want to date them or not. These questions are a fun way for you to come up with your own ‘second level shortlist’.