By Julie-Ann Sherlock
Let’s face it, the dating world can be scary, whether you are just starting out or an old hand like me. Putting yourself out there looking for someone to have fun with or spend the rest of your life together is petrifying.
Today’s apps allow you to wade through hundreds of people before choosing a few to engage further and meet in person.
But how do you decide someone is worth green lighting for a date? Safety is a priority, so meeting in a familiar public place, arriving and leaving by your own means, and telling a trusted friend or family member your plans are all important. Knowing the person better online (perhaps having a few video chats?) before going offline should help you feel more comfortable in their company. It may also save you from wasting time on someone entirely unsuitable for you.
But how do you do that? Asking questions that give you some insight into the type of person they are and your compatibility or highlighting any potential red flags or clashes can help.
Here are some questions I (and some relationship experts) suggest you ask before meeting that stranger you have been chatting with online.
Getting To Know Their Background
Do a Google search, verify the photos they have shared are really them, and find out their relationship status before you get entangled in a mess. Of course, it is still possible to be catfished, but if you have their phone number, you can do a deeper search.
My favourite site to check if someone is the real deal or not is, surprisingly, LinkedIn. Most working people have a profile, and because it is for their professional life, they will likely have an actual photograph and details about their education and work life that you can ask them about and easily verify.
So the first question I would ask them to help me with this background search would be: “Where did you grow up/go to school?”
This not only gives you the knowledge to match with their education on LinkedIn but may also give you some insight into their childhood. Was it a rural upbringing with lots of outdoor activities? Or did they grow up in a big city and have many cultural experiences?
Finding out where they lived as a child and now are based may prompt the question: “Why did you decide to move to this city or town?”
This gives you the inside track on where they prefer to live, the lifestyle they like and if they would be willing to move again should you decide to up sticks. There is no point in falling for and getting involved with someone who hates cities if that is where you want to live.
Another window into the type of person they are can be opened by asking: “Tell me about some of your favourite childhood memories?”
This allows a trip down memory lane and will help you understand some of what has made them who they are today. If they have memories that recall feelings of being loved, they are likely emotionally stable and a good bet.
Asking, “Which family members are they closest to?” and “Who are the most important people in your life and why?” can also reveal how they connect with others and their emotional maturity.
Future Proofing Your Relationship
Now that you know a little about their background, it’s time to gaze into the crystal ball and see what they want their future to look like.
To avoid wasting time, ask early in the process, “What are you looking for from dating?” to help weed out the F**kboys from potential boyfriends. If they respond that they are looking for something serious, then you can ask, “What are your views on marriage and children?“. If their answer aligns with what you want, you know there is some hope of success.
These questions can lead to others that may reveal more about them, such as, “How do you handle conflicts in relationships?” and “What are your relationship pet peeves?”. These two questions will allow you to discuss communication methods, likes and dislikes etc., so you can go on a date with a clearer picture of who they are in a relationship.
Before you go all in and start planning a wedding in your head, asking, “What are your long-term goals and aspirations?” can allow you to see if your future plans align or if you will struggle to find a way forward.
While these questions are not a magic door into the perfect relationship, they will let you meet someone new with your eyes wide open about compatibility on some important stuff. If your answers match enough for you to proceed, then you can get to the fun questions like “What’s your favourite food?”, “What type of music do you like?” and “what is your ideal date?”
Be safe, be smart and have fun out there!

