Must-Ask Questions Before Dating


Dating is fun, but it is also expensive and time-consuming. In this day and age, thanks to the internet, we have opportunities to meet people from all walks of life, far beyond our immediate social circles. We cannot possibly date THEM ALL. So to narrow the list down, I’ve always found that chatting to someone online or texting them is a great way to get to know them better first. It’s a time saver and it’s the best way to decide if you want to take things further.


Credit: Light the Minds

Here are some of the must ask questions which will reveal much more about his character, past experiences, and personality.


What was the most awkward date you’ve had?

This is a great icebreaker which is actually quite fun to share. It will give you both a laugh. It gives you the opportunity to share with him your past bad date stories as well. Plus if you do end up on a date with him, you will know what to avoid so things won’t be as awkward.


What’s your favourite / least favourite quality about yourself?

It would be interesting to see how he describes his best trait or major weakness. You can also gauge how confident and truthful he is, and you can also gain an insight into his self-esteem. Perhaps his virtue is his honesty and if you’re the kind of girl who values honesty and prefers a straightforward kind of guy, then you’re in luck! If his flaw is that he’s a workaholic but you know you’re the clingy and needy kind of girlfriend. Drop him.


What do you look for in a woman?

It’s important to find out what qualities attract him. It may not be a concrete list set in stone, but it will definitely give you a good idea of what his ideal woman is like and whether you are in the right playing field. I mean if he talks about wanting a woman who can cook, manage the home and raise a family… but you burn toast, don’t even wash your own dishes and would much rather have a flourishing career can clean snot off your child’s face… then he’s probably not the man for you. Don’t waste your time.


What are you most afraid of?

Men tend not to share their vulnerable side, but they all have it. Having to act tough and unbreakable is quite tiring, so it can be a relief for him to be able to share his fears with someone without being judged. Finding out what he is afraid of will help you get to know a side of him that he may not have revealed before.


What do you indulge in/spend too much money on?

It’s not polite to talk money with someone you’re just getting to know. But I feel that questions which centre around indulgences are ok. And they will give you an insight on his financial situation, how he manages his money and the kinds of things he likes. It does make a difference to me whether he likes spending on the finer things such as luxury watches and travel or things which are more frivolous in nature such as clubbing/alcohol or gaming.