First dates are a real tricky business, aren’t they? You know the drill – you don’t want to cut straight to the chase and scare him away with invasive questions like how many kids he’d be open to having with you, but you want to figure out what his deal is and where he stands in terms of relationship readiness. If you’re dating to find real love, then asking these 10 questions should help you figure out if he’s on the same page:
Why did you decide to ask me out?
Aside from you being reeeeeaalllyyyyyy curious as to what made him pick you, his answer to this question will tell you a whole lot about how he views you. If he’s talking nothing but a great boobs & buns game, it’s unlikely he sees a real romance ahead. If he mentions something to do with your personality first, you’re off to a FABULOUS start.
What are the qualities you look for in a girlfriend?
This one is good because not only will it tell you what he values in a partner, it will also allow you to compare his list with your own and see how well they match up. If words like kind, generous, caring, and loyal make an appearance, that is a GREAT sign. But he could always be a sneaky jerk looking to get laid, disguised as a genuine, kind-hearted man. Tread carefully.
What’s the most thoughtful thing you’ve ever done for someone?
This will give you a great insight into his personality, specifically how romantic or thoughtful or creative he is. This, in turn, will show you how much time and effort he puts into making other people happy, and how important this is to him. Long term, you want someone who is selfless and wants to make sure that his loved ones are well-looked after.
Have you ever had your heart broken?
Automatically, you’ll find out if he’s ever been mad crazy in love before, which strongly suggests that he has a heart, and is not emotionally unavailable (yay!). His story will also show you a raw and vulnerable side of him that he probably doesn’t show often or to many people. If he does open up to you this early on, this tells you he naturally feels comfortable around you and wants to share a deeply personal part of himself with you. Being your true self and not being afraid to show weakness occasionally is the sign of a man who is mature and sure of himself.
Have you ever cheated on a partner or been cheated on?
If you do happen to unfortunately be on a first date with a serial douchebag, it’s highly unlikely he’ll willingly confess to being a player. But what you should be listening out for is what he says after the yes or no part. What is his honest opinion on cheating? Does he judge cheaters harshly, or does he have more of a relaxed view on it? These are all subtle clues that you need to collect on a first date if you’re looking for something real.
What’s your biggest goal in life right now?
His answer to this question will tell you what stage he’s at in his life right now. If he’s talking about ‘having fun’, and sounds generally unfocused, then he’s likely to be similarly blurry when it comes to a relationship. Pay attention.
How many serious relationships have you had?
If he’s never been in a serious relationship, it’s a potential red flag that he won’t be emotionally experienced enough to maintain anything long term with you. Having said that, he might just not have met that special someone yet who he wants to take that step with. As a general rule, the older a man is, the more apprehensive you should be if he hasn’t had a serious relationship. On the flip side, if he gives you a number over 10, you need to question what he defines as “serious.”
What does a successful relationship look like to you?
This will give you an insight into what his past relationships have looked like, what he learned from them, and what he views as important. If he manages to give you an answer that mentions best friends, communication, or teamwork, it’s a great sign that he understands the work it takes for a relationship to thrive and is more likely to be prepared to put in that time and effort.
Where do you see your life in ten years’ time?
If his answer speaks ambition, drive, and a sense of sureness, then even if he isn’t currently where he would’ve hoped to be at this point in his life, it’s an indicator that he has at least a rough idea of where he wants to go and how he plans to get there. He doesn’t need to have every hour mapped out by any means, but a sense of direction shows that he thinks LONG TERM and isn’t afraid to.
Do you want to settle down someday?
I know a lot of articles out there will adamantly tell you not to mention kids or marriage because you’ll just scare the poor bloke away, but I think that is TERRIBLE advice. If you are a girl who absolutely wants to get married and have kids someday, then you owe it to yourself to find out if the person you’re dating wants that too. There are so many ways to broach the topic without putting any pressure on him. If you’re looking for a serious relationship, then you need to know if the man opposite wants the same things from life that you do. Time is precious – don’t waste it dating someone who will never be able to give you what you know you want.
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