3 Must-Ask Dating Questions

older couple on a dateWhat’s the purpose of dating? That’s a big question but ultimately it’s to decide if this person has potential. It’s also your first opportunity to gauge if there’s any pull between you two, if there’s chemistry, attraction, a connection.

But more than exploring the potential connection, having conversations that go beyond the surface also make you stand out and that’s what makes you memorable, and eventually it what makes you (and they) fall in love.

So what do you do? Relationship expert Laurel House advises asking strategic questions that reveal true character, extract their intentions, and expose any deal-breaking red flags.

Best 1st Date Question:

“Why?” 

That’s the question: “Why?” Asking “why” allows you to understand their perspective and point of view. Why do they think that way? Why do they feel that way? Why do they have an interest in that topic?

For example, after you ask, “What do you do?”, follow it up with, “Why did you decide to go into that career?” The purpose of the tacked on question? “What do you do?” may reveal status, true, but in addition to taking up their time and requiring their attention, they choose that career, they decided that they wanted to live that lifestyle, put in those hours, and spend the rest of their days plugging away doing that. What inspired, drove, motivated them to pursue their job? Says something about someone doesn’t it? Then get ready to have the same question reversed on you.

Best 2nd Date Question:

You seem like a pretty amazing person. Who let you go so that I got to go out with you tonight?”

I know, talking about your ex is seriously controversial, but it’s an essential second or even first date topic. Why? Because it’s actually incredibly revealing while simultaneously setting a standard of expectation. It reveals your type, what you were like in a relationship, your current attitude towards the opposite sex, how ready you are to move forward into a new healthy relationship, your comfort with commitment, how introspective and reflective you are, your red flags, etc.

older couple on a date at cafeHere’s the thing though- it’s a two way street. You both have to talk about your exes in order to say “Yes, it’s safe to go there. I’ll show you how it’s done by talking about mine first.” You are therefore setting the expectation as to how much you are going to reveal. BUT be careful. When it comes to ex-talk it’s not about dwelling in the past. The purpose is to learn more about him, reveal more about yourself, be on the lookout for red flags, and hopefully to connect on a deeper more authentic level.

Best 3rd Date Question:

“I love all of your stories, but I am sure there are some pretty significant back stories. Those are what I want to know about. What moments in your life really shaped who you are today?” 

Yes, it’s time to get deep, raw and vulnerable. Drop those walls, pull your guard down, and be prepared to expose a more intimate side of yourselves. This is another “I’ll show you mine, then you show me yours” type of conversation.

By talking about your past pain points and life-changing markers, you are creating an environment of emotional intimacy and trust that makes your date feel safe to share their red flags with you, which you want them do so that you can get a better understanding of who they are and what they have been through. Once they have shared a secret or something about themselves that they generally hold close, you are now in their immediate circle.

The whole dating process is about getting to know each other. I’m not saying that you should throw up your past on the table, or treat it like baggage that you are ashamed of. I’m saying that you tell stories- honestly. Think about what you are going to say, which experiences you are going to share. That’s all part of getting raw. It’s not just about what you did, but why, and what you learned from it.

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