7 Awkward (but brilliant) First Date Questions to Lead to a Serious Relationship

First dates sometimes feel like job interviews. Or worse, like we’re stuck talking about our favorite band and can’t seem to find any traction in a real conversation. I’ve been writing about love and dating for years, and have heard or lived every possible first date scenario.

First dates are about really getting to know someone and seeing if there is compatibility on an emotional, physical and mental level. You won’t be able to learn everything, but these questions cut to the heart of the matter and help you learn more at a deeper level. The key to these questions is to ask with an open mind, and with as little judgement as possible. The more open and curious you can be, the more open the other person can be with you. And this is where you begin to see your true compatibility.

What do you think/How do you feel about that?

Asking a person what they think or feel about a particular topic moves away from conversation about what they like and into a conversation about why. I ask this question all the time, even in friendships and networking relationships. And when I ask it, it is almost like I am met with a sigh of relief. Because what I’m really asking is “let me get to know you on a deeper level.” This is the level where people what to be known and understood.

What are you looking for?

I’ll be honest that this is the question I have the hardest time asking, and my clients seem to struggle too. We are so afraid of what the answer could be. We are afraid if the answers don’t line up that the relationship is over. But if the answers don’t line up, there is no potential for a relationship anyway and you deserve to spend your time with someone that can line up with you.

When you are brave enough to ask someone what they want and to also share what you want, then you are met with a beautiful reward of a satisfying relationship. No fear that he only wants you to get laid. Or not worrying that she wants to tie you down and have babies tomorrow. (those are silly generalizations, and yet they are unspoken fears that we have going into a date and carry throughout a relationship) You can’t get what you don’t ask for.

Where do you see yourself in 5 years?

I know this might sound a bit like an interview question. And yet, when I’m on a date I make it a fun game. I explain that I like to dream about my future and all the possibilities of what I want. And if I could have things all my way, there are certain things I’d like to have in my life. We know that we don’t always get things perfectly, but it’s fun to dream. If you are looking for a relationship with long term potential, it’s not only fun to dream together but it’s also fun to see if your ideal futures line up.

What are your dealbreakers?

A dealbreaker means that if this is present in a relationship, the relationship is over. This can come out at any time and immediately point the way to the door. So why wait until you are 5 dates in (or worse, 6 months or a year) and have real feelings involved? Most of us already know what our dealbreakers are. They are the things we must have in our life or things we absolutely cannot live with. Think back to what broke up your relationships in the past. There are no wrong answers here.

When was the last time you were tested?

Yeah I’m going there. And you don’t have to go there on a first date per se. But it’s a conversation you need to have before having sex. And someone told me forever ago that if you can’t talk about sex you probably shouldn’t be having it yet. We live in an age where we need to have this information before sharing our bodies with someone because it can have long lasting consequences.

This question can tell you a lot about a person very quickly. You can see how mature they are and how seriously they take their health and take responsibility for yours. It also lets them know this is something that you take seriously and is important to you. Having someone that is sex-positive and open to the conversation can be really sexy and show potential for a real future.

What do you hope to bring to a relationship?

I asked this (and the next question) on the first date with my current boyfriend, and I set him back on his heels. He’d never been asked anything like this, and it quickly became really fun. And we revisit these questions because as we grow sometimes these things change.

This is the equivalent to asking someone their strengths. Instead of saying “what are you good at in relationships?” you can ask someone about what they really love about being in relationships and what they hope to bring to the table.

All answers are welcome! I like to already know these answers and offer them first when I’m on a date. This helps to get the ball rolling.

What do you want from a relationship?

This is the equal reverse to the question above. It’s great to know what you’re bringing to the table in a relationship but you also have things you want from your partner. This is laying your expectations out on the table. I had a guy on a date tell me he was looking for a traditional housewife — someone to be home to clean and take care of the family. I think that’s wonderful that he wants that, but I know that’s not me. I know I want things outside of the house and I don’t have to compromise on that. So I could wish him well with no hard feelings because I would never be the person that he wants. I often have to tell my partner that my independence is really important to me, but in a relationship it’s interdependence. I like them in my life but I also like having my own safe space to retreat to and do my own thing. It’s ok to ask for what you want, and it’s also necessary.

Why are you still single?

I know this question strikes fear in the heart of long-time singles everywhere because we are used to our Great-Aunt Minnie asking some version of this question with extreme judgement. And on a date, maybe it feels like it’s also a bit judgemental. But it does not have to be a judgement that it’s wrong to be single. The way a person answers this question can reveal about who they are, how they move through life and how they see the world. You can look for potential red flags and let you know if this person is worth your time.

The goal with all of these questions is to really take a look under the hood of the car to see if it is something you are aligned with for spending a lot of time together and potentially building a life. There is a chance that you ask these questions and you learn you’re not a match. But you’ve only lost an hour or so instead of months trying to figure this out. And when you find someone that matches up with you, well, that’s just fabulous and seriously worth celebrating with a goodnight kiss.

How to Prepare to Create Connection

If you haven’t seen it yet, a woman is in her doctor’s office being asked routine questions about any pain she might be experiencing. With each question, the woman downplays her painful experiences, but her inner voice is arguing with her to speak up and tell the truth about how bad it really feels.  In the end, the woman says that it all feels awful.

I was listening to this ad for the hundredth time and an alarm bell went off. This is exactly what happened to me when I was dating all through my twenties and early thirties.

I remember so many of my dates where I was sitting across from a guy, and for whatever reason I lied to him about what I wanted, what I was looking for, or who I am. And every time I lied in order to be more of what I thought he wanted, my inner voice was quietly trying to advocate for what I really wanted. It would whisper “But you’re really looking for a guy that will treat you right and may be interested in marriage someday.” “You are nothing like this.” “He’s not that funny, why are you laughing?”  I twisted myself into a pretzel to try to become exactly what I thought he would want me to be. And then I wondered why I never felt a connection.
 
What I was missing all along was the truth. And I found it by asking myself what I wanted and who I wanted to be. I was preparing for my dates completely backwards.

In this video, I talk about ways to prepare for a date that have nothing to do with how you look on the outside.

https://youtu.be/bOlgXZwA9aE

No one teaches a person to ask these questions before dating. We say vague things like “Love yourself before you love someone else” but we never talk about what it takes to actually love yourself. Asking yourself questions like the ones in the video is the first step to knowing yourself better because you are actually being honest.

This is what I’m all about. Be honest, get clarity, then get what you really want. This is exactly the prep work you need to do to establish if there is a connection with the person across the dinner table from you. Because if you’re not honest and clear, there is too much standing in the way to allow for a connection.

What was your biggest takeaway from the video? What is one question you plan to ask yourself before going on a date?