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.

Why All That Pressure?

Have you found yourself feeling really nervous before a date? Stressing out about wearing the perfect outfit, asking the right questions, and acting the right way? 

I think we've all been there. Those pre-date jitters. On one level, they are fun and exciting but on another level they are terrifying. But what are those jitters really about? 

If we take a step back and look at why we're feeling nervous, we realize we are feeling that way because we have an expectation. We are putting a lot of pressure on this one interaction because we are worried it's our only chance at a life-long happy partnership.

When I say it like that it looks pretty silly, right? All this expectation and pressure on just one interaction? Seems ridiculous but we do it ALL the time. 

It's the subject of today's video, and I encourage you to check it out here.

As a side note, I was preparing the email for this week and I realized how strongly this topic parallels to so many other areas of our lives where we create unnecessary pressure. We're trying to make a diamond, when what we really want is a snowflake. Even if you're not dating, I encourage you to watch the video because there might be something useful for you, too. 

Look, I know it can be tough out there in the dating world. it feels like it takes forever to find a somewhat decent guy to actually spend time with on a Thursday night (let alone a guy that's worthy of a weekend date). And then, when we finally get to the date, it seems like a big let down.

I want to help make dating a bit easier for you. That's why I'm doing a free webinar, Why It's Hard to Get a Guy (And What You Can Do About It) tomorrow March 14 at 1pm Eastern Time. 

I'm going to be addressing some of today's issues that are making it harder now to find a guy, plus I'm going to be offering some guidance to shift how women approach the dating landscape to make it so much easier. Everything I teach has been tested and honed by yours truly, and I can't wait to share it! 

You can sign up to attend the free webinar here: https://sarahcurnoles.lpages.co/why-its-hard-webinar

I hope you will join me tomorrow! (and even if you can't be there live, I will be sending a recording afterwards)
 

First Dates Can Be Rough. Take It From Me.

I was the queen of the first date. For most of my twenties, I was great at getting a guy to ask me out for the first date, but I never understood why there wasn’t a second.
 
I’d go out. Engage in witty banter. I would wear my best outfit.  We’d talk about work and our friends and families and what we were passionate about. Usually, there was a goodnight kiss. (And I don’t mean to brag, but I’m a great kisser. I am 100% confident in my kissing abilities.)
 
When he didn’t ask me out for the next date, I felt distraught. I tried so hard to be the person he wanted me to be. I tried to be what I thought he was looking for: the perfect blend of sexy, independent, cute, funny, smart, accomplished, and nurturing.
 
I couldn’t figure it out.
 
All these years later, it’s clear to me what I was doing wrong. I made the same mistake a lot of people make on a date by staying on the surface level of connection. We talked about what we had in common, not about the topics that would actually make a difference. In this week’s video, I talk about how to take that surface level connection and turn it into something that will go deeper and will foster a better connection. It will also help you evaluate if you like the person across from you, and if your values line up.  
 
Check out the video here.

I felt really frustrated when I was trying to figure out why all my dates seemed to fail and never get a relationship off the ground. It reminds me of when my iPhone wouldn’t turn on, so I panicked and took my iPhone to the Genius Bar. I was freaking out. And my Genius was so calm, she methodically went through a checklist of options to fix my phone. I commented “You’re lucky to work here. I bet when this happens to you, you’re cool as a cucumber because you know it can be fixed.” And she said something very wise to me:
 
“No, I’m a mess! When it’s your problem, you can’t see the answer.”
 
It is always going to be easier for a person outside of the situation to be able to breathe, take a look around, and see the possibilities for solutions. We can cultivate this, and that’s why I teach. Because I want to empower women to be their own best guide, and so that they have somewhere to turn when they need someone on the outside to help.
 
I’m going to be offering a free webinar about recognizing and solving one of the biggest dating problems: Why is it so hard to get a guy? In this webinar, I dissect the problem that many women are having with dating right now- there are so many options, but the quality seems to be lacking.
 
And I’m not going to show you a problem without giving you an answer, of course! I will then help women see what they can do to answer the question and actually start finding great guys.

If you’re a single woman who is dating and wants to understand this better, I hope you will join me on Wednesday March 14 at 1pm EST for my free webinar called Why It’s Hard to Get a Guy (And What You Can Do About It). You can register by clicking here.
 
Even if you can’t be there live, only people that are registered will receive the recorded playback. 
 
I’m already jumping out of my seat with all the juicy information I will be delivering to you. I just can’t wait!