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.

What's Holding You Back?

I used to really hate dating.

I just wanted to skip over all the awkward beginning parts and just get to the relationship as quickly as possible. I wanted to put an end to the uncomfortable first dates, the high hopes with a crash after the absence of a second date, and all the swiping. Ohhhhhh the swiping...

Your turn. Stop and think:   What is holding you back from love?
 

Here are my 3 limiting beliefs that held me back when I was looking for love…

1. I was holding on to my ex. 

Even though my past relationship was really dysfunctional, I knew what I was getting and I knew what to expect. I was so certain of his potential as a person that I was completely blind to the truth: he didn’t want a relationship with me. I really wanted things to be different, so I kept holding out hope that it would change. I dated other people, but in my head I compared them to my ex, always looking to see if they could stack up to what I imagined my ex to be.  There was one eye trying to figure out my future, and one eye focused on the past hoping he would come back. 

2. I was lying about what I wanted.

I wanted a real partnership of equals. But I was afraid if I said that it would scare away the person in front of me. So I compromised and said I wasn’t looking for anything serious, which felt truthful on some level. I didn’t want him to commit to a forever today. I mean, I barely knew the guy. But I was lying to myself because I spent years dating guys that weren’t serious about me or a future because I was too afraid to say what I really wanted because I was afraid I wouldn’t get it. Or worse. I would get a serious guy, and then I would have to actually show up as a partner, too. *gulp*

3. I believed that asking for help was selfish and it meant that something was really wrong with me. 

Don’t get it wrong- I would talk to anyone that would listen about my woes. Everyone in my circle knew my dating stories. We would laugh at the ridiculousness at it all or get frustrated together at the guy that couldn’t read my signals. As much fun as it is to share a story with a friend, it’s completely different to find an expert and get help with breaking my patterns that kept manifesting. I was dating unavailable men and pushing away the quality guys because they were “boring.” But I wasn’t getting the relationship I wanted until I started investing in myself and doing the deep inner work.

They say hindsight is always 20/20. We can see so clearly the steps that took us off the path. I can see pretty clearly where I was getting myself stuck, and I can see what I did differently in order to get a new results.

It’s time to do something different. Make a new choice. Break a rut. Take a step outside of the lines of the life you created for yourself. Ask for help when you normally would try to do it all alone.

I challenge you today to do something different today. Start small. Maybe take a new route home from work. And see how your perspective shifts. Leave a comment and tell me one small thing you will do differently today or tell me how one small change impacted your perspective. 

What To Say To The Voice That Says "You Should Be Further Along"

I am in my mid-thirties, and most of my friends are married (many also have kids). I have attended and been in more weddings than I care to count. And I have friends going through divorces before I’ve even had an engagement.

Most of the time I’m ok with this. I’m happy for my friends’ happiness and partnership. I’m inspired by them. But sometimes I beat myself up because it seems like they are so much farther down the path of life, and I’m left behind. I feel bad for not having my life all figured out. 

The persistent angry voice in my head is screaming, “What’s wrong with you?! Why aren’t you married yet?” 

Maybe you can relate. Maybe the voice in your head isn’t quite so angry, maybe it’s more despondent about being alone and lonely forever and you’re just a loser so accept and settle for this solo life. 

Whatever that voice in your head is telling you, I have the perfect retort. It surprised my inner critic into a moment of silence. 

“Calm the F’ down. Please and thank you.” 

I don’t curse all that much, so it was a bit of a surprise. The harshness worked in my favor. 

Here’s what’s really going on when that voice is getting really angry and pushy:

That voice is freaking out because it is worried about you and your survival. It’s worried that because your life doesn't look like everyone else’s, and to our inner caveman/woman being different = death. 

But it is only focusing on one small part of the world’s population. There are lots of people that do not have partners. Let’s use that logic to quiet the pushy, angry voice. 

Let your brain see new evidence. You are NOT alone. In fact, you are so far from being alone you might as well be in the middle of Grand Central Station surrounded by people just like you but you’re not even seeing them. Start looking for the evidence.

Here’s what to do: Challenge that inner voice to think of one person you know who is not in a couple. Think of one. (I’ll give you a hint- I’m not in a couple! Feel free to start with me.)

Once you think of one person that’s single, think of another one. Maybe Google badass single celebrities if you need some ideas. Give your inner voice lots of examples of other people that are living their life without being in a couple. 

Once you’ve collected evidence that you’re not alone, that voice quiets down a bit. It might say, “oh, I didn’t know that Mindy Kaling was still single. Damn, she’s awesome. And she’s a mom. OK, I see you, Mindy” 

Your brain can easily get stuck in compare and despair mode. When you are comparing your life to others and getting sad that it looks different, it brings down your entire day. And it takes you off track from getting what you really want. Instead of getting stuck there, take the offensive position. Take charge by telling the voice to Calm the F’ Down and take the back seat so you can drive this ship. 

You don’t have to listen to every little voice in your head. You’re the boss of you. You decide the direction that your life will take. 

So who would you rather listen to? The one telling you that you’re doing everything wrong? Or the badass that says, “This is how we’re going to live our life. No one else gets to decide what makes me happy. We’re going to make decisions. We know what we want, and we are going for it.”

I see that little bit of badass peeking through. ;) Let it out! You got this.

———

Did you find this blog post helpful? Do you want to increase the love in your life? It all starts with yourself, which is why I created a simple self love meditation. Claim yours here and get more love immediately.