Avoiding the Interview Trap on First Dates

“10 Things You Should Never Ask on First Dates”

In the articles you read with a title similar to this, you’d find these “taboo” questions that should never be uttered during the coveted, and sometimes elusive, first date. Now there are some questions in these articles that are quite obvious not to ask like, “Hey, who’s your hot friend?”

Ok, duh. If you’re asking these types of questions, you should probably punch yourself in the mouth. Repeatedly.

But the other, more pointed questions? Hell yes, I say ask away. 

These taboo questions of first dates: What are your beliefs and why do you believe them, do you want kids, is marriage something that you’re looking for, are you financially stable, do you know what you want or are you simply looking for a good time, where do you stand politically, what are your red flags in a relationship, etc.

These are perfect examples of some of the most important questions to ask on a first date.

I truly believe that if you have a clear idea of who you want your partner in crime to be in this life, why waste time with small talk and beat around the bush? Be blunt, be direct, and let it be known what you’re looking for. 

Why waste someone’s time?

When I first messaged Kacey, we got deep into the weeds with these questions right out of the gate, guns blazing. I was shocked at how quickly we were talking about our values, what we wanted in our futures, and the goals that we had for ourselves. We were just brutally honest with each other and never shied away from being authentic.

Kacey and I had a clear picture of what kind of partner we wanted. What a breath of fresh air that was. Being completely open and transparent right away was something I hadn’t dove into before. But I thought, fuck it. In my eyes, what was I to lose? If I can’t be me, then what’s the point of diving into another suffocating relationship? 

Can you imagine the depth of conversation that you could have by approaching dating this way instead of asking these boring questions: Oh hey, where do you work, where’d you go to college, what’s your favorite color, how’s the weather? 

These surface-level cover letter equivalent questions that you are bombarded with in interviews are my personal hell. Puke. Shoot me now. 

Now maybe I’m the weirdo for wanting deep and meaningful conversations. Some people aren’t as open, and I get that.

But those boring-ass questions don’t tell you anything about a person. Just frivolous, bullshit watercooler talk that you already have to suffer through when you’re at work. 

Old me used to think I had to bring these taboo questions up slowly over time while I was in the dating world because of similar articles as I mentioned above. Well, those first dates that turned into relationships didn’t last. Clearly. And for good reason.

We just weren’t compatible. Our values didn’t align. The way we thought wasn’t in sync. Our goals and aspirations weren’t even close. And they didn’t like bbq chicken pizza, an absolute deal breaker for me.

You could say the result of getting deep into the weeds of conversation right out of the gate could result in quite the opposite. Instead of an in-depth conversation, your date may shut you down entirely and walk out of the Applebees that you thought was a good idea, leaving you alone in that four-person booth having to eat the two plates of sizzlers you both ordered.

That may sting a bit.

But I say, good. It may seem like a loss at that moment, but that shows you clear as rain that they weren’t meant for you. 

And at the end of the day, aren’t you trying to find the one?

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