#2: The Difference Between Care Free and Careless

And we’re back! Happy Friday, everyone. I gotta say, it felt cathartic last week to send some writing out into the world, so I hope you enjoyed it even half as much as I did. One of the first questions I received when I opened my inbox was about romance, which is fair. I’ve gone through some trial and a lot of error with that, an unsettling amount of it being on the record.

When Amir and I started our podcast I was in my mid twenties, single, and living in New York. Listeners may remember I followed my impulses without thinking about the consequences. And to be honest, it was awesome. But not all the time. The ping ponging effect of never knowing what I wanted, and always wanting different things, often left me feeling emotionally hungover. Usually this was on top of an actual hangover, which wasn’t ideal.

One morning just like that, I was picking up coffee at Starbucks (another one of my depraved tendencies) and as I sat feeling empty in my car, I suddenly gave myself a pep talk. I later learned I had stumbled upon the idea of a morning affirmation. I kept it up. Most days, I said some version of the same thing- that I was a tree, reaching for light while planting my roots deep into the earth. I told myself that I was looking for solidity and grace, and that I wanted to fill my life with people who wanted the same. Most nights, I filled my life with Big Buck Hunter and a bad DJ.

As I said, there was a lot of error.

Let’s listen to a song, my morning anthem for this period of my life, as we settle into this week’s column.

Hey Jake,

I’m a 22 year old environmental science student in Canada. Lately I’ve been reflecting on the way I approach romance, and I think I’m doing something wrong.

I’m currently single. Romance and attraction is a big part of my life. I always have multiple crushes, and I’m always flirting. Not to brag, but I’m actually pretty good at it because I’m not afraid to be confident and outspoken, which I think people find attractive.

Issue is, whenever I feel like somebody I was into is interested in me… I lose interest. I don’t know why. It makes me feel awful, because I feel like I must be confusing these girls. I don’t want to be mister mixed signals anymore, but at the same time, I can’t figure out a way to control these emotions.

Any advice?

Dear Mr. Mixed Signals,

Good work on developing this conscience about 6 years earlier than me. It is thrilling to have a crush. I don’t think you can fully control that emotion, especially at 22. But I like your instinct to understand it. Because while it’s fair to seek feelings that are wild and new, it’s not fair to play with anyone’s heart in the process. It took me years to learn all this, but let’s see if I can explain it in a single newsletter…

The first person you need to talk to is yourself. If you can’t be honest there, you won’t be able to be honest with anyone else either. So, let’s think, what are you actually seeking? For me, I was looking for validation. How do I know? Because I still look for it now. I sought it out this morning when I held the door open for an old woman at Paragon Sports. She smiled and said, “They should give you a job as the greeter,” and I said, “I’d do this for free.” We laughed, and I swear to you I still felt the rush, the spark of human connection and warmth, and we didn’t even have to make out. Flirting has many forms, and you don’t need to follow every flirtation to its conclusion.

That said, maybe you don’t need the validation. You could have a fear of intimacy. That’s a fun one, I had that one too! Maybe you realize that letting things progress with a crush means opening up. And opening up means being vulnerable, which means you can get hurt. While we’re chucking things at the wall, let’s also consider this: hey, you are 22, and maybe you’re just seeking casual relationships and exploring the dating pool. That’s fine, and also, as I previously stated, awesome.

Remember, these are just options. Like a weird little multiple choice quiz where all the answers can be correct, even d. None of the above. No matter what, the point is that if you are feeling this way, it’s a good idea to hit pause. To look inward and try to get to some semblance of an answer. Once you have a clearer picture of what is driving you, the signals you’re sending will get cleared up as well.

I hope this only felt like a gentle wake up call, like a Grande sweetened iced coffee with a splash of breve. You are young and this is the time when everyone around you is figuring out the exact same thing. So don’t feel like it’s all on you, either. You have signals to receive too, you know. Embrace the chaos, but never at anyone’s expense. And when things get too messy, remember that you are a tree, reaching for light while planting roots deep into the earth.

Thank you for reading everyone! We will be back next week. In the meantime, you can click the button below to recommend this newsletter. That would be sick.

Want a Jake Take on anything going on in your life? Just send an email to just.contact.jake@gmail.com