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Boss On A Leash

Kara Hart


1. Ali

2. Marc

3. Ali

4. Marc

5. Ali

6. Marc

7. Ali

8. Marc

9. Ali

10. Ali

11. Marc

12. Ali

13. Marc

14. Ali

15. Marc

16. Ali

17. Ali

18. Marc

19. Ali

20. Marc

21. Ali

22. Marc

23. Ali

24. Marc

25. Ali


I hate Valentine’s Day.

For the month of February, I’ve sworn off candy hearts, Hershey's kisses, and red roses. Above all else, I’m done with men. For all of 2021.


Fun fact about Valentine’s Day: The Romans used this wonderful little holiday as an excuse to whip women and sacrifice cute kittens. In 2021, men are still at their shenanigans. At least romance books are readily available. I haven’t sworn those off. Yet…

When I first arrived to my Seattle home, I thought everything would come prepackaged in a nice bow. The apartment I found to lease wasn’t charming, but it was quaint and very affordable. Meeting interesting people seemed to happen every weekend. I was within blocks of some of the best food, coffee, and beer in the country. I really thought I found my place.

But then I met Jack in the line to get my first pumpkin spiced latte of the season. It was a cold winter, much colder than last year’s, I was told. And despite the outside heaters, I was freezing my butt off. Jack was a gentleman. He offered me his coat.

I must’ve waited thirty-minutes for that over-flavored cup of coffee. It would’ve been worth it if I got there five minutes earlier. Instead, he asked me out.

Before I knew it, I was going on dates. He was sleeping over. We were… well, some things are better left unsaid. We were having fun.

When the first burst of endorphins hit, it felt like heaven. But when the tide rolled back, unanswered questions came into play. Arguments started. The smallest disagreements turned into major blow ups. I don’t even know what we were fighting so much about, but we deserved an Oscar for our performances.

We just blew up…

Another fun fact: People have been living in Seattle for over 4,000 years. No joke. But they’ve only been getting pumpkin spiced lattes for a few decades. I’m not sure if my trouble with men is related, but I wouldn’t doubt it. Weirder things have happened.

I’m not proud of our split, but these things happen. People break up all the time. I’ve always thought it’s how you handle those splits that defines your personality, rather than the number of heartbreaks you rack up. Still, it’s not very comforting knowing you’re heading into your mid-twenties, alone.

To top it off, my friends back in Chicago are all getting married. I’d rather not think about that now...

I moved to this gorgeous city to teach kids, not to date assholes, so when I wake up to the sound of my phone blowing up next to my ear, I jump to look at what it says.

Shadow Park Valley Day. Subject: Teaching Application

There are a lot of great schools in the city. I applied to them all. I also got rejected. They gave their reasoning, usually being that the staff was too full. Now, it’s February, and I’m at my wits end. If I don’t find something soon, I’ll have to go back to waiting tables.

Above all else, there is one school I want to teach at. Shadow Park Valley Day. It’s the most prestigious school, and it’s right outside the city in Sammamish, Washington. It’s only the most beautiful area outside of the city. Not only do they have the newest books, lesson plans, and computers, they pay their staff an arm and a leg.

Sometimes, I take my bike and ride around the neighborhoods there, fantasizing about what my life could be like someday. The forest surrounds the homes, and the air is quiet. Someday, I’ll get there. That’s what I keep telling myself.

I’ve been a substitute for the district since the beginning of the year. I know I’m getting a little ahead of myself, but I hope to teach there one day. Full time. Lord knows, I would give that job my all.

I adjust my eyes to the glowing phone display. With my email pulled open, I read the words as if they were from some holy scripture. My hands are shaking the screen, but I somehow feel okay about this. If I don’t get the job, I can always stay part time at the other schools. It’s not the holy grail, but I’ve lived poor my entire life.

Rain lightly patters against my windowpane, but the sun is peeking over the clouds. There is still some time until we hit that beautiful spring season, but this week has been gorgeous. Today is the kind of day that pulls you outside for a nice walk. However, as I read the email, I feel my calm pulled out from underneath my feet like a rug.

I read my sentence aloud. “Thank you so much for your application, Ali Greenwald. We are sorry to inform you that we are booked for the fall of 2021 and Spring of 2022, but we will retain your application for the next school season. All the luck in the world, Dr. Jordan Berman PHD.”

The school is perfect, so this is a blow. But just like all my past blows, I’ve gotten back on my feet. That includes my time with Jack.

Devastated as I am, there are other teaching positions. I have high hopes for my future. But the more time that passes, the more my brain searches for some extra dopamine. Instagram, Facebook, Tinder…

Oh, my.

There’s nothing for me in the modern dating world. I filter through hundreds of threads, reposts, and like-counts, until I return to my dreaded email account. It’s just a reality – I won’t be teaching at the charming red-brick private school of my dreams.

That’s okay. I’ve saved some money in case I have a really bad month. It’s not much, but it’ll have to do. I’ll come in whenever they need me to, and I’ll keep my eyes peeled

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