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Onward, Ho

Updated: Sep 14, 2022

Today I am celebrating my 32nd birthday. To this day, I have somehow succeeded as a thriving artist in New York City for 9 years; I have never missed a rent payment, Aaron Carter kissed me once, and I’ve afforded exactly 2 treatments of Botox. If that isn't success WHAT IS.

Obviously that sentence does not even begin to encapsulate how much I have “accomplished” in the last near decade in New York City. I have done so so much more, which you can read all the hell over this blog, but specifically here, here, and here.

There are nights like this past Friday that remind me just how far I really have come in my From Missouri to Manhattan: A True Glow Up journey.

After ending a relationship a few months ago, I have decided that although I still miss this person, I have got to move on and make myself available at some point. So why not get back out there, be open, and have a little fun? Perhaps I’m not "fully moved on", but I also believe that, by a certain point in post-relationship recovery, finding connection with others can be very healthy for furthering the recovery. As a friend of mine put it recently, "Like a little palate cleanser." Anyway, I went on a date.

It was an absolutely horrible date.


Did this dude just say he’d rather me ask about his exes than how he did something really cool…get into multiple Ivy Leagues? WTF.


We met on the Upper West Side, although I really don’t like the Upper West Side -- except for its nostalgia -- which was a good setting for this particular experience. I understand the "You've Got Mail" charm of this neighborhood, but to me it’s just crusty. After all, it is the first neighborhood I called home, where I spent my early twenties – the sloppiest, messiest, everyone here is so old - years in New York City. The whole time I lived there, I couldn’t afford any of its charm – restaurants, boutiques, Harry's Shoes – so I guess I just don’t get it. But again, for this experience ie remembering 22 year old me sitting at that same bar on a date, having no idea who I was or what I was doing, to contrast against that evening’s goings on, it was perfect.

Let's be very clear (because I'm really fucking sick of recent/ongoing unfounded accusations): MY WRITING IS NOT ABOUT PUTTING MEN IN MY LIFE ON BLAST. It is about sharing stories from my life and what I learned, with the intention to help others maybe navigate their own. Therefore, I will share the circumstances and events as they occurred through my lens, which will involve other people. That is part of storytelling. That being said, there is a difference between transparency and privacy, and I think the details I share publicly (at least in the last 2-3 years of my writing) show I know the difference.

Also keep in mind, this is all subjective. The man with whom I spent this evening is not indisputably terrible. Another woman could have had a great time with this un-ironically misogynistic man who, although in therapy, clearly hasn’t worked through all the (IMO) unhealthy ways he defines his masculinity I.E. Ivy League education, lots of money, beautiful women, lots of sex with beautiful women. A man who kept trying to detour our conversation to sex, but then would never let me finish (foreshadowing amiright) a thought about my sexual journey/history because HELLO I HAVE A LOT TO SAY ABOUT THIS. A man who mocked me when I said it’s very important for the person I’m with to find my passions — writing, acting, filmmaking – sexy. That is a non-negotiable to me feeling seen as a person, and therefore, comfy to get physically intimate. A man who told me our conversation felt like an interrogation.

But I am not another woman, I am me. And to me, he totally sucked.

Towards the end of the date, he expressed his frustration at me.

“I just don’t understand how my financial aid to *insert Ivy League school* is relevant to how we will connect romantically in our relationship. Shouldn’t you be like, asking about my previous relationships since we are on a date?”

Did this dude just say he’d rather me ask about his exes than how he did something really cool -- get into multiple Ivy Leagues -- ??? WTF. Also okay, yes please tell me exactly what I "should" be saying to ensure you have a good time, Commander.


If I were a previous version of myself – the 22 year old me sitting at the bar with Tindr date #42, did I just make him uncomfortable? more shots please! – this man’s commenting on how I conduct conversation would have left me feeling insecure and questioning myself


“I didn’t ask about your financial aid.” I replied, not really masking how offended I was that he found my general getting-to-know-you questions to be interrogative. “I asked why this Ivy League over that and that Ivy League. I asked why grad school at all. I’m just trying to get to know you as a person. I don’t think you can even entertain a romantic attraction if you don’t actually know a person. Are you saying you’d rather I ask about your exes on a first date than why you chose to go to grad school?”

“I dunno, I just feel like you already know more about me than some of my closest friends.” He said exasperated. “Can’t you just tell me what you’re looking for? Because it sounds to me like you don’t really know.”

So. Much. YIKES.

If I were a previous version of myself – the 22 year old me sitting at the bar with Tindr date #42, did I just make him uncomfortable? more shots please! – this man’s commenting on how I conduct conversation would have left me feeling insecure and questioning myself. There you go again, MJ! Being too much! Stop being TOO MUCH for this clearly very strong, successful MAN! You want his approval, don't you???!!!!

But I’m not a previous, insecure version of myself, so instead I thought Wow, okay. Clear incompatibilities here if this guy thinks me asking questions about his life, his choices that lead him to New York, if he wants to stay here long term, etc… are more private than his romantic and sexual relationship details. Also says a lot about how he interacts in the world. His friends don’t know why he chose the grad school he chose? His friends don’t know why he’s choosing his certain profession? Men without close friends with whom they actually discuss life with are not my audience. Get some friends so you don’t beat your wife, homie.

Oh and then the part where he commented on my not knowing what I want? LOL. Because I’m not flattered by your constant advancements throughout the night? How not self-aware of a dude do you have to be to not realize you’re behaving like a wounded puppy because I’m not jerking off your ego, and instead trying to have an intellectual conversation? Anyway, another round for me. You can leave, sir.

I still answered his question.

“I’m looking for…honestly, I’m just ready to not get my heart broken again. I want someone who wants to and can hold my heart. Fully.”

He also found that very stupid, I guess. Because he laughed at it. Another thing that maybe in the past would have made me insecure. Was that too Enneagram four-y of me? Too cliche sounding?


I would not cry about exes in front of this unqualified-for-this-level-of-MJ - vulnerability- experiencing asstwat


No, you asshole! It was fucking honest and beautiful. I am honest and beautiful!

“Who broke your heart? He replied through his insulting chuckles “And how?”

And then, at the worst possible time ever, tears started to well up in my eyes.

No no no NOT THIS. I cannot have a cry, sitting across from this dickwad on a first dating app date because I am very suddenly overwhelmed with emotion thinking of all the men who have catalyzed heartbreak in my life.

If this very untimely arrival of water from my eyeballs is not proof that your girl really knows how to feel her feelings and could not stifle them if she tried, I don’t know what is. Please be proud, therapist + Amy Young.

But still, I would not cry about exes in front of this unqualified-for-this-level-of-MJ - vulnerability- experiencing asstwat, so I pinched every muscle in my face (not visibility, ofc. Cuz Botox) to hold them in. I started to speak and the tears were almossttttt falling off the crest of my bottom eyelashes, so I stopped talking immediately, looked down, muttered “Ummm” a lot until he finally started mansplaining heartbreak.

I found myself thanking God for a mansplain in that moment. A truly once in a lifetime occurrence.

Once the tears were back in their ducts where they fucking belonged, goddamnit, I got angry at his very stupid explanation of how I should experience heartbreak. I cut him off.

“Look, I know nothing is guaranteed. Obviously. I know people look to relationships for false security and safety. But I think the commitment to knowing a life together is better than life apart…that’s what I want.”

We got the bill, I paid for my half* because dudes like him are never generous “just because” (and it was very clear he would not be getting laid), and we parted ways.

*A quick diatribe about paying for dates and being a feminist. I almost always make less money than the dudes with whom I am going out. Especially this type of guy, who is undoubtedly making $500K/year or more. So, for me to pay for my $50 half of the bill, when you make the amount of money I’ve made in the last maybe 10 years is fine, but doesn’t show the kind of generosity I appreciate in a person. If you make less than me (which has happened also in my dating experiences!), then so long as I see that generosity manifested elsewhere. -- Leaving me a surprise bottle of wine at home, making dinner for us, planning a picnic, asking for my coffee order so you know what to get me and then surprise me with it everytime you go get coffee -- it's all good! Little things like this show a thoughtfulness and generosity that doesn’t have to be expressed financially. I also understand that dating app first dates are different, because you’re meeting someone for the first time, so you don’t even really know them well enough/like them at all to justify dropping lots of money on them. But again, if you’re a lawyer or work for a hedge fund, what is $100 to you is WAY LESS than $100 to me, an actor/writer/babysitter. It’s. About. Generosity. Also, if you don’t want to risk spending that much money on a first date, suggest things like walks and coffee or sushi in the park or Citibikes. I often suggest these activities for first dating app dates just to avoid this awkwardness. Okay, back to your (un)paid programming.

In my previous years, I would be devastated about this date and how poorly it went, making it mean I will never find love and picking apart every detail of the evening to reinforce I am simply "too much." I would make it mean all men are dumb dumbs and this finding love thing is so impossible and why am I straight ugh (all very valid thoughts and feelings, btw).

Instead, I walked away from that date being grateful it was over, the drinks were happy hour prices, and it’s only 8:30 so I can still enjoy some tea and talk to my bestie when I get home! I also walked away knowing, because I've been at this dating as an adult thing for awhile, some dates are just going to suck. Not every experience can be an amazing one. Not every experience can even be a good one. That is just how this dating thing goes. Onward, ho (see what I did there).

Still, this morning, I found myself reflecting on the question posed that, at 32 years old, prompted a near-tear-experience in-a-very-crowded-loud-bar-sitting-next-to-20-something's-playing-Jenga- dating-app- flop.

Who broke my heart? And how?

Stay Tuned for part 2 :)


I do not have a patreon, and I’m not going to start one lol But if you love reading my blog, enjoy my IG content, and want to support me in some small way, you can always donate via venmo (@mattiejo-cowsert) or ask me for my Amazon wishlist link, which includes very important things like toilet paper. Oh and also buy my book when it comes out plz and ty. ;)



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