What is your biggest mistake or regret?
11.06.2025 01:28
“Babysitting? You told me I was gonna be your graphic designer for the performing arts studio.”
Most of my money in my checking account, gone, from all the shit I've been having to buy, from the black clothes I had to get for the stage play, from the new bedsheets and blanket I had to get for the broken air mattress just so I wouldn't freeze at night, for the frozen dinners so that I wouldn't starve when we got home.
Mary had to move back to Stuart, and to the best of my knowledge, she has never gotten back on her feet again. She's still alone, still doesn't have her kids, still living an unstable life, and is still refusing to get help for her clearly unwell mental state.
When I was working, I had a tradition of taking out some money every paycheck and putting it in a box as a nest egg. It was something physical I didn't want to touch, a physical representation of how hard I was working to one day afford a car, a home, a life outside of the mess I kept finding myself in.
Then slap yourself in the face for the following thought process.
Something that would actually make it reasonable to be snooping around your boss’s goddamn bedroom, I was sure.
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$2600, gone.
I gotta get away from her, and she's apparently offering me a car now.
She proceeded to self destruct.
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My heart was racing, could this be it? My big break? My chance at making an income and a name for myself?
“Then why didn't you?! I made you a logo, I made you a website, I went through twenty thousand fucking revisions for your picky fucking ass and you throw $50 my way and you think that covers it? You're a horrible person, Mary! No wonder Aaron left your ass!”
I have never regretted a series of decisions more in my entire life. I felt horrible, not just for myself and the bad situation I was in, but for how worried all my family members were, how none of them were in any position to help me and how hopeless we all collectively felt.
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We never got a hit, and she never put anymore effort into the endeavor. It was dead within the week.
“To the dog park!”
I rush inside and start packing my things. I wasn't sure of where I was gonna go or what I was gonna do, I just knew I needed to get the fuck out of there.
The moment the money changed hands, things got even worse.
For the next ten hours I babysat three random kids while Mary stalked Aaron's Facebook, intermittently turning the phone in my direction and saying “Isn't this weird? He only wore this shirt on dates with me, he must be going on a date tonight, don't you think?”
And I paid Mary for her car.
I had her drop me off at a McDonald's.
She had previously been a performing arts instructor, and was currently a divorcee with two kids she was fighting for custody of.
“Nope!”
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“PSL?”
Mary moved here to stalk Aaron.
“To work, silly! We're gonna be babysitting like I told you.”
“Yeah, we haven't had any classes yet so we need to make some money in the meantime. Also at night you're gonna be helping me with my church performance of Annie okay?”
“The milk stain?”
She had an ex-boyfriend, Aaron, who she never stopped talking about.
I should have taken this as a sign from God himself to say no and stay put.
“There's plenty more where that came from once the studio is up and running!”
Her performance of Annie bombed due to a lack of planning and too much of a focus on what didn't matter, that being Aaron. My not being there also meant she had to do my job as well as direct the play. All of this showed just what kind of teacher she would be for the students in her performing arts studio, and the few kids who actually had been enrolled under her, but had yet to take classes because she was a disorganized mess and never prepared any, were pulled out.
What should I do if I love a girl and she apparently doesn't love me?
That night I asked her when she'd be giving me the keys to the car.
I fell in love with it, and I felt so, so hopeful.
It somehow gets even worse.
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For the next eight hours I worked out a way to get back home.
“No, this is from a man, this is spunk.”
Eventually, after several hours, we both calmed down.
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This crazy woman is just getting worse the longer I stay with her. I don't know what's wrong with her but I know she's not mentally well.
Where she buys herself a nice new fancy phone.
“No. It's from Aaron. She's been fucking Aaron.”
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No matter what we were talking about, no matter what we were doing or where we were or whether or not it was relevant, she'd find a way to bring up Aaron.
“You don't get it! You don't get it because you've never been in love! I need him, Sully, please help me!”
Now, I want you to put yourself in my shoes for a moment.
“Where?”
I have no idea how Mary managed to convince him to come over- oh no wait, yes I do.
He picked me up and got me back safe and sound.
Is it okay for a wife who comes home from a date to tell her husband what she did?
If I got the car, I could take off. I could leave. I could go home, go anywhere, hell, I could live in the car for a bit if it came down to it.
However the hell she thought that would work!
This is a long one so buckle in.
“You see that?”
“Wait, let's get a drink, Sully don't you wanna go get a drink with Aaron?”
My stupid fucking ass says “How much?”
My life since then has been relatively calm. Mary's, to my knowledge, has not been.
“I'm making great money down here, I get like $1000 a week babysitting for this rich bitch in Summerland, she's like a dentist or something. My rent is only $1000 a month so I wanna take that expendable income and do something amazing with it, you in?”
I messaged my grandpa, I told him where my stash of money was.
I was so fucking overwhelmed by all the shit she was putting me through, how every day got a little bit worse and now she was fully expecting me to seduce her ex so that he'd sleep with her!
Mary finds Aaron and starts chatting him up, and you could tell from twenty feet away that the dude wanted her to leave him alone and let him play with his dog. She somehow convinces him to come over and talk to me, and she seems really insistent on finding things we both liked for us to talk about.
“Yeah but she's a friend of mine, I don't wanna piss her off.”
“Where's all my money, Mary? You took my money for your car, then you don't give me the car and you spend it all on a new fucking phone for yourself! You're a selfish bitch, you never even paid me for my work!”
All because I wanted freedom.
At a completely made up, completely impossible scenario.
“$50? I thought we agreed on a lot more?”
“Hey Sully, guess where I'm living right now!”
I'll always remember that man as an angel, because he really was an angel for me.
“I'm in the keys! I'm living in the keys!”
“Uh, in Stuart?”
I had a rockstar ex-boyfriend who frequently toured in the Keys, and I was always upset when he'd refuse to bring me along.
I didn't.
She's standing in the doorway of her boss's bedroom.
She comes to me and says, “Sully, I need you to come look at something.”
“Oh come on, one little drink won't hurt you!”
I met up with Mary at the Greyhound station and she picked me up, took me out to eat, and then brought me grocery shopping. We headed to her “apartment,” and all my hope very, very quickly began to fade.
“It's milk, Mary.”
“Maybe you could get Sully a job tattooing around here, you know lots of people don't you?”
I told her no.
“Absolutely not!”
I tell her no, that I'm done with this shit. Aaron goes in and I leave, I go to the gym bathroom with my phone this time, and I cry.
I know what “spunk” looks like.
I had him transfer the money to my account.
“Do they even know each other?”
Despite every red flag in the world getting flashed in my face right then, my dumb ass said yes.
My god, it was stunning. Water so blue you could paint with it, the sky seemed to stretch on and on for eons, endlessly fading into a horizon of gentle ocean waves.
“I guess that depends.”
“Or its nighttime and he just wants to go home?”
“How much you got?”
I felt broken.
With my hard earned cash.
“But if she hasn't paid you then she has the entire building for free!”
I agreed to help, and she put me to work immediately. I made a logo for her, fliers, business cards, posters, pamphlets, everything she could conjure up needing 20 different versions of, I did it for her. Opening night was in less than a month, she was having a big party to celebrate and generate buzz for the studio, so I was rushing not only to get everything together, but paying out of my own pocket to have it printed at office stores near her as well.
Well to stalk her ex-boyfriend Aaron of course!
I cried in the corner.
Next day, the climax.
He comes over, and at this point I have no idea what she's told him.
When opening night came and went and the time came for my payment, I was expecting at least a grand. I did a shit ton of work for her and went out of my way to ensure she had everything she needed.
She wanted to start a cleaning business with me, so we went to Dollar Tree and bought a shit ton of cleaning supplies. We probably dropped $50 each on sponges, wipes, Windex, grime remover, squeegees, etc. I was skilled in graphic design and made us a logo and a Facebook page.
“But you got it for free from the church, you said that-”
She paid me back, of course, but I still found it weird that she couldn't figure out how to do that part herself.
I don't say anything.
It was one big office space, that she wasn't supposed to be living in, that she had converted into a makeshift home for herself.
In the Keys of all places?
As for me, I'm doing pretty good for myself.
This woman had memorized my passcode by looking over my shoulder when I was unaware, and was stealing my identity so that she could see her ex-boyfriend again.
“By the way, in the mornings I'm renting this place to a yoga instructor so we have to be out by 5AM.”
$2600.
“Nope!”
Nearly a year later, in September of 2019, I get a call from Mary.
Then she has the fucking GALL TO SAY THIS, “Do you think I should be charging the yoga teacher for using the studio?”
I leave the room and return to the kids.
I was so desperate to move out of my grandpa's place, I just lost my job, just broke up with my crazy girlfriend, and just had my last comic book I wrote flop like a dying fish. I was in need of a break, and desperate people tend to favor rose tinted glasses.
5 years ago I was abandoned on an island after being coerced into living in an office building with a stalker who wanted me to sleep with her boyfriend so she could have him back in her life.
So we go to another bar.
For a shitty van.
She runs up to me, frantically crying, saying, “Please, please, I need you to call him, I need you to get him back over here, please!”
I follow her into the room and she points at, what is very clearly, a milk stain.
She threw things around and tried to break shit and yelled at me to stop.
Now, why on earth would two people without a dog be heading to a dog park at 6PM?
For another five fucking hours I babysat more random kids, ran stage props back and forth, made sure the kids didn't hurt themselves, got drinks and snacks together for the kids, ran scripts back and forth, loaded props back into her van, helped make props, fixed props, glued broken shit back together, etc.
She said she'd come up and get me and bring me back down same day, so I said my goodbyes to my grandpa, packed up my bags, and waited for her to say she was on the way.
Another bar fucking Aaron just so happened to be at.
“I bet he's meeting a girl. Probably has a date with her.”
This was not spunk.
The following morning she asked me if I would stay.
I slept on an air mattress with a visible hole in the side of it that night, on a cold office floor with an AC unit that she had lost the remote for so it was constantly set at 60 degrees. I had nothing but a little sheet to cover me.
Now, there was one thing I didn't bring with me before I left. My savings.
Next day, similar dig.
“I do, I been saving up. But I'd be willing to sell my current one to you if you want.”
My life is no longer so adventurous. No more rock stars, no more crazy girlfriends, no more trusting people I shouldn't be trusting. I listen to my gut now, I leave bad situations before they can get worse, I block people when they come at me with fanciful dreams and too-good-to-be-true exclamations, and I'm no longer a fan of rose colored glasses.
It was my hope box.
She slammed the front door and said I was doing it. She stomped around and made a ton of noise and said I was doing it, and I needed to be quiet so the security guard at the gym doesn't call the police.
All the while we had a screaming match, and I've never been more pissed off at anyone in my life than I was at her that night.
After dragging me to a bar so she can drink away her sorrows while stalking Aaron's every last move on Facebook all night, finally, she takes me home.
I was so terrified that I'd be left to fend for myself all night, that I'd have to panhandle for money or just sit there and wait for one of my family members to finally get the means together to come get me.
“Yeah, they're cool.”
Furious.
She lost her job as a babysitter and was found to be living illegally in her office, and was consequently kicked out. I bet that'll look real nice the next time she tries to get custody of her boys.
I was exhausted. I wanted to go home and sleep but no, this bitch wanted to go fucking party.
The car meant freedom.
Aaron moved halfway across the country and told me he was getting a restraining order against her. We messaged a few times after this mess was over, and I apologized for everything she sent him from my phone. He understood completely, and held nothing against me. I told him if he needed me as a witness for anything legal against her, I'd be more than happy to help him.
“Well we had agreed on $100 a day but she hasn't paid me yet, and I need the money so I don't wanna be mean.”
“Sully here wants to become a tattoo artist, you love tattoos don't you Aaron?”
Turns out, Aaron lived in the Keys now. Aaron moved here to get away from Mary.
I had been expecting to be paid for all the work I was putting in for this absolute bitch, and now she left me with nothing.
“5AM? Where the hell are we gonna go at 5AM?”
“Oh come on, I just need him around long enough to convince him to stay with me, please?”
I just so happened to get the last bus to Homestead, and just so happened to have a family friend who was working in Homestead and lived near my Grandpa.
Now, Mary was down on her luck, I knew that. It was obvious. And she was a sweetheart when you first got to know her. A nearby church donated a van to her, so she'd give me rides, take me out to eat when she had some extra money together, we'd sit in the park and tell each other our dreams and make grand plans for how our futures would pan out.
I look at her face, and I felt like a deer locking eyes with a mountain lion.
He leaves, and Mary is erratic as hell over it.
She starts walking around the house, investigating shit. I don't know what she's doing, I'm busy taking care of three damn babies and listening to fucking CoCoMelon on a loop.
She was trying to frame me.
Except this bitch has the gall to say, “You know, I really need a new car.”
“No!”
Now I'm thinking, did she find something bad? Like, evidence that the kids are being abused or something bad? Did she find something illegal? Something unsafe?
And now Mary was down there, living it up according to her.
And she was on his Facebook. Again.
She says “Honey, you're not getting my car for $2600.”
I accepted that I literally had no choice but to stay there at least one more night.
“Nevermind that right now,” she's staring at her phone, keys in her hand, far from looking like she was about to let me settle in for the night, “come with me, I wanna take you somewhere.”
I moved here because I was a fucking idiot.
Same dig in the morning. Wake up 5AM, go babysit a bunch of kids I'm not related to, at this point I don't even know if she'll be paying me for doing this.
It was not an apartment.
“I do. Listen, I gotta go-”
I get on the phone with my bank and try telling them that I need the last transactions to her to be reversed, and they basically say I'm up shit creek without a paddle, because there's nothing they can do.
She was deadly fucking serious.
“They probably do! They both know me so they probably know each other!”
“But I thought you said-”
“No, I know him. He's probably fucking some girl tonight. Come on, I need a drink.”
Because every time I was asleep, or in the bathroom next door, or in any other situation in which I didn't have my phone by my side,
$50 has hit your account!
The following morning she woke me up at 5AM, and rushed me out the door.
I suddenly hear screaming outside, both a man and a woman. I run out, and she's chasing his car as he's driving away.
I had met Mary about a year prior to this incident back when we were both homeless.
“I'm getting back into performing arts, I'm starting my own studio! And I know you're skilled in that graphic design stuff so I knew I'd have to ask you if you'd help, I'll pay you of course!”
How the hell she could afford that, I had no clue. Florida is notoriously expensive, and the party islands were no exception as far as I was aware.
Eventually, we drifted apart as friends. She got a place, and I moved back in with my restrictive grandfather. He was kind for taking me in and forgiving me for leaving the cult that in a roundabout way left me homeless in the first place, but he worked at every turn to get me to come back, telling me things were going bad for me because I had disappointed Jehovah and lost faith in him, and that I needed to return if I wanted things to get better for myself.
“Listen, forget that. We're about to make bank here and I really need you on site, can you come live with me? I won't charge you! You'll exclusively be my graphic designer, we're gonna need a lot more work done!”
We had to pack up all evidence that we were living there in this big cardboard box in the corner, and we covered it with a sheet, so that when the yoga instructor came with her class she didn't see air mattresses and clothing everywhere.
That wasn't happening, but he still let me stay regardless. It was my goal to get a job and get out ASAP.
“Please, you made some fliers! I could make fliers!”
Mary was using it to message Aaron, pretending to be me, pretending I was interested in him, then deleting the messages so that I wouldn't know.
Good for him though, just as we were pulling in he was leaving.
“No, I'm done with this. You're insane, he doesn't fucking want you, get it through your fucking head and leave him alone!”
I walked out.
“No, I don't drink anymore, I wanna go home.”
There's three kids in this house, the youngest is a few months old and the middle one is a toddler. A milk stain is more than expected.
“You got the money for one?”
“You aren't getting a whole ass van for $2600. Don't be ridiculous. I expect at least $10,000 more, I'll be taking it out of what I owe you for babysitting every week.”
She sent me the money, I got myself an Uber to a Brightline, and from a Brightline to a Greyhound in Miami. Back then Brightline had $5 rides for new customers, so getting down there was surprisingly easy, and from the Greyhound I headed to the Florida Keys.
“I really gotta go, Mary. Nice meeting you, Sully.”
Immediately, she packs up the kids in the car and takes us all to a phone store.
After the mother came home and we were free to go, Mary took me to the church where she was putting on a performance of Annie, for free, as publicity for her performing arts studio. They were still in rehearsals but she expected me to also be on staff for the real play in a few days.
That moment in McDonald's was in itself an adventure, but I did, eventually, make it back home safe and sound.
I was immensely uncomfortable the entire night, regretting every decision I had made earlier that day, cursing myself for not listening to my gut, but still somehow hoping this would all work out.
“Can you just act kinda flirty towards him? I want him to think he's gonna get with you.”
I had about $2600 in there. I left it in my closet, because I didn't want to risk anything happening to it until I was situated in the keys.
I woke up 6AM with the expectation that Mary would be arriving within the hour, as we had planned the night before. She texted me, and said, hey, not gonna be able to make it. If I send you $50 can you figure out a way down here?
Terrified.
So we sat there, drinking.
“Church performance of what?”
Allow me to explain.
That night, I find out Aaron is coming over.
“I give up.”
It was a commercial office building next to a gym, with no bathroom inside.
“You're not CHARGING HER?”