What is your biggest mistake or regret?
10.06.2025 03:41
“It's milk, Mary.”
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.
The car meant freedom.
Is it considered rude to comment on someone's weight? Is it simply stating a fact?
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.
“You're not CHARGING HER?”
My life since then has been relatively calm. Mary's, to my knowledge, has not been.
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.
“To the dog park!”
“Sully here wants to become a tattoo artist, you love tattoos don't you Aaron?”
“Hey Sully, guess where I'm living right now!”
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.
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.
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?”
She was deadly fucking serious.
That night, I find out Aaron is coming over.
Is a man over 50 not married no kids a red flag?
“Absolutely not!”
I was exhausted. I wanted to go home and sleep but no, this bitch wanted to go fucking party.
I don't say anything.
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I felt broken.
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.
“Nope!”
What does success really mean to you? Is it about happiness, money, or something else?
It was my hope box.
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.
He comes over, and at this point I have no idea what she's told him.
As for me, I'm doing pretty good for myself.
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.
“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!”
Why are Republicans such intolerant people?
I cried in the corner.
“$50? I thought we agreed on a lot more?”
“Please, you made some fliers! I could make fliers!”
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My stupid fucking ass says “How much?”
I should have taken this as a sign from God himself to say no and stay put.
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.
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.
She says “Honey, you're not getting my car for $2600.”
I have no idea how Mary managed to convince him to come over- oh no wait, yes I do.
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.
I had her drop me off at a McDonald's.
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.
“Uh, in Stuart?”
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.
“Where?”
Despite every red flag in the world getting flashed in my face right then, my dumb ass said yes.
“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!”
“I give up.”
However the hell she thought that would work!
She threw things around and tried to break shit and yelled at me to stop.
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.
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?
“But I thought you said-”
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 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.
$50 has hit your account!
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 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.
“But you got it for free from the church, you said that-”
“I'm in the keys! I'm living in the keys!”
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.
I didn't.
“No, I know him. He's probably fucking some girl tonight. Come on, I need a drink.”
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.
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.
“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?”
She paid me back, of course, but I still found it weird that she couldn't figure out how to do that part herself.
Now, why on earth would two people without a dog be heading to a dog park at 6PM?
This was not spunk.
I fell in love with it, and I felt so, so hopeful.
“Oh come on, one little drink won't hurt you!”
“No, I don't drink anymore, I wanna go home.”
Then she has the fucking GALL TO SAY THIS, “Do you think I should be charging the yoga teacher for using the studio?”
Well to stalk her ex-boyfriend Aaron of course!
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.
“There's plenty more where that came from once the studio is up and running!”
“By the way, in the mornings I'm renting this place to a yoga instructor so we have to be out by 5AM.”
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.
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.
Furious.
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.
The moment the money changed hands, things got even worse.
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.
“No!”
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!
I told her no.
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.
It was a commercial office building next to a gym, with no bathroom inside.
So we go to another bar.
“No, this is from a man, this is spunk.”
“You got the money for one?”
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.
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.
“Yeah but she's a friend of mine, I don't wanna piss her off.”
She comes to me and says, “Sully, I need you to come look at something.”
Good for him though, just as we were pulling in he was leaving.
Eventually, after several hours, we both calmed down.
“Or its nighttime and he just wants to go home?”
My heart was racing, could this be it? My big break? My chance at making an income and a name for myself?
At a completely made up, completely impossible scenario.
This is a long one so buckle in.
Except this bitch has the gall to say, “You know, I really need a new car.”
That night I asked her when she'd be giving me the keys to the car.
“Maybe you could get Sully a job tattooing around here, you know lots of people don't you?”
“You don't get it! You don't get it because you've never been in love! I need him, Sully, please help me!”
And now Mary was down there, living it up according to her.
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.
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 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.
“Nope!”
And she was on his Facebook. Again.
Now, there was one thing I didn't bring with me before I left. My savings.
She had previously been a performing arts instructor, and was currently a divorcee with two kids she was fighting for custody of.
“Babysitting? You told me I was gonna be your graphic designer for the performing arts studio.”
All because I wanted freedom.
That wasn't happening, but he still let me stay regardless. It was my goal to get a job and get out ASAP.
Something that would actually make it reasonable to be snooping around your boss’s goddamn bedroom, I was sure.
That moment in McDonald's was in itself an adventure, but I did, eventually, make it back home safe and sound.
“You see that?”
I'll always remember that man as an angel, because he really was an angel for me.
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.
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?
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.
I walked out.
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.
And I paid Mary for her car.
“Oh come on, I just need him around long enough to convince him to stay with me, please?”
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 moved here because I was a fucking idiot.
Mary moved here to stalk Aaron.
We never got a hit, and she never put anymore effort into the endeavor. It was dead within the week.
He picked me up and got me back safe and sound.
Now, I want you to put yourself in my shoes for a moment.
“5AM? Where the hell are we gonna go at 5AM?”
$2600.
For a shitty van.
In the Keys of all places?
“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!”
He leaves, and Mary is erratic as hell over it.
I had met Mary about a year prior to this incident back when we were both homeless.
“Can you just act kinda flirty towards him? I want him to think he's gonna get with you.”
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.
She's standing in the doorway of her boss's bedroom.
Another bar fucking Aaron just so happened to be at.
Next day, similar dig.
Immediately, she packs up the kids in the car and takes us all to a phone store.
For the next eight hours I worked out a way to get back home.
“I do. Listen, I gotta go-”
“I really gotta go, Mary. Nice meeting you, Sully.”
“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 had him transfer the money to my account.
I leave the room and return to the kids.
“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!”
The following morning she asked me if I would stay.
The following morning she woke me up at 5AM, and rushed me out the door.
She proceeded to self destruct.
With my hard earned cash.
“PSL?”
“Wait, let's get a drink, Sully don't you wanna go get a drink with Aaron?”
I accepted that I literally had no choice but to stay there at least one more night.
“Yeah, they're cool.”
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.
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.
“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!”
Nearly a year later, in September of 2019, I get a call from Mary.
“The milk stain?”
Terrified.
“They probably do! They both know me so they probably know each other!”
“I bet he's meeting a girl. Probably has a date with her.”
“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.”
“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?”
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.
“I guess that depends.”
Where she buys herself a nice new fancy phone.
It was not an apartment.
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.
I gotta get away from her, and she's apparently offering me a car now.
I look at her face, and I felt like a deer locking eyes with a mountain lion.
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.
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.
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.
I know what “spunk” looks like.
It somehow gets even worse.
Turns out, Aaron lived in the Keys now. Aaron moved here to get away from Mary.
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.
Allow me to explain.
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.
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.
I follow her into the room and she points at, what is very clearly, a milk stain.
So we sat there, drinking.
“How much you got?”
“I do, I been saving up. But I'd be willing to sell my current one to you if you want.”
Then slap yourself in the face for the following thought process.
“Do they even know each other?”
“But if she hasn't paid you then she has the entire building for free!”
$2600, gone.
She had an ex-boyfriend, Aaron, who she never stopped talking about.
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,
“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.”
“Church performance of what?”
“No. It's from Aaron. She's been fucking Aaron.”
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.
Next day, the climax.
She was trying to frame me.
“To work, silly! We're gonna be babysitting like I told you.”