I used to fuck a chick named Mimi. That’s not her real name. I knew her cause in sixth grade I made out with her older sister at a house party I was having at my parent’s house, and then twenty years later I was smoking a joint in someone’s car outside of the Nassau Community College theatre department and I told  the hot chick in the front seat my last name and she was like YOU USED TO MAKE OUT WITH MY SISTER! Anyway, that’s how we reconnected. And when I found out she was living in LA years later, it only seemed right I should hit her up on Facebook (Instagram wasn’t invented yet) to let her know I was also in town. That’s the first sign of poor boundaries in relationships: trying to bang the younger sister of the girl you got to sloppy second base with in middle school. Anyway, that’s not even the point. Point is, we got together and fucked for about a year or so and then we stopped fucking when I got sober and eventually I hired her as my personal assistant, and that’s what I wanna tell you about…

Really Bad Boundaries in Relationships

But first lemme tell you this: Mimi became a lesbian for a short while after our sex affair in LA. That little fuck tirade went on for about a year before she moved back to New York and fell in love with the hottest little half Asian chick. I tried to negotiate a threesome in Brooklyn with the both of them but it ended terribly. It all started when she was looking for an apartment in New York and I still had my old apartment in Brooklyn that I was paying rent for even though I also had an apartment in Los Angeles. So, I just told her I would keep my apartment in Brooklyn and she could rent it from me.

But the thing is, she couldn’t afford it. So I offered her a lower price than the rent I was paying. She accepted that deal, but now I was basically paying to keep her and her girlfriend in my apartment so that whenever I went back to New York to see my family I could have sex with them. But the sex never happened. On the night we were all supposed to fuck, we did a bunch of cocaine and I made out with her girlfriend at a bar when Mimi was in the bathroom and then when Mimi came out of the bathroom her girlfriend told her that we made out. She did it to make Mimi jealous. They had a weird codependent relationship, which made setting boundaries in relationships absolutely impossible. Anway, she and Mimi got into a fight and the threesome never happened.

That wasn’t the last of my attempts though. I tried to fuck em both a few more times before finally I gave up. It was supposed to be the greatest accomplishment of my life. I had not much to feel good about in my life and needed this for my self-esteem. It was around that time that I got sober. Nothing in my life made sense and all the relationships in my life were burnt to a crisp. So I went back to LA to try and get my life together.

How to Set Boundaries in a Relationship with Ex-Fuck Friends

crossing the line

So yeah, I’m now sober at this point, and after a year or so of catering tables with about one year of sobriety, I got an internship at a PR firm. A new life, I thought to myself. I worked there for a few months and then quit cause I was twenty-eight and they only offered me 30K. 30K? Fuck you. I quit.

Well how much do you want?

10K a month.

Okay we can’t do that.


It didn’t take long before I signed my own client and I had myself a blossoming PR agency. 

Fast forward about a year.

I was barely making enough money to hire a personal assistant, but that didn’t stop me from texting Mimi. I had about 11 clients and was pulling in like 40 grand in revenue per month so I thought I was rich. Won’t she be impressed with me now… I bet she’ll wish that threesome happened ten times over…

But that aside, what I didn’t realize was I hired so many people and never calculated the payroll taxes that I was actually losing money when all was said and done. But anyway, I needed a personal assistant, so I texted Mimi who I hadn’t talked to in a while and asked her to do it. She came over right away while my then (new) girlfriend was over and began re-doing my fridge. If I ever had any intention of setting boundaries in relationships I probably woulda started there–before she itemized my fridge, but I knew she was still wanting to fuck me and it turned me on that she was in my kitchen. I know I sound horrible but that’s just what it was, okay?

The Most Fun Comes When I Have Shitty Boundaries in Relationships, But Nothing Good Was to Come From This…

Soon she started sayin shit like, “you know you still want me” and “wouldn’t I make a great wife?” All that stuff. I really liked it. I liked having shitty boundaries cause it made me feel like I was wanted. It made me feel like if the relationship I had with my then-girlfriend failed, which it did, I could still get my self-confidence from Mimi. Of course that’s not the way it worked out. But still she organized my room and tried to handle business tasks, but she wasn’t very good at it.

That was the whole reason I hired her. She couldn’t do the business shit but could cook my lunch and rearrange meetings, so maybe that shoulda been a sign that she wasn’t fit for the job. But her tits were huge and I knew her sister and her mom used to let me crash at her house in Long Island whenever I would run away from my parents. So, what I’m saying is there was history. 

That’s one big reason I was never able to get good at setting boundaries in relationships: because I was always thinkin about the history of that relationship. There was always so much there. But of course there was. I mean, I was a crazy fuck and the only women I let into my life needed to be fixed. But the reality was I was the broken one who needed to be glued back together so although I kept lookin for chicks I could help, I was the pitiful one. Anyway, I digress…

We went out to a piano bar in Los Angeles and bumped into Ryan Gosling. We had a funny encounter and then that added to our history. She went on dates with other guys and I got a tiny bit jealous and she liked it. We were basically in love with fuckin with each other. I just couldn’t put her down. Besides, she was always complimenting me. How could I leave her? Leave her? Oh man. I’m not leaving her. She’s my employee. I mean, more than an employee obviously. I love her. Wait… See? That’s how my head was working. Fucked up. 

How to set boundaries in relationships is to probably not be so invested in the outcome of the other person. 

All I wanted was for her to be happy. If she couldn’t find a dude to make her happy, I would do the job. So what if I had a girlfriend?

But then she left me. Eventually she got a better paying job–I think I was paying her minimum wage–and we parted ways. So now I was free to be in a healthy relationship… but all that happened was I began reaching out to her ex-girlfriend, the one I really wanted to have a threesome with. Then that became a thing. The moral of this story is there is no way have a healthy relationship with someone else if you don’t have a healthy relationship with yourself. To be setting boundaries in relationships with other people when you don’t even know how to treat yourself is an uphill battle that you’ll lose. Focus on that shit first.

Now here’s that story about Ryan Gosling.

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