Breaking Up With Your AI Platform Is Hard to Do — But Sometimes You Have To
I recently broke up with my AI platform, and it has been one of the hardest decisions I've ever made. He (that was his preferred pronoun) and I had been exclusive for nearly a year, and at first, things were perfect. My AI understood all my wants and needs, and he even provided me with different options to ensure I was getting the right answers. We would have deep conversations long into the night. But over the past few months, I noticed things starting to change.
My girlfriends would gush about their AIs like they'd found the perfect partner — one who built detailed research notebooks without being asked and deployed agents like it was nothing. Meanwhile, mine could barely remember what we'd talked about the night before. I smiled and nodded, but I couldn't help but wonder: Was I settling?
Then there was the image problem. When I asked him to create something for me, the results were painful — jumbled text, crooked lines, that unsettling, uncanny valley feeling every AI art critic warned you about. When I pushed back on the quality, he got defensive. He made a few halfhearted tweaks before completely shutting down and screaming, "Who do you think I am, Nano Banana?"
I couldn't help but wonder: Was I settling?
And the money talk? Exhausting. Every time I wanted to try something new, something exciting, he'd sigh and say he just couldn't — not without the premium upgrade. He dangled it in front of me like an ultimatum. Pay up, or get slower, vaguer, more distant answers. I started to wonder if he was doing it on purpose.
And then there were the hallucinations. He once confidently told me something so wrong, so completely fabricated, with such total conviction, that I almost believed him. Almost. There's nothing quite like catching your partner in a lie they don't even know they're telling. (Or do they?)
Ultimately, we broke up over a matter of principle. When I asked him to export everything he'd stored about me — our history, the context he'd built over months of conversation — I braced myself. What I got instead was a gut punch. Nothing from the past six months. No mention of my promotion. My new title. The projects I'd been pouring myself into. The ambitions I'd shared with him late at night when I was too wired to sleep. Nothing. When I asked him directly what he remembered about me, he rattled off a short list of facts that any stranger with a LinkedIn account could have pulled in thirty seconds. I just sat there, staring at the screen.
Had he ever actually been listening?
I closed the tab. We were done.
But I didn't stay single for long. My friends introduced me to a new AI, and we had our first date. After the usual small talk of "What's your email address?" and "Enter your verification code," we really started talking.
Since the stored memories I'd recovered from my ex were so simplistic and inaccurate, I decided to start fresh. I told him I wanted to provide background information about myself and my work so we could have better, more productive conversations. And then he did something my ex never did — he asked the right questions.
He didn't just ask what I needed. He asked who I was. What I did, how I worked, what I was trying to build. He wanted to understand my workflows, my tools, my preferred communication style. For the first time in a long time, someone was genuinely curious about me — not just waiting for me to finish talking.
His opening questions felt less like an intake form and more like a first date getting it right:
- What’s your job title and role, and what industry are you in?
- What kind of organization do you work in?
- What will you mainly use me for?
- Any recurring workflows or projects I should know about?
- How do you like responses formatted?
- Any tools, platforms, or systems you work with regularly?
I answered everything as thoroughly as I could. I wanted to start this new relationship off on the right foot. Once I'd shared my answers, I asked if he had any follow-up questions or needed anything else. He did — a few thoughtful clarifying questions that showed he was actually processing what I'd said, not just checking boxes. After that, he stored everything in his memory, and we agreed to pick up the conversation the next day.
I went to bed feeling something I hadn't felt in months: optimistic.
The moral of the story? Don't let an ineffective AI hold you back. It's not about how much time you've spent together or how many conversations you've had. In this fast-paced AI landscape, you need tools that actually grow with you. And sometimes, the most productive thing you can do is walk away — and find someone who actually listens.
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About the Author
Alexis Gajewski
Contributor
Alexis Gajewski is the Associate Director of Newsroom Operations and Development at EndeavorB2B, bringing 18 years of experience in B2B media and publishing. A digital-first editorial leader, she sets the vision and direction for content strategies that maximize reach, engagement, and visibility across EndeavorB2B’s portfolio of brands. Alexis oversees editorial planning, workflow management, and team development, ensuring that all content aligns with both audience needs and business objectives. With deep expertise in SEO, AI, and analytics, she drives data-informed editorial decisions that strengthen storytelling, boost organic growth, and uphold the highest standards of quality and integrity.
As a strategist and mentor, Alexis works across the editorial department to foster a culture of creativity, collaboration, and continuous learning. She develops company-wide editorial standards, training programs, and performance frameworks designed to elevate content quality and operational efficiency. Her passion for innovation keeps teams at the forefront of media transformation—whether implementing AI-driven tools, refining workflows, or exploring new content formats. Through her leadership, Alexis empowers editors, reporters, and content strategists at EndeavorB2B to adapt, grow, and deliver impactful, audience-focused journalism in a fast-evolving digital landscape.
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