My AI Calendar Scheduled a Meeting with My Ex on Valentine's Day

YEET MAGAZINE
By David T. from Austin | Published: 2026-06-01T15:08:54.584Z EST
5 MIN READ

My AI Calendar Scheduled a Meeting with My Ex on Valentine's Day

I'm a marketing consultant in Miami. I rely heavily on my Google Calendar to manage my appointments, meetings, and deadlines. I've been using it for years, and it's always been reliable. I also have a personal calendar that I use for social events an...

I'm a marketing consultant in Miami. I rely heavily on my Google Calendar to manage my appointments, meetings, and deadlines. I've been using it for years, and it's always been reliable. I also have a personal calendar that I use for social events and family activities. I thought I had everything under control. I was meticulous about keeping my calendars up to date and ensuring that nothing overlapped. I prided myself on being organized. Last February, I opened my calendar to check my schedule for Valentine's Day. I had a meeting scheduled for 7:00 PM. I was confused. I didn't remember scheduling a meeting on Valentine's Day. I clicked on the meeting to see the details. It was a 'catch-up' meeting with my ex-boyfriend. I hadn't spoken to him in two years. I didn't even remember adding him to my contacts. My AI calendar assistant had pulled up his contact info and scheduled a meeting. I was horrified. I felt like I had been violated. How did the AI know about my ex? Why would it schedule a meeting with him? I was horrified. I immediately canceled the meeting. I cleared my entire contact list. I disabled the 'smart suggestions' feature. I thought I had solved the problem. It still occasionally suggests meetings with people I haven't talked to in years. It suggested a meeting with my old college roommate who I haven't seen in a decade. It suggested a meeting with a former coworker who moved to Australia. I even got a suggestion to schedule a meeting with a guy I went on one date with five years ago. It's like the AI is trying to resurrect every relationship I've ever had. I've stopped using the AI calendar features. I manually enter everything now. The AI is too invasive and keeps trying to resurrect old connections. I use Apple Calendar now but even that has AI suggestions I don't want. I've read about stopped using a bank and AI took over my money and how AI is becoming more integrated into our lives. I didn't realize it would be integrated into my personal life. Has your AI calendar ever tried to reunite you with your ex? I'm starting to think the AI has a sense of humor. Or maybe it's just trying to create drama. Either way, I'm turning off all AI features from now on.

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About the Author
David is a graphic designer in Austin who shares his experiences with automation.