After more than 30 years in real estate, I can say with certainty that not everything goes according to plan. In fact, some of my most memorable moments have come from the bloopers, blunders, and laugh-out-loud situations I’ve experienced along the way.
I’ve often joked that those of us who have been in real estate for decades should write a book. While I don’t have the time to tackle that project, I thought it might be fun to share a few of my favorite stories here on the blog—one at a time. These lighthearted memories remind me to stay humble and keep a sense of humor.
Early in my career, I received a referral that felt like a golden opportunity: the parents of a famous sports figure were looking for a beachfront condo. I was thrilled—though if I’m being honest, I wasn’t exactly seasoned at showing condos.
Anyone who has worked in real estate knows how tricky condos can be. Elevators that leave you disoriented, owners who forget to mention tenants are still in residence, and a dozen other awkward surprises are always possible. Still, I was determined to give this couple my very best.
I spent hours preparing before picking them up at our agreed meeting spot. Once they were in the car, I tried to strike up a friendly conversation. Dead silence. If you know me, you know I can’t stand silence—I feel compelled to fill it. So, chatter I did… all the way through ten different condo showings. By the last one, my voice was nearly gone, and I was sweating bullets.
Finally, we pulled up to the last condo of the day. I jumped out of the car, relieved that this marathon tour was almost finished. We walked through the unit, they said nothing, and we headed back to the parking lot.
That’s when I noticed something alarming: the car was gone.
In a panic, I blurted out, “Oh my gosh—my car is gone!”
The gentleman, completely calm, looked at me and replied, “No, it’s over there. You forgot to put it in park, and it rolled down the hill and turned itself around.”
Miraculously, it hadn’t hit another car. I was mortified. Needless to say, I never heard from them again.
Looking back, I can laugh at the story. At the time, though, I wanted to crawl under a rock. Experiences like this remind me that real estate isn’t just about contracts and closings—it’s about people, unpredictable moments, and rolling with the unexpected (sometimes quite literally!).
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✨ Do you have a funny or cringe-worthy story from buying, selling, or even just touring a home? I’d love to hear it—share your story! And if you enjoyed this post, stay tuned for more of my favorite real estate bloopers and behind-the-scenes moments.