Let’s talk about bad dates — because if you’ve been single long enough, you probably have at least one story that makes you laugh and cringe at the same time. My friend and I were reminiscing recently about some of our dating disasters, and that’s when I remembered this absolute gem of a first date that still makes me shake my head.
So, a while back, I matched with someone on Tinder. He seemed nice enough — funny, decent photos, and he could actually hold a conversation (a rarity in the app-dating world). We decided to meet at a park, and honestly, things started off really well. We were chatting on a bench, enjoying the day, and for a brief moment, I thought, “Hey, maybe this could actually go somewhere!”
And then…it didn’t.
Somewhere between small talk and life goals, he suddenly launched into a very detailed story about his ex-fiancée. According to him, she was “bipolar, crazy, and ruined his life.” I tried to nod politely, but the story kept spiraling — we’re talking cheating, pregnancy drama, open adoption, and a custody situation that sounded like a soap opera gone rogue.
Now, I’m not saying his ex wasn’t dealing with challenges, but sharing that entire emotional saga on a first date? That’s a solid red flag, my friends.
But wait — it gets worse.
As I started subtly inching away (you know, creating a healthy amount of personal space), he looked at me, smirked, and said,
“Why are you scooting away? I don’t bite… unless you want me to.”
I wish I were joking.
At that point, I wasn’t sure whether to laugh, cry, or sprint. I wrapped up the conversation as quickly as possible, made my polite excuses, and power-walked back to my car like my life depended on it.
So yeah — that was my “worst first date” story. Funny in hindsight, but definitely one for the cringe history books.
If you’ve had your own dating disaster, I’d love to hear it! Drop your stories in the comments or check out my vlog for more awkward moments, laughs, and lessons learned from the dating battlefield.
Cupcakes & Tea with Elizabeth 