EPISODE · Mar 13, 2026 · 44 MIN
Cringey Dating Stories
from Stop The Internet · host Kelee Bovelle
In this episode, Erin and Kelee read cringey dating stories and react to some of the most awkward, bizarre, and unbelievable first date experiences people have shared. From dates running from the police to someone dumpster diving on a first date, these stories had us shocked, laughing, and questioning how some people behave while dating. We talk about dating app disasters, ghosting, weird first impressions, and major dating red flags, while sharing our own thoughts about why people act this way on dates. Along the way we also discuss situations like someone revealing they have a fiancé during a date, a person who claimed it “wasn’t a date” after meeting on a dating app, and the strange moments when a simple dinner order somehow turns into a meltdown. If you enjoy funny dating stories, awkward first date moments, relationship red flags, and real dating experiences, this episode is for you. 00:00 Introduction + Reading Cringey Dating Stories 04:16 Cringey Dating Stories Begin 04:56 Date Disappears Into the Woods (Awkward First Date Story) 05:58 When You Can’t Understand Your Date at All 10:02 My First Date Ran From the Police 11:54 Dumpster Diving on a First Date 13:31 Would You Eat Pizza From the Trash? 16:36 He Told Me About His Fiancé During Our Date 20:45 Dating Red Flags: When People Completely Miss the Point 27:01 She Left in the Middle of the Date 28:17 “It Wasn’t a Date” After Meeting on a Dating App 28:48 Controlling Behavior on Dates: Major Red Flags 31:02 Experience With a Matchmaking Service 36:07 My Date Said His Family Members Were Going Missing 37:24 Insulted Me Immediately on Our First Date 38:13 Getting Ditched During a Date 38:29 She Left Without Saying Goodbye 39:36 Ghosted Me… Then It Got Even Weirder 42:35 My Food Order Made Him Cry on a Date
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Cringey Dating Stories
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