Worst Dates Ever. Sir, Check Please. episode artwork

EPISODE · May 7, 2026 · 41 MIN

Worst Dates Ever. Sir, Check Please.

from Sober Opinion · host Sober Opinion

She already knew. She just stayed long enough to get the story.Six dates. A medical student with no boundaries. A man who showed up drunk to a basketball game in front of a church member who knew her mother. A blind date who argued against leaving a tip because he only made nine dollars an hour. A ten year friendship that ended the night he came back from the bathroom with an uninvited guest named KY Jelly.She knew at the parking lot. She knew at the buffet. She knew the moment the elderly woman walked over and handed her a book recommendation without saying a single word to him.She stayed anyway. We all have.Two Black women. Six disasters. Zero regrets. Because the dates that went wrong taught us something the good ones never could.Sober Opinion. Two Phones. One Truth. New episodes every Thursday.-------------------------------------------#SoberOpinion #SirCheckPlease #BlackWomenPodcast #DatingStories #BlackPodcast #TwoPhones #BlackWomen #DatingWhileBlack #WorstDateEver #BlackLove #DateGoneWrong #BlackWomenTalk #RelationshipPodcast #SheKnew #NewPodcast

She already knew. She just stayed long enough to get the story.Six dates. A medical student with no boundaries. A man who showed up drunk to a basketball game in front of a church member who knew her mother. A blind date who argued against leaving a tip because he only made nine dollars an hour. A ten year friendship that ended the night he came back from the bathroom with an uninvited guest named KY Jelly.She knew at the parking lot. She knew at the buffet. She knew the moment the elderly woman walked over and handed her a book recommendation without saying a single word to him.She stayed anyway. We all have.Two Black women. Six disasters. Zero regrets. Because the dates that went wrong taught us something the good ones never could.Sober Opinion. Two Phones. One Truth. New episodes every Thursday.-------------------------------------------#SoberOpinion #SirCheckPlease #BlackWomenPodcast #DatingStories #BlackPodcast #TwoPhones #BlackWomen #DatingWhileBlack #WorstDateEver #BlackLove #DateGoneWrong #BlackWomenTalk #RelationshipPodcast #SheKnew #NewPodcast

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Worst Dates Ever. Sir, Check Please.

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This episode was published on May 7, 2026.

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She already knew. She just stayed long enough to get the story.Six dates. A medical student with no boundaries. A man who showed up drunk to a basketball game in front of a church member who knew her mother. A blind date who argued against leaving a...

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