Gosselin went out with a man named Andrew and there were several silent pauses with very little conversation. She later called the date "painful."
The one thing he did say that rubbed Kate and her daughter the wrong way was calling her a "celebrity."
In behind-the-scenes images the mother of eight shared on Instagram, she wrote, "Oh, Mady! The things she picks up on!"
She added, "This guy said the WORST thing you can ever say to us.... like nails on a chalkboard to us! And Mady had to take note of it while watching the clips!"
Things aren't going all that well with the other men either. Apparently a man named Nick stood her up.
"As I waited for #NoShowNick I couldn’t help but stare at the ceiling ... I was surrounded by cats!" she shared in another Instagram image.
But at least her camera man Danny kept her company.
She added later, "Watch next weeks #KatePlusDate — I’m NOT KIDDING, you’ll laugh the entire time! It was SO MUCH FUN!" So something must have gone right.
Bad dates aside, Gosselin is really opening up for the show and growing.
The woman who divorced her ex-husband Jon Gosselin almost a decade ago opened up to her matchmaker about her divorce, saying that "it hasn’t been pleasant," in a preview clip obtained by People magazine.
Mady added this week that the divorce from her dad really gave her "trust issues."
It's been a busy year for Kate and her kids.
Earlier this year, twins Cara and Mady graduated from high school and their mom couldn't be more proud.
"I’m still beaming with pride! It’s hard to believe that Cara and Mady graduated from high school this past weekend," she wrote. "And are headed off to college in the fall! Where did the time go????"
"Kate Plus Date" airs at 10 p.m. EST Mondays on TLC.