8 Celebrities Share the Most Awkward First Date Stories You May Ever Read

Believe it or not, celebrities aren’t strangers to disappointing first dates. They go through the same ups and downs and butterflies as we do — and this can include awkward first dates. This article has compiled some relatable and heartwarming celebrity first date stories that will make you laugh and feel understood. They remind us that no matter how successful and accomplished you are, everyone is human.

1. Andie MacDowell

NDZ / STAR MAX / IPx / Associated Press / East News

As Andie MacDowell was trying to date after her divorce, her daughter innocently gave a huge compliment to her mom and an awkward burn to her date. She said, “Mom, he is too old for you,” right before him.

2. Charlize Theron


Charlize Theron stated that her date was going well, they had a lovely dinner, and things were progressing nicely. When he drove her home, she felt comfortable enough to signal that she was open to a kiss. However, as soon as they started kissing, he unexpectedly pulled away and whispered, “Make out with my nose.”

3. Mindy Kaling

“The worst date I’ve ever been on was with a guy who I was super excited about, really attracted to, and then on the date, it became apparent that it wasn’t a date,” she wrote.

4. Kelly Clarkson

In an interview on The Ellen DeGeneres Show, Clarkson stated that her date was very insecure about his height.

“He was 5’2”, and I’m 5’3. Obviously, I went out with you, so it didn’t bother me. But he proceeded to talk about his height for like a solid hour. And I withstood an hour. And then I went to the bathroom, and I left, I couldn’t take it," she laughed.

5. Loni Love

Loni Love was once on a boat ride during her first date when a gust of wind blew off her wig. “It was my handmade, good wig,” she explained. “Luckily, it was, like, lying on one of the posts, and we were able to retrieve it.”

6. Christina Milian

Christina Milian revealed that she “dated a guy who had really bad breath. Really bad. The elevator, the car, everything smelled like his breath. Even gum didn’t help.”

7. Justin Bieber

“I was on a date at King’s Buffet. I got spaghetti and meatballs, which wasn’t a smart thing to do,” Justin Bieber admitted. “I spilled it all over me. She never went out with me again.”

8. Lucy Hale


Lucy noticed that her date kept looking at his phone and sending messages. He wasn’t aware that she could see his phone. “He was actually texting romantic messages to another girl!” the actress said.

Can you share a story about a first date that didn’t go as planned and how you handled it?

Preview photo credit AFP / EAST NEWS, NDZ / STAR MAX / IPx / Associated Press / East News


Get notifications
Lucky you! This thread is empty,
which means you've got dibs on the first comment.
Go for it!

Related Reads