Jennifer Aniston’s Blind Date That Went Hilariously Wrong

Dating in Hollywood is often a risky business. Actors are in the spotlight, and the media and fans capture every move they make. Rarely can they enjoy a quiet night out or keep a relationship secret.

Fans love hearing about celebrity relationships, whether it’s a blind date, a celebrity marriage, or a scandalous affair

Jennifer Aniston is a fan-favorite

Jennifer Aniston on the red carpet
Jennifer Aniston | Axelle/Bauer-Griffin/FilmMagic

Jennifer Aniston is a celebrated actress who made a name for herself in the ’90s with the show Friends. She became an overnight sensation and went from anonymity to internationally recognized. Her dating life became public as well. She went through a very public breakup with husband Brad Pitt and later new husband, Justin Theroux.

After friends, she went on to star in movies, such as Bruce Almighty (2003), The Break-Up (2006), Marley & Me (2008), He’s Just Not That Into You (2009), and We’re the Millers (2013).

Most recently, she starred in Netflix’s Murder Mystery with Adam Sandler and Apple TV’s The Morning Show. When she finally joined social media recently, she set a Guinness World Record: it took only 5 hours and 16 minutes to reach 1 million followers on Instagram, beating the record previously held by Prince Harry and Meghan Markle’s account.

With a net worth of $220 million, she’s doing quite well for herself. Aside from the money she still makes from Friends reruns, she also does a lot of endorsements. Since she’s still in the spotlight, so is her dating life. 

Jennifer Aniston’s hilarious blind date

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Girl’s best friend… bring Clyde to work day.

A post shared by Jennifer Aniston (@jenniferaniston) on

Before she married Pitt, Aniston went on a blind date with former talk show host Jon Stewart. When she visited his show in 2010, they reminisced about a time when they had been on a date.

The date occurred over 20 years ago now, and of course, their memories of the night were a bit different. His view of things was that it was supposed to be a romantic Italian dinner in NYC.

He asked her out, but she showed up with friends. He joked that he actually thought that it meant she was so excited to go out with him that she wanted him to meet her friends. She, on the other hand, remembered it being an invite where he said a group of friends was going out and he just invited her to come along, so she invited her friends.

The humorous miscommunication ended up with them remaining friends, and the two never actually dated. 

Who is Jon Stewart?

Jon Stewart is best known for his time on The Daily Show, which he hosted the show from 1995 to 2015. He’s a comedian, writer, producer, and director. Since leaving The Daily Show, he’s also appeared on talk shows and has directed a film. He’s also been a staunch advocate for 9/11 first responders.

Along with activism, which has been a primary focus for him, he’s also about to go back behind the camera.

The comedy film centers on politics and is called Irresistible. Ironically, it’s produced by Aniston’s ex, Brad Pitt, and his company Plan B Entertainment. It also stars Steve Carell, Aniston’s co-star in The Morning Show. Stewart has been married to Tracey McShane since 2000. 

Other celebrity blind dates

Celebs go on some weird dates, and there are plenty of stories capturing them. Blind dates are pretty common, too, and lead to quite a few celeb marriages. Carrie Underwood and her husband Mike Fisher met on a blind date.

Even Stewart met McShane on a blind date. Justin Timberlake also met his wife, Jessica Biel, on a blind date. It sounds like blind dates are a successful way to meet spouses, after all.