Jennifer Aniston's Most Awkward Dating Stories

Despite Jennifer Aniston's impressive Hollywood career, ranging from her iconic role in "Friends" to several hit romantic comedies throughout the early to mid-2000s, the public can't get enough of the actor's love life. Aniston was famously married to Brad Pitt from 2000 to 2005 and later to Justin Theroux for just under three years until their 2018 divorce and has also been linked to several other high-profile celebrities like John Mayer and her former co-star Vince Vaughn.

Since the TV icon's second divorce, Aniston has reportedly been resolutely single but she remains open to finding love. However, her taste might be the problem, at least according to Aniston's long-time friend and fellow actor Adam Sandler. During a 2023 appearance on "The Tonight Show Starring Jimmy Fallon," Aniston admitted that he often criticizes her dating choices. "If I get anything from him, it's 'What are you doing?' — usually based on someone I'm dating," she shared.

Well, according to an Us Weekly source close to the star, Aniston is really just looking for the basics in a relationship: "chemistry," "humor," "good looks," and "kindness." Another insider, speaking to Life & Style magazine, revealed that she would even be open to dating someone outside the celebrity realm. Despite not being high maintenance, Aniston has sadly endured some less-than-ideal dates, proving that even Hollywood stars face challenges in the quest for love.

Jennifer Aniston and Jon Stewart once had such an awkward date that the talk show host couldn't help but bring it up as soon as she joined him on "The Daily Show" in 2010 — despite the fact that it had happened over a decade earlier. In front of the cameras, Stewart humorously recounted inviting Aniston to a romantic rendezvous during the first season of "Friends." However, upon arriving at the Italian restaurant, the talk show host quickly realized a miscommunication had occurred as Aniston was accompanied by a group of friends. 

He quipped, "And I remember thinking, 'She's so excited to be on a date with me, she wants me to get to know her posse.'" Regrettably, for him, the TV star's intention was a group hangout, not a one-on-one date. Aniston jokingly responded, "It shows my commitment to 'Friends.'" While it's unclear how exactly things got going between Aniston and Stewart, their flirtatious dynamic was captured in a 1995 interview. 

During Aniston's appearance on "The Jon Stewart Show," the doomed couple displayed evident fascination with each other. Upon sitting down, Stewart playfully put his arm around Aniston as he stretched, after which she complimented the comedian's eyes and even told him he was cute. There's a strong possibility he asked her out afterward, and one can only hope it went more smoothly than their awkward date.

Despite being one of the most well-known faces in Hollywood, Jennifer Aniston was surprisingly open to going on blind dates. However, her attitude might have shifted after an exceptionally rough one. According to an insider who spoke to Life & Style and is reportedly close to the "Murder Mystery" star, one of Aniston's worst blind dates involved a Hollywood studio executive who, in a rather awkward manner, turned their supposedly romantic evening into a business meeting. The source detailed, "After a few minutes of small talk, he pulled out a screenplay for a slasher-horror-film-meets-rom-com he was working on." 

As if that wasn't bad enough, the unnamed executive continued sharing his vision with a visibly baffled Aniston. "Not only did he write it, but he also wanted to be in it, opposite Jen as the star. She was flabbergasted," the insider asserted. Evidently, she declined the job proposition from her overly confident date. It's clear why Aniston deems romance difficult. As she acknowledged in an interview with The Wall Street Journal, "It's just about not being afraid to say what you need and what you want. And it's still a challenge for me in a relationship." One thing is certain — she does not want a business proposal during a blind date.