7 worst date choices made by Rachel in Friends

Rachel Green’s dating life on Friends was full of wild choices and awkward situations.

She started by running out on her wedding, and it only got messier from there. Over ten seasons, she went on dates that were confusing, badly timed, or just flat-out terrible. Some of them were meant to help her move on. Others were about making Ross jealous. A few looked fine at first, but quickly turned into disasters.

She didn’t lack confidence or charm, but her choices often felt like she was trying too hard or not thinking at all. She got back with her ex-fiancé. She went out with men who were not ready or right for her. She made impulsive decisions that often led to awkward or painful endings. Watching her go through these moments was equal parts funny and frustrating.

This list is not about casual missteps. These were the seven worst dates Rachel ever had on the show. These are the ones that made fans shake their heads or look away from the screen. Each one stood out for just how badly it went and how clear it was that Rachel should have said no. Let’s break them down.

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7 worst date choices made by Rachel in Friends

1. Barry (Her Ex-Fiancé)

Rachel went back to Barry even though she had left him at the altar. That moment defined the beginning of her journey on Friends, and going back to him felt like erasing all that growth. Barry was now engaged to Mindy, who used to be Rachel’s best friend.

She still chose to hook up with him. One scene even showed them fooling around in his dental clinic while he was cheating on his current fiancée. It was messy and selfish, and it didn’t reflect well on Rachel’s character. Monica tried to talk sense into her, but Rachel wasn’t ready to listen.

The disaster peaked when Mindy showed up and Barry’s two-timing came to light. Rachel realized Barry hadn’t changed, and neither had the reasons she left him. It was a complete backslide and served as a reminder that comfort doesn’t always mean safety or love.

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2. Joey Tribbiani (Her Close Friend)

Rachel and Joey tried to turn a solid friendship into something romantic. It never worked, and it showed from the first kiss in Barbados. Neither of them looked comfortable. Both were picturing Ross at the moment. It wasn’t chemistry. It was confusion.

When they tried to go on an actual date back in New York, things got worse. Rachel slapped Joey every time he made a move. Then she accidentally hit him below the belt. It was supposed to be playful, but it ended up being awkward. There was no rhythm or spark between them.

This attempt at romance confused fans and undercut their well-written friendship. It felt like the writers had run out of ideas and were forcing something just to shake things up. In the end, both of them realized this was a mistake. They agreed to stay friends. That was the right call and one they should never have questioned.

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3. Tommy (The Screamer)

Tommy seemed normal when Rachel first met him. He dressed well and acted politely in public. But Ross caught him losing his temper with an old man and tried to warn everyone. No one believed him because Ross was the insecure ex-boyfriend.

Rachel kept seeing Tommy until the moment he screamed at the chick and duck. He called the duck “Donald Dodo” and yelled like a maniac. This happened in the hallway where everyone could hear him. It confirmed Ross was right all along.

This date was a failure, not just because of Tommy’s behavior. It showed how Rachel ignored serious red flags. She picked someone who could easily snap just because he looked put together. The moment gave Ross one of his rare vindications and reminded the audience that charm can cover up a lot. This meltdown turned Tommy into one of the most memorable minor characters on the show.

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4. Danny “The Yeti”

Rachel first saw Danny in the building's basement and thought he was a criminal. She maced him without asking questions. The moment was wild and intense and unforgettable. But somehow she still ended up dating him once he shaved and cleaned up.

He seemed normal until Rachel met his sister. Their dynamic was unsettling. He licked dessert off her fingers. She wiped his pants while crouched in front of him. He said they were going upstairs to change clothes together. This all happened at Central Perk in front of Rachel and the gang.

Rachel bailed out quickly after that. She didn’t wait for more signs. This was one of those dates that looked fine at the start but kept getting worse the more you learned. Danny’s story ended almost as suddenly as it began. It became memorable because it was so strange and disturbing in a very real way.

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5. Joshua (Her Client)

Rachel met Joshua at Bloomingdale’s and quickly became obsessed with impressing him. She bought expensive sheets and got Monica to cook. She wore new lingerie and planned everything down to the last detail. It wasn’t a date. It was an operation.

Joshua got uncomfortable the moment he saw the chick and the duck in her apartment. Rachel tried to push through and even followed him to his parents’ house. That backfired. She was in a nightgown when they walked in. They thought she was a hooker.

This wasn’t just a bad date. It was a train wreck of high expectations crashing into total disaster. Rachel looked desperate and out of touch. The date with Joshua was supposed to be her big moment. Instead, it became one of her most embarrassing episodes. Nothing about it worked, and Joshua vanished after.

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6. Michael (The Cat Talk Date)

Monica set Rachel up with Michael just as she was spiraling over Ross and Julie. Rachel had just heard they were getting a cat together. That news broke her. She went into the date rattled and not ready to meet someone new.

She sat across from Michael and asked bizarre questions about pets and breakups. She wanted to know how long cats live. She asked if he ever bought a pet with an ex. She even got drunk and used a stranger’s phone to leave Ross a message.

Michael never stood a chance. He didn’t do anything wrong. He was just stuck in a bad moment with someone who had no business dating that day. This scene stood out because it wasn’t funny. It was raw and sad and honest about how breakups can wreck your judgment. Rachel’s spiral dragged Michael into it and left a lasting impression on viewers.

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7. Kash (The Actor Who Bolted)

Kash was Joey’s co-star and seemed like a decent guy. Rachel met him while already dealing with her pregnancy. She didn’t hide it and told him the truth during their date. That’s where things fell apart. Kash panicked instead of stepping up.

He didn’t handle the news well. He blurted out something about hemorrhoids and got visibly uncomfortable. That was it. No support. No conversation. He ditched her and left her alone on the street. All she had were some candy bars she picked up earlier.

This wasn’t a long relationship or a messy entanglement. It was a simple date that turned into a cold rejection. Kash wasn’t awful. He was just unprepared and inconsiderate. This moment reminded fans that honesty doesn’t always bring kindness. It showed Rachel trying to be brave and getting nothing in return.

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