The characters on Friends date a lot of people during the sitcom’s 10-season run. They’re in their 20s, so it’s perfectly natural. Many viewers relate to the characters for this reason: the characters are single, establishing their careers, and they’re dating people before settling down.
For Rachel Green (Jennifer Aniston), she has numerous dates and relationships throughout the show. She’s attractive, successful, funny, and charming. In between her on-again, off-again relationship with Ross (David Schwimmer), she has her fair share of dating experiences. Some of her dates are successful, while others are cringeworthy. Let’s take a look at her best and worst dates.
10 Worst: Michael
Poor Michael. He seemed like a great, respectful man, but Rachel just wasn’t interested in dating him. In the season two episode “The One Where Ross Finds Out,” Monica (Courteney Cox) sets Rachel up on a date with Michael, a recently divorced man. He’s nervous about the date, but Rachel is preoccupied with her feelings for Ross, who is still dating Julie.
During the date, Rachel keeps asking about cats because Ross and Julie were planning to adopt a cat together. She drinks too much and calls Ross to tell him she’s “over him.” She has closure, but even Michael can see that she’s far from over Ross. You have to give Michael brownie points for sitting with Rachel during this awkward date.
9 Best: Mark Robinson
Another harmless character, Mark Robinson (Steven Eckholdt) was Rachel’s colleague at her first job at Bloomingdale’s. At the time, she was still dating Ross and he never trusted her with Mark. He knew Mark wanted to interfere with their relationship. This argument leads to Ross and Rachel breaking up (for the first time).
After the breakup, Mark is courageous enough to ask Rachel out on a date in the season three episode, “The One With the Tiny T-Shirt.” It’s a great date between two friends, but after Mark kisses her, Rachel realizes she’s dating him for the wrong reasons.
8 Worst: Kash, The Soap Opera Star
During the show’s eighth season, Rachel is pregnant with Ross’s baby. However, they’re not a couple. So, when the opportunity arises for her to date one of Joey’s handsome costars on the soap opera Days of Our Lives, she takes it. In “The One with Rachel’s Date,” she dates Kash Ford, and everything seems great at first. He takes her on a ferry ride, and he seems like a perfect gentleman.
That's until she tells him she’s pregnant. He told her, “Yeah, I hear those hemorrhoids are a b***h.” Rachel leaves the date early to go buy $15 worth of chocolate bars. It might not have been the worst date she’s ever been on, but she probably expected more from the soap opera star.
7 Best: Gavin Mitchell
After returning to Ralph Lauren following her maternity leave, Rachel is surprised to find Gavin Mitchell (Dermot Mulroney) occupying her office. He took over her job responsibilities while she was away, and she is completely disgusted by him. However, when Rachel is often angry at men, it’s usually because she has underlying feelings for them.
In the season nine episode “The One With Phoebe’s Rats,” Monica hosts a birthday party for Rachel and invites Gavin. He arrives late, but he bought her a scarf. He explains that he has feelings for her, and they kiss on the balcony. It might not have been an official date, but Gavin was a very sweet, charming man.
6 Worst: Paul Stevens
In the show’s sixth season, Ross starts dating one of his college students, Elizabeth Stevens. At the same time, Rachel dates Elizabeth’s father, Paul (Bruce Willis). Paul disapproved of Ross and Elizabeth’s relationship, but Rachel made things better.
Things were going well between Rachel and Paul until “The One With the Ring,” when she asks him to open up to her. This unleashes an emotional breakdown as Paul starts sobbing uncontrollably. It’s awkward and that’s the last time she ever sees the crybaby.
5 Best: Rachel And Joey’s Date As Friends
In the season eight episode “The One Where Joey Dates Rachel,” Rachel and Joey (Matt LeBlanc) go on a playful date as friends while Rachel is pregnant. Joey is a perfect gentleman. He buys her flowers, lets her order whatever she wants, and they have meaningful conversations.
They have a great time together and it’s one of Rachel’s best dates, even if it wasn’t supposed to be romantic. At the end of the date, Joey realizes he’s developing feelings for her. This scares him, and it becomes an important storyline for the sitcom.
4 Worst: Rachel And Joey’s First Date As A Couple
Rachel and Joey may have had a great date as friends, but when they’re actually a couple during the show’s 10th season, their first date isn’t as fun. In the episode “The One With Ross’s Tan,” they decide to take their relationship to the next level. It doesn’t work out too well for them.
Rachel keeps subconsciously slapping Joey while he touches her. He fails to take off her bra. They realize that their friendship is too strong to take things any further, and they ultimately decide to stay friends.
3 Best: Joshua Burgin
During the show’s fourth season, Rachel dates Joshua Burgin (Tate Donovan), one of her clients at Bloomingdale’s. She has a crush on him the first time she meets him, and it takes a long time before they finally decide to date.
In the episode “The One With Rachel’s New Dress,” Rachel and Joshua have their first official date. They end up at his parent’s condo. They think they’re alone until his parents arrive. It might be an embarrassing date, but it seemed to work out well in the end because Joshua continues to briefly date her after that.
2 Worst: Steve, The Infertile Guy
In the season nine episode “The One With the Blind Dates,” Phoebe (Lisa Kudrow) sets up Rachel with Steve (Jon Lovitz). Phoebe knows Steve is a horrible match for Rachel, but she hopes this will convince her friend that Ross is the right man for her.
Steve is awkward and gives Rachel the creeps. He is bold, even telling her he’s infertile. He’s not funny and Rachel tells Phoebe that it’s the worst date she’s ever been on. That says a lot since she’s had some pretty awkward, questionable dates.
1 Best: Ross And Rachel’s Museum Date
Ross and Rachel finally become a couple during the show’s second season. Their first date was fun until they got back to her apartment. Every time Ross tried to be intimate with her, she started giggling. It wasn’t romantic.
Their next date was definitely better. When Ross had an emergency at the New York Museum of Prehistoric History, their dinner plans are delayed. However, they have a romantic date inside the museum’s planetarium. It’s sweet, innocent, and they’re finally intimate. So, this begins the story of Ross and Rachel.
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