The characters on Friends go on numerous dates during the popular sitcom’s 10-season run. Most viewers relate to the characters who are single, working, and having new experiences in their 20s. The “friends” are just like you.
For Monica Geller (Courteney Cox), she has more one-time dates on the show than other characters, excluding Joey (Matt LeBlanc). What’s not to like about Monica? She’s attractive, funny, a talented chef, and she’s hilariously quirky. She has her fair share of dating experiences. Some of her dates are successful, but most of them are cringeworthy. Let’s take a look at her best and worst dates.
Worst: Paul The Wine Guy
In the show’s pilot episode, Monica has been wanting to date “Paul-the-Wine-Guy” from the restaurant she works at for a long time. She finally goes on a date with him and she’s excited. Chandler (Matthew Perry) calls it “a dear-diary moment.”
The date seems to be going well. Paul confesses that ever since his wife left him, he hasn’t been able to be intimate with a woman in five years. This turns out to be a lie just to get Monica to sleep with him. Joey remarks, “Of course, it was a line!” Monica is upset and Paul was a grade-A sleazebag.
Best: Alan
In the season one episode “The One With the Thumb,” Monica starts dating a new boyfriend, Alan. He’s a great man and her friends love him — even more than Monica. He helps them win a baseball game. He convinces Chandler to quit smoking. He’s not a bad guy at all, but Monica doesn’t feel any “heat” between them.
They mutually break up. He admits that he liked Monica, but he couldn’t stand her friends. It would have been wrong for Monica to continue dating him just for the sake of her friends. She handles the breakup much better than everyone else.
Worst: Her Double Date With Joey
In the season one episode “The One With the East German Laundry Detergent,” Joey convinces Monica to go on a double date with him and one of his ex-girlfriends, Angela. Angela has already started dating a man named Bob, but Joey tells Monica that he is just Angela’s brother. You can imagine how confused Monica was when she saw Angela and Bob touching and kissing during the date.
It’s an embarrassing, awkward night, and Monica is upset with Joey for tricking her into this double date. However, it seems to work out in her favor when she starts flirting with Bob and he seems attracted to her.
Best: Mischa, The Interpreter
In the famous season three episode “The One Where Ross and Rachel Take a Break,” Phoebe (Lisa Kudrow) persuades Monica to go on a double date with her. Phoebe is dating Sergei, a diplomat from a foreign country who brings his annoying interpreter with him on every date. Monica was a distraction for Mischa.
While Monica has bad luck going on double dates most of the time, this was one of her best dates. Mischa is funny, charming, and he’s interested in Monica. They have a great time together. It might have caused a problem for Phoebe, but Monica didn’t care.
Worst: Fun Bobby
In the season one episode “The One With the Monkey,” viewers meet Monica’s on-again, off-again boyfriend, Fun Bobby. He’s great and lives up to his nickname, but in the season two episode “The One with Russ,” Monica realizes why he’s so much “fun.” He has a drinking problem. She convinces him to get sober.
Fun Bobby quickly becomes Ridiculously Dull Bobby. He’s a completely different character and Monica no longer has “fun” with him. She even has to drink before she sees him in order to find him more entertaining. However, Bobby breaks up with her to be with someone who won’t jeopardize his sobriety. That’s the last time she sees him.
Best: Richard Burke
Some fans are divided about their opinions on Monica’s on-again, off-again boyfriend, Richard Burke (Tom Selleck). For one thing, he’s twice her age and he knew her as a child. But putting the age gap aside, Richard is a great boyfriend. They genuinely love each other, and Monica is convinced he’s the love of her life while she’s dating him.
Their dates are fun and casual. They have a mature, compatible relationship. He’s sophisticated, and Monica grows to be a more stable adult. Even though their relationship didn’t work, it was adorable while it lasted.
Worst: Chip Matthews
Monica had a very different high school experience than her best friend, Rachel Green (Jennifer Aniston). She was overweight and Rachel was popular. Monica had a huge crush on Rachel’s boyfriend, Chip Matthews. So, when Monica bumps into Chip in the season four episode “The One With the Cat,” she goes on a date with him.
Monica didn’t know she was going on a date with the same Chip Matthews from high school. Yes, he never grew up. He still lives with his parents and he still works at the movie theater. He didn’t live up to her expectations. At the end of the night, she says that not only did she go out with Chip Matthews, but she got to dump Chip Matthews.
Best: Chandler Bing
Viewers were pleasantly surprised when Monica and Chandler started dating at the beginning of the show’s fifth season. They didn’t have to go on official dates to get to know each other because they were already best friends. They knew everything about each other, so their dates were sweet and romantic.
In “The One With All the Kissing,” the two share a romantic, candlelit bubble bath. It’s funny because they keep getting interrupted by Joey, who doesn’t know about their relationship. It might be a fun, awkward date, but it was the start of a wonderful romance.
Worst: Young Ethan
In the season one episode “The One With the Ick Factor,” Monica dates (what she thinks) a college senior, Ethan. The relationship is doomed from the very beginning. They have a romantic, fun date and end up sleeping together after he tells her that he’s a virgin.
After they have sex, Monica confesses her real age. That’s when Ethan tells her he’s a senior, but a senior in high school. Ick! Monica just committed a crime (sleeping with a minor), and she quickly says goodbye to that relationship.
Best: Pete Becker
Pete Becker is one of Monica’s longer relationships. They date towards the end of the show’s third season and there was nothing wrong with him. He was basically a millionaire who had a crush on Monica long before she felt attracted to him. However, she still dates him.
In “The One With the Hypnosis Test,” they go on a date. Monica thinks they’re staying in New York, but he flies her to Italy for authentic Italian pizza. Their relationship might not have lasted, but that has to be the best date Monica ever had.