Phoebe was right. The collective dating record of every member on Friends reads like a who’s who of human crap. Throughout the course of Friends, each member had her fair share of bad dates. The mother hen of the group, Monica was no exception. She may have been the first one to settle into a stable marriage with the love of her life, but hey, it wasn’t a straight path.

Monica dated a range of men, perhaps the most diverse out of the group, her father’s best friend and his son, a childhood crush, a millionaire a poet, a manchild. For the purposes of this article, we’ll count every worst date that Monica has had, till she found her soul mate, her best friend, Chandler.

Alan

“I personally could have a gallon of Alan,” said Chandler. Turns out, Alan doesn’t feel the same way about Monica’s friends. Monica doesn’t feel the same way about Alan either. There’s nothing much to pick on Alan, except he didn’t like any of the guys or the gals, he just pretended to like them very much and had immense control over them. So much so that he talked Chandler into quitting smoking, ruled at baseball whilst the five rallied around him. “First base Alan, second base Alan..”

Since Alan is Monica’s date, it would only hurt if she continued to see him just for the sake of her friends. She ends the relationship with Alan and handles her gang’s heartbreak instead.

Pete

Other than Pete’s strong urge to become the ‘The Ultimate Fighting Champion’ and buying Monica’s love continually, he seemed a pretty decent date.

Here’s the thing: even if we forgive Pete for suddenly wanting to beat himself to death in the fighting ring and lecturing Monica for not being able to understand “a man’s goal,” there are a lot of weird things happening between the two. For starters, he writes Monica a $20,000 cheque for a tip and buys her a restaurant. Money can’t buy love, Pete.

Fun Bobby

Contrary to his name, Fun Bobby ceased to be fun as soon as he gave up his drinking. The guys were right, every story of Bobby began with how wasted he was or how bombed he was. It’s also revealed that Monica and Bobby dated each other in the past, so they are basically an on-and-off couple.

Monica counseled Bobby into quitting drinking. But once he was sober Bobby, he was just dull. Hence, after countless boring dates, Bobby dumps Monica by accusing her of having a drinking problem. Nice try, Bobby!

Chip Matthews

Do you know how Monica really wanted to go out with Chip Matthews in high school? Well, she actually went out with Chip Matthews in high school. Not only did she go out with him, but she also got to dump him…

In “The One With The Cat,” Monica runs into Chip at the bank. He asks her out on a date and she happily agrees to it, thinking she somewhere owes it to the girl who always wanted to go out with the most popular high school boy, much to Rachel’s discomfort. Monica is quick to realize that Chip hasn’t grown up a bit, and he pretty much acts like a high schooler. The highlight of the date is when Chip tells Monica he still works at the multiplex for free popcorn and candy and lives with his parents. Yikes!

Young Ethan

How young is young Ethan? So young that he’d need his parents’ permission to spend the night out. Young Ethan and Monica’s relationship was based on lies. Monica told Ethan she was 22, while she actually was 26. As for Ethan, he was in high school but claimed to be a senior in college. Icky, right?

In “The One With The Ick Factor,” Monica briefly goes with Ethan. He’s pretty charming, well mannered, and cracks good jokes for a high schooler (gun-point is actually a place where crimes happen). Both of them reveal their real ages to each other after he stays the night. Ethan’s lie has made Monica a felon in 48 states! She ends the relationship the next day considering she didn’t want to be taken as a woman who hangs around with shiny guys named Chad.

Jean Claude Van Damme

Rachel and Monica spot the movie star, Jean-Claude Van Damme at a movie set. Turns out Monica is totally obsessed with him since Time Cop but doesn’t have the guts to walk up to him and ask him out. Instead, Rachel walks up to Jean-Claude Van Damme to get Monica a date. He appears more interested in Rachel and asks her out, instead.

Later, Jean-Claude Van Damme makes the exception to go out with Monica. It is only because Rachel has told him Monica’s dying to have a threesome with him and Drew Barrymore. On the date, he walks ahead of her to lay some apparent ground rules that Drew has for threesomes, leaving Monica utterly shocked and embarrassed.

Julio, The Poet

Monica and Julio work together at the Moondance Diner. Monica is encouraged by a co-worker to get it on with Julio. The two casually pick a conversation one night over the book, ‘The Flowers of Evil’ by Baudelaire. She learns that he’s a poet who writes about things that move him, such as the shadow of a tree, a child laughing, and Monica’s lips.

Julio accidentally leaves behind a poem he wrote in the middle of a date night with Monica. Chandler, Phoebe and Joey read out the words from the poem, ‘The Empty Vase- The Succulent Beauty’. Monica is described as an empty vase in the poem. When she confronts him about it, he says the poem isn’t just referring to her, but to all American women!

Monica hires a string quartet to get back at Julio in the end. “You are just a butt-munch, no one likes a butt-munch!”

Timothee Burke

Monica has the best luck with eye doctors, only they are father and son. As if dating Dr. Richard Burke wasn’t creepy enough, Monica went ahead an invited Dr. Tim Burke, his son for a Thanksgiving dinner.

Monica and Tim are introduced to each other in a meet-cute. She’s accidentally hurt her eye and Timothy is the on-call doctor at the clinic. Going out with the father and followed by his son, is super creepy. And that’s why the two agree not to see each other after they share a kiss post-Thanksgiving dinner.

Richard Burke

Say what you will, Richard Burke is the worst romance written for Monica’s character in Friends. Richard was introduced to audiences in Season 2, and it divided the fan bases into two halves immediately. Some may say he was Monica’s first long-term relationship, they had great bonding, chemistry, and understanding. But let’s not overlook the fact that Richard was Monica’s dad’s best friend. Let’s for a moment not hold Richard’s age against him. Let’s think in terms of appropriate behavior with the kids who grew up on your block.

Richard is a friendly neighbor, Monica’s dad’s best friend, Jack Geller dad still plays golf with him, Monica peed in his pool as a kid. Need we say more?

Paul, The Wine Guy

“You are going out with the guy, there’s gotta be something wrong with him.”

Meet, Paul the wine guy, Monica’s not-a-real-date. Paul is someone Monica has been waiting to date for long. She’s very excited to see him, so much so that, Chandler calls it, “a dear-diary moment.” The date goes well, the two have a nice conversation, and Paul spends the night at her apartment. The next morning, Monica learns from a co-worker that Paul’s lied to her about not being able to perform sexually since his breakup.

Just as Monica thinks, why someone would do that. Ross provides her with the answer: to get you into bed!