Throughout ten epic seasons of NBC’s Friends, Ross Geller dated plenty of women. Some were his colleagues, students, or just random women he picked from the coffee shop. Ross was also lucky enough to find love in beautiful, intelligent women such as Julie, and his ex-wife Emily.
But none of these worked. You know why? He was always Rachel’s lobster. Today we bring you every worst date Ross Geller has had.
Bonnie
Phoebe set up Ross with a woman named Bonnie after his break up with Rachel. Initially, Rachel was thrilled at the idea of Ross dating a bald girl. Once she saw the sexual chemistry between them, she wanted to break the two of them. At the beach house, Rachel nudged Bonnie to shave her head again. She confessed her love to Ross and almost got back together with him, at the time. Ross dumped Bonnie for Rachel, called a cab for her and she left.
Cailin
After Ross and Rachel are thoroughly finished with each other (for the first time), he brings a woman Cailin from work to Joey’s play. Ross is not ready to see another woman, let alone bring her as a plus one to a public gathering. It’s an awkward date, gives Cailin the least bit of attention all through the night. Instead, he spends time going after Rachel’s screamer date, Tommy. Cailin eventually walks out.
Mona
There’s nothing to pick on Mona for except that she and Ross never really had any chemistry. The timing wasn’t right for the two either. Rachel was pregnant with Ross’ baby, and Ross was divided between the woman carrying his baby and the woman he wanted to go out with. Ross ended up hiding Rachel’s pregnancy from Mona. Other than that, he freaked out over Mona’s idea of doing a holiday card together. Mona broke up with Ross once she found out Rachel had moved in with him.
Mrs. Altmann
This one doesn’t technically count as a date, but Ross did have something going with the librarian at his school. In “The One With The Rumor” we learn that, when Ross was in high school, he made out with a 50-year-old-woman one afternoon at the library. Mrs. Altmann needed some help with her word jumble, and one thing led to another!
Adrienne Turner
Ross and Chandler had a pact in college to not to date any woman from amongst the list of women such as Missy Goldberg, Phoebe Cates, Molly Ringwald. Ross broke the pact by making out with Adrienne Turner. He made sure that there was no way Chandler couldn’t learn about it. Little did Ross know that, at the freshmen year party, Chandler had witnessed the whole thing himself. It was just a one time fling, something that Adrienne was ashamed to tell people. Probably due to Ross’ unfortunate hair.
Michelle
Ross picked up a random woman, Michelle, to get back at Rachel after Emma was born. Their situation was complicated, they had a baby, and they lived together. Just when Ross had considered the teeny tiny possibility of him and Rachel getting back together, he saw Rachel kiss Gavin.
As an act of revenge, Ross tried to hit on every woman at the coffee shop and finally brought Michelle to the apartment. She went through his medicine cabinet and wanted to be Rachel’s new mommy! Wouldn’t blame Ross for shutting the door on her face.
Joan
Ross got himself a date with a woman named Joan who worked for Hugo Boss. He was all worked up about this date and took Rachel and Phoebe to decide his dress for it. A little mishap at the shopping trip led Ross to take one of Rachel’s bag. Ross wore a pink ladies sweater on his date with Joan. What do you do when your date and you, both arrive in the same clothes? You go your separate ways and never see each other again.
Woman Who Spent A Year In Mount Tibidabo
Ross went on a date with this woman because he was scared for his health. He was going through a dry spell and thus needed Joey’s help for a breakthrough. What did Joey do? Give him a make-believe story about backpacking across Western Europe years ago. Ross chose to narrate this story to his date. He began with hiking in the foothills of Mount Tibidabo outside of Barcelona. Turns out, the woman spent a year studying in Barcelona. She corrected Ross’s pronunciation of Tibidabo. The date went to dumps after that.
Elizabeth
Ross wore leather pants on this date. People like Ross don’t generally wear these types of clothes, but Ross did it to look good on a date. The date was going well, the pair were seated on a couch, but Ross was all burning up. He was dying from the heat as his pants began to shrink further with the sweat.
Ross then took an escape into the bathroom, pulled down his pants, and fanned his legs. But, once the pants were down, they couldn’t come up. Upon Joey’s advice, Ross tried lotion and powder to get the pants back on. Ross went home without pants, smeared in powder and lotion.
Kristen Leigh
The good Samaritan Joey decided to help a girl Kristen move in. He asked her out to dinner that night, and she immediately agreed for the second day, stating she had plans for the night. Kristen’s plans that night included seeing Ross. Technically, Ross and Joey were up against each other, and, after they realized it, they decide to compete against each other.
There was a spending limit of $100 that they set for the date. Ross broke it by buying her flowers worth $100, so Joey ambushed the two. Ross and Joey called each other names, and, before they knew it, Kristen was gone.
Kristen
Ross’ first date after he broke up with Carol didn’t go well. He had his reasons, Carol was carrying his baby and she happened to be at the same restaurant that Ross was at. Kristen was a lovely woman who lived in the same building as Ross. She even pretended to laugh at his lame dog years jokes. Unfortunately, Ross was into Carol the whole time. Before he realized it, she’d taken off.
Jill
What is with Ross and the Green girls? Ross dated Rachel’s sister, Jill, briefly. Jill’s father had sent her to live with Rachel to learn something from the one daughter he was proud of. Jill didn’t learn jack. Instead, she went shopping for Pashmina and apartment pants. Jill dolled up for her date with Ross to make Rachel jealous. Ross called the whole thing off after sensing Rachel’s discomfort. It would have also thwarted any future possibility of them getting together.
Cheryl
Cheryl didn’t need a date, instead, she needed the department of sanitation at her place. Even though she was incredibly hot, Ross couldn’t get past her messy, dirty apartment. The whole thing ended, despite Ross offering his apartment for dates. Cheryl said his apartment smelled weird.
Janice
Who knew Ross and Janice would have a fling? Ross dated Janice during a tumultuous period in his life. Ross thought his and Janice’s situation was similar, as they both were single parents and divorced. In a hilarious twist of events, Janice ended up breaking things with Ross because she couldn’t hear him whine too much.
Hillary
Ross whitened his teeth for his date with Hillary. Only, he left the gel a day longer than he was supposed to. Monica tried her best to hide his teeth, used a highlighter on them, and put make on him. On the actual date, Ross hid his teeth from Hillary. He made weird noises for yes and no, put his hand in front of his mouth, used bread to cover his teeth. The two took things to the couch and Hilary dimmed the lights to black. Ross’s insanely white teeth shined in the dark, and that was that.
