Before Michael Scott got married to Holly Flax, the woman of his dreams, he dated quite a few women who ended up either breaking his heart or just not being the right fit for him. His relationship with Jan Levinson was beyond toxic as she tried to manipulate him and control him emotionally and financially. His relationship with Helene Beasley, Pam’s mom, ended when he found out how old she was.
His relationship with Donna ended when he found out that she was secretly married to a baseball coach -- And he really wanted his relationship with Donna to last. He just wasn’t willing to compromise his morals. Before finally settling down with Holly, Michael spoke up a lot about heartbreak and love lost. Here are some of his most memorable heartbreak quotes.
10 When He Was Tired Of Being Single: "I Want To Play Ball With My Kids Before I Get Too Old. And Before That Happens, I Need To Get Laid. And, Before That Happens I Need To Be In Love."
Michael Scott was definitely tired of being single when he told everyone in the office about his relationship woes. He revealed that it was important to him to be young enough to play ball with his kids but he knew that in order to make that happen, he had to be in love with a woman first.
Starting a family was always one of his biggest dreams and aspirations. Individuals who are still single at an older age can easily relate to this quote.
9 When He Was Single On Valentine's Day: "Just About Everyone In This Office Is Single Right Now. Including Me. And Everyone Is Experiencing An Incredible Amount Of Emotional Pain. Especially Me, Because Of My Great Capacity For Emotion."
When Michael Scott was single on Valentine’s Day, he absolutely hated it. He wanted more than anything to be in a loving and lasting relationship but instead, he found himself alone on the one day of the year that focuses on love, romance, and relationships.
He vocalized his sad feelings by describing the emotional pain that he and his single coworkers were enduring. He was probably feeling a bit more dramatic about it than his coworkers.
8 When He Wanted To Be Set Up On A Blind Date: "No Question About It, I Am Ready To Get Hurt Again."
When Michael Scott wanted to be set up on a blind date, he asked everyone in the office to write down the name and number of an eligible bachelorette.
He had just gone through a breakup but he openly admitted that he was ready to get hurt again. The fact that he looked at a new opportunity for love in such a detrimental way speaks volumes about where his mindset was at the time. He ended up going on a failed blind date with Pam's landlady.
7 When He Found Out Donna Was A Cheater: “It Was Either Living With Myself Or Being Happy. And I Picked... The... Former.”
When Michael Scott found out that Donna (his arcade-owner girlfriend) was actually married to a baseball coach, he was absolutely heartbroken and devastated by that.
He had to make a difficult decision… Compromise his morals and stay with her for the pleasure, or walk away from the relationship keeping his dignity and self-respect and talked. He chose to be an honorable man, even though he had real feelings for Donna.
6 When Carol Dumped Him: "It Hurts My Heart. It Hurts My Stomach. It Hurts My Arms."
When Carol dumped Michael, he was not okay with it whatsoever. He laid on the floor next to Pam’s desk and complained about how he was in physical pain. It is true that heartache can cause physical pain in some instances because it is so difficult to heal from emotional turmoil.
Carol dumped him right around the holidays too which made it even worse and harder to deal with. His relationship with Carol came to an end because he photoshopped a picture of himself into a photo of her and her kids with her ex-husband which was obviously way too cringe-worthy.
5 When He Talked To Pam About Holly: "I Can Tell You Confidently That It Is Not Gonna Be Okay."
When Pam Beesly tried to talk to Michael about Holly she told him that things were going to be okay and he responded by telling her that he confidently knew things were not going to be okay. He was heartbroken at the fact that Holly was still in a relationship with AJ because he wanted to be with her so badly.
It was at this moment that Pam informed him about Holly's ultimatum with AJ which gave Michael a spark of hope. Pam was thoughtful and considerate for giving Michael this piece of information.
4 When He Wanted To Dump Jan (The First Time): "I’m Unhappy When I’m With Her."
Michael admitted to Pam, Karen, and the rest of the women in the office that he was unhappy when he was in his relationship with Jan Levinson. After watching the "Dinner Party" episode, it became clear to everyone that Jan was extremely manipulative and toxic.
Prior to seeing that dinner party episode, the only insight viewers really got into how toxic his relationship actually had become came from him describing how bad things were.
3 When He Was Dumping Helene While Thinking About Holly: "Honestly, For A Long Time, I Thought I Was Going To Grow Old With Holly."
The entire quote says, "Honestly, for a long time I thought I was going to grow old with Holly. And then I met Helene. And she is great and she already knows and has done everything that I have ever wanted to do and can tell me about it. But, I think I want to do those things myself."
Hearing him reflect on his relationships with both Helene and Holly was sad to see but also very truthful. He wanted to be with Holly and was uncomfortable about Helene's age.
2 When He Hosted The Lonely Heart Circle: "Well Here We all Are. Alone But Together. No Flowers For Us. Relationships? We Don’t Need No Stinking Relationships."
When Michael insisted that all the single people in the office sit around in a circle and tell stories to each other about their biggest heartbreaks, he started things out with this quote. This particular quote from Michael Scott comes off as very bitter but that is because he definitely felt very bitter when he made this comment.
He wanted to pretend like relationships weren’t important to him but it was blatantly obvious how desperately he wanted one more than anything.
1 When He Found Out Holly Was Still Dating AJ: "I Guess There Are Just Some People Who You Stay Together With When You Transfer, And Some People You Don’t. And That’s Just The Way It Is."
Ultimately, viewers know that Michael Scott ended up getting married to Holly Flax. Prior to their reconciliation, she was in a long-term relationship with AJ. When she told him she was with AJ, Michael felt really terrible about it. He was confused about why she was willing to stay in a long-distance relationship with AJ but she wasn’t willing to stay in a long-distance relationship with Michael.
After he opened up about how he felt, it led to them having a conversation about getting back together. Eventually, they got engaged and eventually, they moved to Colorado together where they got married and started their own family.
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