All 10 Michael Scott's Love Affairs, Ranked From Toxic To Real Love

Michael Scott has had his fair share of romantic passions throughout the Office series. From awkward encounters to heartfelt connections, Michael's love life has provided plenty of laughs and cringe-worthy moments.

Here are all 10 of Michael Scott's love affairs, from the most toxic to the most genuine.

10. Jan Levinson

Here she is, Jan Levinson-Gould — the most horrible self-centered partner you could ever have. Jan and Michael's on-again, off-again relationship was a rollercoaster of emotions.

Jan's manipulative and controlling nature often clashed with Michael's desire for a stable and loving partnership. Michael always deserved better.

9. Donna Newton

From enemies to lovers. Michael's relationship with Donna, a married woman, was undoubtedly one of the most toxic of his love affairs.

Although their affair had a spark and passion, nothing good could come from something built on deception and infidelity. But being the other man certainly boosted Michael's ego.

8. Nikki From Benihana

After another heartbreak, Michael's co-workers decided to cheer him up and took him to a local bar. After too many shots, he invited Nikki, a waitress from Benihana, and her friend to the Dunder Mifflin Christmas party.

He ended up not being able to tell his date apart from her friend and marked the right one with a marker. A truly iconic moment.

7. Katy Moore

A purse saleswoman and the only vendor Michael ever let inside his office. Katy's charming looks immediately developed Michael's infatuation.

But he was not the only one who laid his eyes on her. Jim Halpert stole a possible future girlfriend from under Michael's nose, leaving him crushed (but luckily, temporarily.)

6. Marie The Concierge

Michael's one-night stand that helped him get over his other breakup. He met Marie on a business trip to Winnipeg, and even though he ended up getting kicked out of her room, the experience was more pleasing than toxic.

At least for one of them.

5. Landlady Margaret

After several unsuccessful blind dates (do you recall the one with Julia, Pam and Jims' friend, where Michale pulled out his Date Mike alter ego and ruined everything?) Michael decided to shoot his shot again with Pam's landlady, Margaret.

They could have actually worked out together, as Margaret turned out to be a very nice woman, but Michael was a complete douche about her looks and age, so they understandably never met again.

4. Pam's Mom

The relationship that we never saw was coming. Michael and Helene, Pam's mother, started dating after their one-night stand at Phyllis' wedding.

Though this love affair was inappropriate and strained his friendship with Pam, the couple seemed to be very happy together. We wish Michael never found out Helene's true age…

3. Glove Girl

An unknown woman Michael met while donating blood in the Dunder Mifflin parking lot. They comforted each other with jokes and seemed to have a nice conversation, but Michael passed out and when he woke up, the mystery girl was gone.

The only thing she left behind was her glove, and Michael spent the episode looking for this girl, even setting up an event for her, but she never showed up. A promising love line that we never got to see.

2. Carol Stills

Carol was the realtor Michael briefly dated. Despite their eventual breakup, their relationship was based on genuine affection and shared interests.

They had fun together and genuinely enjoyed each other's company until Michael scared her off by proposing to her too soon. It's even more funny when you find out that Steve Carell's real wife, Nancy Carrell, played Carol.

1. Holly Flex

Holly, Michael's soul mate and the only endgame we would accept. She brought out the best in him and showed fans the real Michael.

Their quirky and genuine connection made them a perfect match. Though different circumstances and misunderstandings tried to keep them apart, true love will always find its way back.