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When Preston Calls Off His Wedding To Cristina — & Her Response Is "I'm Free"
Season 3, Episode 25 (2007)
Preston (Isaiah Washington) recognized that he wasn't Cristina's first choice, so he walked away from their wedding. Cristina, naturally, cried, but she was also relieved, shedding the necklace given to her by Preston's mom.
When Jo Tells Alex She's Married
Season 13, Episode 9 (2016)
Jo withheld the fact that she was married from Alex because she was afraid he'd try to attack her husband. The scene is shocking enough on its own, but the conversation also leads Alex to consider taking a plea deal and go to jail, eliminating the need for Jo to testify. (Jo is worried that if she names her abusive ex on the witness stand in Alex's trial, he'll track her down and possibly hurt her.)
That's definitely one way to end on a mid-season cliffhanger.
When Jackson Stops April's Wedding
Season 10, Episode 12 (2013)
Possibly the most shocking thing about this moment was the fact that it took ten seasons for Grey's to get an interrupted wedding. Jackson gets a lot of points for this romantic gesture, but also a bunch of demerits for using this moment not just to really ruin things for April's would-be husband, but for Jackson's actual wedding date, too.
When Cristina Almost Kills Alex
Season 8, Episode 12 (2011)
Sometimes the Grey's docs are more of a danger to each other than their patients. This isn't even the first time a doctor has gotten injured in the OR (see Derek's ex kind of stabbing him in the hand).