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Kaitlyn Bristowe And Shawn Booth
Length of Engagement: 3 years 

Kaitlyn Bristowe and Shawn Booth of Bachelorette fame were engaged for three years before their split in late 2018. The two liked to poke fun at their long engagement, where in 2017, Bristowe celebrated their two-year mark with a Instagram post that read, "Cheers to the longest engagement ever. I like that we don’t feel pressure, I like that we have taken our time, I like that we still don’t have a date set, and I kind of like you.”