November 10, 2017 - Frazer Harrison/Getty Images North America more pics like this »
Alessandra Ambrosio And Jamie Mazur
Length of Engagement: 10 years

The supermodel got engaged to her businessman boyfriend in 2008, and they went on to have two children together before ending their engagement of 10 years in 2018.

In 2016, Ambrosio shared with Cosmopolitan about her reasoning for her long engagement, saying, "If I have been engaged to him for eight years, then it’s not my priority. I have a lot of things going on, and I haven’t gotten married because I’m so busy. I’ll think about that when I have time off."