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Best of The Bachelorettes

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Round #1, Matchup #4
Matchup Date: ?
Jen Schefft

Jennifer Ann "Jen" Schefft was a contestant on the 3rd season of The Bachelor where she got engaged to Andrew Firestone. They broke up after a few months.

She was later chosen for the 3rd season of The Bachelorette. Jen originally rejected both Jerry Ferris and John Paul Merritt in the finale. During the first live final rose ceremony, she chose Jerry, an art gallery director, over Meritt. Ferris proposed to Schefft, but she rejected his proposal, stating that the chemistry was not there.

Schefft ultimately married Chicago public relations executive Joe Waterman in May 2009. They have two daughters, Mae Elizabeth and Charlotte Grace.

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Emily Maynard

Emily Maynard Johnson was a contestant on the 15th season of The Bachelor, where she got engaged to Brad Womack. She was later chosen as the bachelorette for the 8th season of The Bachelorette.

Emily has a daughter, Josephine Riddick "Ricki", with her ex-fiance Ricky Hendrick. He died before their daughter was born. She chose Jef Holm on The Bachelorette and accepted his proposal. Maynard and Holm ended their relationship in October 2012. She married Tyler Johnson in 2014 and they have a son, Jennings Tyler. They welcomed a second son, Gibson Kyle, on September 16, 2016. On August 29, 2017, they announced that they are expecting their third child in a few weeks. Their third son, Gatlin Avery, was born on November 12, 2017.

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