The drama that unfolded around Mesnick wasn't new. He appeared on "The Bachelorette" during the 2008 season as a contestant vying for the attentions of bachelorette DeAnna Pappas. He made it to the final two.
Pappas would later claim that she, too, had made a mistake in choosing professional snowboarder Jesse Csincsak over Mesnick during the season 4 finale.
And during the 2007 season of "The Bachelor," Brad Womack didn't choose either of his two finalists during his final rose ceremony.
In fact, in all the incarnations of the show, only one couple has made it down the aisle. Trista Rehn, who came in second on the first season of "The Bachelor" and was the original "Bachelorette," married her pick, Ryan Sutter.
Today, the couple has two children.
Happy endings would also seem to be in store for Mesnick, Malaney and Rycroft.
"Everything works out the way it should," Rycroft said, when announcing her engagement.
Mesnick said "fate has taken us all to a unique place right now."
CLICK HERE to visit Mesnick's Web site Jason's Place, an online community for single parents.
ABCNews.com producer Imaeyen Ibanga contributed to this report.