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On June 23, 2008, Josh went to Florida to propose to Anna, following her father's guidelines that she not get engaged until she was twenty years old.
After proposing, Josh and Anna (along with two of Anna's sisters, Priscilla and Susanna who served as chaperones) drove back to Arkansas so that Anna could spend time with Josh's family.
During this appearance, Anna told host Meredith Viera that she had suffered a miscarriage before this pregnancy, saying "It's very hard to go through the excitement of finding out we were expecting a little one and then losing it.
One thing that really helped was thanking God, thanking him in the good times and thanking him when things don't go the way we expected them to ...
This visit is featured on the 17Ka C episode "Duggar Dating Rules", where Josh and Anna, along with some of the Duggar siblings, discussed their rules for courtship and engagement.
These rules included always having chaperones when the couple was together and saving hand-holding for engagement and any further physical contact for marriage.
They are a second-generation fundamentalist family, as both Anna's parents and Josh's parents are practicing members of the Institute of Basic Life Principles.Growing up in a large family, and Joshua in a mega-family, you learn so much more.I think a large family helps you prepare for life." On April 13, 2009, Josh and Anna announced that they were expecting their first child."I am very excited and am learning new ways every day that I can be there for my wife.I thought that she would be the only one going through the emotions of pregnancy, but I'm right there with her," Josh said in their statement.