What to Know
When Josh Duggar decided to get married, his parents, Jim Bob and Michelle Duggar, were supportive of his decision to marry Anna Duggar (who was Anna Keller before she joined the famous reality TV family). But, according to Josh in one of his county jail emails to Anna in 2022 that was posted on Reddit, there were other women he could have chosen to court and marry instead of her.
Josh and Anna originally met at a homeschooling convention, which is nothing new for the Duggars. Jim Bob proudly talked about their kids making lifelong friendships and reuniting with friends at yearly conferences while filming 19 Kids and Counting. But, Josh wrote to Anna long after they were married and while he was locked up following his very serious charges, she almost didn’t make the cut.
Josh Duggar had options, apparently.

On 19 Kids and Counting, there was never really any question about Josh marrying Anna. He proposes to her during an early season and they sort of set the standard for holding hands after getting engaged and waiting until their wedding day for their first kiss and anything else beyond that. In the 2022 email, Josh hinted that things could have been different, had he gone with another one of the women that apparently had eyes for him.
“I am so glad that I married you and not anyone else!” Josh wrote to Anna. He added, “Especially the other two…that come to mind!”
It might not sound like much in terms of hot gossip involving the Duggars, but it does paint a picture of alleged matches that Josh might have had before or around the same time that he and Anna began courting. This was never brought up by the family before either, which is why it’s kind of a big deal now.
But he’s glad he chose Anna Duggar in the end.

After someone shared the email to Reddit, people commented about their surprise regarding Josh’s claim that he “chose” Anna over other women who he might have had interest in or vice versa at the time of his courtship with Anna.
“It’s just manipulation, used to gas a partner up ‘you are so much better/sweeter/more godly than X’ when he’s done something wrong,” someone wrote. “Because what it really means — if it means anything at all — is ‘that other woman wouldn’t have put up with me.’ Manipulators use praise very deliberately.”
Someone else added, “I’m sure they are feeling significantly more lucky than he is about not marrying him.”
The emails in the Reddit post also show Josh asking Anna more than once to send “sexy” photos to him while he was locked up in county jail. So maybe those mysterious other two women dodged a serious bullet?
There are theories about why Josh got engaged and married when he did.
@countingon2 #theduggars#theduggarfamily#joshduggar#jillduggar#jingerduggar ♬ 原創音樂 – countingon2
Some of those who have curiously followed the Duggars for years have speculated on why he married Anna at the young age of 20. Sure, Duggars tend to marry young as a rule and not as the exception, but some people believe Jim Bob and Michelle were eager to get Josh married off and out of the family home.
But Josh might have had a solid reason for allegedly choosing Anna. As one user put it on the Reddit post, “Anna is under-educated and has no critical thinking skills so I’m sure she completely believes this nonsense.”
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