What to Know
There’s no way Josh Duggar is coming back after these emails. The emails he wrote and received in 2022, prior to leaving county jail for federal prison, keep coming out and making their way into social media. The downside for Josh and Anna Duggar is the amount of dissecting people are now doing with the emails. The upside for those who are still morbidly curious about the former 19 Kids and Counting stars is that things keep getting juicier.
In one email shared on Reddit, Josh corresponds with a woman by the name of Angel who was Anna’s new bestie at the time and the wife of one of Josh’s friends in jail with him. Josh even calls Angel Anna’s “BFF” in an email to her. He also discussed swimwear, something more risqué for Anna than the modest swimwear she once wore with him, and coming up with creative emojis to send sexy messages to their respective spouses. In a way, it’s what you’d expect from this particular Duggar.
Josh might have Angel to thank for the sexy photos of Anna.

Before Josh was found guilty on charges related to child sexual abuse material, he faced a cheating scandal involving the extramarital affair website Ashley Madison. So the idea of him chatting it up with another woman can only spell trouble. Though in one email, Josh discussed swimsuits with Angel, seemingly in an attempt to make sure she helps Anna find something revealing enough to take some selfies on and send to him.
“Anna rocked that homeschool swimwear lol, but I prefer a little more risqué when we have privacy (which isn’t often!),” Josh wrote. “She said you talked about ’emojis’ lol its crazy us desperate guys that miss our wives! Thanks for encouraging Anna and I am so thankful you both have each other — you are BFFs.”
In response to the emoji comment (Josh’s emails to Anna include lots of suggestive and downright strange emojis in an attempt to woo her, it seems), Angel joked that it’s “how homeschoolers get creative.” Apparently, it’s something her own husband does, so maybe Josh learned it from him first.
The Redditor who posted about the emails between Josh and Angel wrote, “I doubt this is fundie approved correspondence with someone else’s wife!”
Someone else agreed, “This is super weird.”
Josh seems to try and test boundaries with Angel.

Whether Josh’s emails with Angel were innocent on her part, or even his, they don’t look great. He seems to try and see how much he can say and what she will say in response to either deflect or encourage him. At least, it seems that way from some angles when you look at their correspondences.
“It reads as boundary testing to me,” someone wrote on Reddit. “Angel is just being friendly and joking about their swimsuits originally and then Josh makes it weird by talking about what he prefers which is totally inappropriate.”
Another Redditor commented, “I think we can safely establish based on his past history that [Josh] has no respect for or conception of boundaries, period.”
Yeah, that’s fair enough. Did anyone really expect this particular offender to be entirely appropriate and respectful with a woman involved?
People think Josh is likely to reoffend based on the emails.
@duggar.family #duggarfamily #kendraduggar #josephduggar #viral #foryoupage ♬ original sound – Duggar Family
Josh maintained his innocence after his conviction. But, according to users in that Reddit thread with those emails between Josh and Angel, he seems to be likely to reoffend, if given the chance. Maybe that isn’t fair to speculate on, but no one is really worried about Josh’s feelings right now, come on y’all.
“After reading so many of these emails, I honestly believe Josh is highly likely to reoffend once outside bars,” a user shared in the comments.
Someone also pointed out, “He’s also going to spend 10+ years with other sex offenders who probably are more worldly and have been predators longer than Josh. I don’t think he’ll last that long on the outside w/o breaking his parole. I hope his siblings stay cutting him off once he gets released.”
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