It's nerve-wracking enough to pop the question to your S.O., but if you happen to be a Duggar, there's another step you have to go through first: the courtship proposal. See, ICYMI (and bless you if you're out of the loop) the fundie family is really big on the side-hug life and love to put a ring on it before you even get to know each other. But before you can even have that non-relationship and eventually get married, you have to go through Jim Bob Duggar…and ask him if that special someone can finally go on chaperoned dates with you.
Because it's absolutely so farfetched that there would even be such a garish step between getting pre-engaged, we decided to look at all the most hard-to-watch Duggar pre-proposals. Some, like Jinger and Jeremy's, are relatively harmless, like watching a sort-of-sweet promposal…between two people in their 20s. Others, like Jessa and Ben's supervised (and video recorded) courtposal, is the stuff of cringe legends. And some, like Josh and Anna's, didn't really happen on screen so we didn't have to witness it. Lucky for us.
Best of all though, most include a slightly uncomfortable convo with none other than Daddy Duggar himself, and that's worth the price of admission. Scroll down to see all the oh-so-awkward Duggar courtship proposals.
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