Jill Duggar Credit: TLC John-David Duggar Jessa Duggar 6 of 14 John-David Duggar Jessa Duggar . Go to Comments . .. Jill Duggar Jill had her very first kiss in June 2014 at age 23 when she married Derick Dillard, her dad's former prayer partner. Two months after their wedding, Jill announced the couple is pregnant with their first child
Should Kids be Getting Married At 18? Jessa Duggar is 21 years old and she is courting Ben Seewald who is only 18. He is attending a community college and repairs windshields. Bob Duggar remarked on his show that they would probably hear wedding bells in a few months!