Is Jill Dillard (née Duggar) ready to leave her family’s rules behind and try a sip of wine? On Wednesday, February 5, the former Counting On star bonded with Ben Seewald‘s sister Jessica Lester over an Instagram post that featured a glass of the alcoholic drink and a few different kinds of cheese. The move shocked fans who know the Duggars steer clear of booze even after their 21st birthdays — and had some wondering if the mom of two was ready to do something new.

In the post, Jessica, 22, featured not just “wine [and] cheese,” but also a set of coasters that featured sweet sayings about the beverage. “Wine is the most civilized thing in the world,” read one paraphrased Ernest Hemingway quote. “Wine is constant proof God loves us,” read another from Ben Franklin. Using a hashtag, she dubbed herself a “wine lover.” Though Jill, 28, wasn’t exactly on the same page, she was happy to add, “Cheese lover over here! 😍”

Jill Duggar Bonds With Ben Seewald's Sister Jessica Over Wine and Cheese
Courtesy of Jill Duggar/Instagram

In the comments, some fans encouraged the TLC alum to branch out. “You should come to Oregon and try some of our amazing Pinot Noir,” one wrote. “Our climate produces lovely grapes.” A second chimed in, “Try the wine! You would be a fan!”

Jessica isn’t Jill’s only friend who considers herself a wine lover. The star’s new bestie, Rachel Virden, is also a big fan of the beverage. In her Instagram bio, she writes that she “loves Christ, [her] family, post-it notes and red wine.” Fans have been hoping that, by buddying up to their slightly more worldly pals, Derick Dillard and his wife will open themselves up to new experiences and new possibilities.

Jessica, in particular, seems to be a breath of fresh air for Jill. Though she and Jessa Seewald (née Duggar) are sisters-in-law, she seems to live by her own set of rules. In April 2018, she landed her own job as a police officer, and she’s not afraid to show a little skin on social media. In January 2020, she posed in just a sports bra and shorts as she and husband Phillips Lester flaunted their gym bodies. The couple even kissed before marriage, posting their PDA pictures online. Maybe one of these days during one of their hangs they’ll finally share a drink.

Have a tip? Send it to us! Email In Touch at