It’s no surprise that the matriarch of the Kardashian-Jenner family, Kris Jenner, has some famous friends. Seriously, just last week she was seen cuddling up to Drake at his album release party. And now the famed momager is setting her sights on someone with reality TV stardom: former Bachelor star Ben Flajnik.

As you probably remember, the scruffy-haired Bachelor star is a winemaker from Sonoma, California and was formerly on Ashley Herbert’s season of The Bachelorette (Season 7). But he isn’t the only lucky guy that was hanging out with Kris at the vineyard. Don’t forget Jonathan Cheban, a close friend of the Kardashian family — he likes to tag along on some of the family’s adventures.

We wish we knew what Kris and Ben talked about on their little journey through wine country. We’re sure that wine was atop the list of conversation, but we bet the talk show host was imparting some wisdom on Ben. Perhaps she had a few words to say about him picking Courtney Robertson on his season. Any good mom would chastise him about that, right?

Are you surprised to see these two hanging out in wine country? Hit the comments and weigh in!

Carson Blackwelder is an Associate Editor at Wetpaint Entertainment. Follow him on Twitter and Google+!