Kate McKinnon and Bari Weiss Dated in College — A Look Back at Their Relationship

The world is full of couples who, on paper, might not make sense to the outside world. From Timothee and Kylie to Pete Davidson and everyone, sometimes we just don't get it. There are romcoms built on the idea of the wacky couple that doesn't fit until the last five minutes of the movie.

Even teen stories do this. We're looking at you, Bella and Edward. Sometimes you have to become a vampire in order to make it.

All of the internet and most of social media have somewhat prepared us for the possibility of a totally random pairing. If you want to get dark, a lot of convicted killers found love by way of a determined person who didn't mind writing letters and possibly never touching. We have true crime documentaries to thank for this knowledge.

Despite all of this, how are we still shocked by the idea that Saturday Night Live alum Kate McKinnon once dated Bari Weiss, co-founder of The Free Press?

Both Bari and Kate play their cards close to their chests when it comes to this particular relationship, if you can even call it that.

In 2019, Bari was profiled by Vanity Fair, who asked about the journalist's dalliance with one of SNL's funniest players. After high school, Bari spent a year in Israel, where she discovered a lot for musical theater at Hebrew University.

When she got back to the United States, Bari decided to attend Columbia University, where she met and fell for Kate. Evidently, this relationship was an on-again, off-again situation that resulted in a lasting friendship.

That's all Bari has ever said about Kate, and as far as we know, Kate has never commented on her time with Bari.

Bari and her wife Nellie Bowles co-founded The Free Press in 2021 following her departure from The New York Times. The breakup between Bari and the legacy media company was not amicable, as the former accused the latter of fostering an environment ripe with bullying and stringent woke thinking. Some good that did come from Bari's time at The Times, was meeting her wife Nellie.

In a post to X (formerly Twitter) from February 2025, Bari celebrated seven years with Nellie, whom she met after pitching her an idea. Nellie was a tech reporter and Bari thought she would like to know that conservatives were being shadow-banned on social media. Bari did not think much would come of that, and Nellie read the email to an amused group of colleagues.

Still, Nellie was intrigued, so she told her editor she was going to meet with Bari to "set her politics straight."

In March 2018, they met for coffee, and as Bari told American Jewish University, for Nellie, it was love at first sight, but for her, the spark wasn't there just yet. Bari revealed that Nellie wasn't the kind of person she thought she was looking for, but Nellie remained vigilant for the next six months.

The two married after Nellie converted to Judaism, and they now have a daughter and a son.