Kate McKinnon Bari Weiss Relationship: From Columbia Romance to Public Curiosity

It was either a punchline or a headline when they first met at Columbia. Even before the scene started, Kate McKinnon’s quick wit and elastic expressions made people laugh. Determined and keen-eyed, Bari Weiss was studying the texts that most students merely skimmed and posed questions that went two levels deeper than the syllabus called for. On the surface, their relationship might appear to be a curiosity. However, it was real—briefly romantic, occasionally chaotic, and ultimately formative.

Years later, Weiss publicly acknowledged their relationship in a Vanity Fair profile. It was brief but clearly genuine. It existed before podcasts could conjecture about motives and Twitter threads could analyze it. They were just two students sharing moments, sometimes in love, sometimes in disagreement, and always driven by ambition at a time when they were still learning how to speak and how loud to do it.

Even then, Kate was more interested in character than confession. Although she never shouted it from rooftops, her queerness was always present and woven into her being. Like trying on jackets at a vintage store, she inhabited personas on stage with assurance, humor, and occasionally a hint of melancholy. Weiss, on the other hand, would come to live on a completely different stage. One in which ideological battle lines, rather than punchlines, were at stake. One in which she would be both praised and ridiculed for expressing her true opinions, frequently in the same sentence.

Their paths clearly diverged after Columbia. With her notably lengthy and lavishly rewarded tenure on Saturday Night Live, McKinnon established herself as a comic institution. In addition to being incredibly witty, her portrayals of Ruth Bader Ginsburg and Hillary Clinton were also remarkably successful in transforming political clichés into late-night legends. McKinnon provided humor without ever trivializing the seriousness of the situation, even when the news was depressing—especially at that time.

Weiss’s path passed through institutions noticeably more quickly. She gained a reputation for challenging liberal consensus while still identifying as center-left, from The Wall Street Journal to The New York Times. Weiss presented herself as a contrarian in her writing, but not in rebellion but in earnestness. She was always in the crossfire of public debates, sometimes ahead of them and sometimes behind their subtleties.

Weiss had already established herself as a symbol of either free-thinking bravery or ideological opportunism by 2020, when she quit The New York Times, citing what she described as a “illiberal environment.” Shortly after, she started The Free Press, a Substack-based business that developed into a media brand driven by exclusive interviews, paid subscribers, and her trademark longform argumentation. She created a highly adaptable and unexpectedly profitable enterprise through strategic alliances and astute branding.

The renewed public interest in their past elicited no response from Kate. In a way, that silence was exactly right. Her voice is kept very private for someone who has dedicated her life to creating the voices of others. The only evidence of her alleged relationship with Jackie Abbott is a backstage photo here, a red carpet photo there. No statements, no posts. Just a gentle affirmation by staying present.

Their brief relationship is fascinating not because it happened, but rather because it doesn’t fit any preconceived notions. Being bisexual, loving both men and women, and not wanting to “trade on” that identity for points are all things that Bari Weiss has openly discussed. Depending on the listener’s political stance, that framing was both refreshing and frustrating, especially in our visibility-focused era. McKinnon, on the other hand, has never announced her coming out. During an awards ceremony, she once thanked Ellen DeGeneres, citing her as the inspiration behind her courage to be authentic. It was subtle, poignant, and remarkably unscripted.

Divergent attitudes regarding visibility, voice, and belonging are reflected in their stories and the space they currently occupy. Weiss frequently adopts stances that seem designed to elicit a reaction, but she maintains that she is motivated by principle rather than provocation. Rumors of her possible promotion to editorial leadership at CBS News have caused some concern in recent months. Entering the engine room of a legacy media company is a drastic change for a writer who was previously praised for questioning them from the outside. However, these unexpected recalibrations have shaped her entire career.

For her part, McKinnon appears to have found serenity in selectivity. Her post-SNL career has shifted toward low-exposure, high-impact projects, such as her iconic role as the quirky, unkempt Weird Barbie. Even though the role was humorous, it also alluded to a deeper thematic thread: characters who see the script, realize how ridiculous it is, and decide to stay. It had the feel of a wink. Maybe at us. At herself, perhaps.

As it is, their story lacks a clear takeaway and a dramatic arc. It wasn’t a tabloid or a tragedy. It was a relationship that began in college and developed into friendship; it is sometimes recalled with nostalgia and other times with perplexity. But in a time when meaning is extracted from every interaction, that simplicity seems more and more uncommon.

The way public memory handles their relationship is still intriguing. It reappears because it doesn’t quite compute, not because of salacious details. The bisexual journalist who plunges straight into politics and the queer comedian who stays out of it are briefly connected by their proximity and shared youth.

Both of them have influenced discussions in different ways; some have done so through argument, while others have done so through laughter. Even if they have grown apart, their stories continue to recur in late-night group chats, podcast mentions, and Reddit posts in subtle cultural loops.

Not because the story is relatable, but rather because it defies easy categorization, it is easy to imagine a younger generation, recently out, stumbling upon that Vanity Fair mention and feeling strangely seen. Maybe that’s what makes it valuable. Love stories don’t always have to end. Some merely add texture to already textured lives.