When PokerStars ambassador Caitlin Comeskey talks about comedy and poker, she draws a clear connection between two worlds that ask for the same thing: courage. Speaking at the PokerStars North American Poker Tour 2025, where she served as emcee of the NAPT Comedy Night, Comeskey reflected on how the two passions overlap — and what each has taught her about fearlessness, failure, and finding community at the table.

“Oh man,” she said, “both of those pursuits, both comedy and poker, you have to be very comfortable with failure. You have to be willing to humiliate yourself and embarrass yourself. You can’t be afraid to look stupid.”

I think the most important part with being a poker ambassador is being fun to play with That lesson, she explained, applies whether you’re standing behind a mic or sitting across the felt. “You have to learn to trust yourself and sometimes you’re going to make a big hero call that is humiliatingly wrong, and it’s the same with comedy — you’re going to tell a joke that absolutely flatlines. I’d say it’s helped me be more fearless.”

Being “Fun to Play With”

When the topic turned to how comedy, theater, and improv shape her approach to poker, Comeskey didn’t hesitate. “I think the most important part with being a poker ambassador is being fun to play with,” she said. “My background in theater and comedy and improv has just helped me show up better at the table.”

She sees personality and presence as essential parts of the game — not just for entertainment value, but for what they bring to the player experience. “I’m not saying 100 times out of 100 I’m going to be the most fun player you’ve ever been with,” she laughed, “but my background in comedy and theater has definitely made me a good time, a good hang.”

Her self-awareness shows what makes her a strong fit for PokerStars. She isn’t pretending to be a statistical genius or a high-volume grinder. Her contribution is the human connection — the humor, empathy, and poise that can make even a tense table feel a little lighter.

An Untapped Market

Comeskey doesn’t just play for herself; she’s also vocal about why poker needs more women. “It’s very important,” she said. “It’s an untapped market. There are so many women, especially since less women are having children and less women are getting married. That means more women have disposable income to pursue hobbies like poker.”

If we’re going to run women’s events, then they need to have guarantees. That shift in lifestyle, she believes, creates an opportunity for poker to reach a broader audience. “I would love to see us figure out how to find that working woman with disposable income and bring her into the fold — show her all the different life skills poker can teach you,” she said. “Risk management, learning to be more fearless, and networking. It’s like a huge networking thing.”

For Comeskey, poker isn’t just a game — it’s practical training for everyday confidence. “It’s like why women should be playing golf,” she added. “To get around new faces. I would love to see more women in the game, not just because I’m tired of playing with boys all day, but because it really is a useful tool to working women.”

Shared Challenges, Different Experiences

Asked what challenges women face at the table, Comeskey pointed out that some of what gets labeled as gender-based actually overlaps with basic beginner struggles. “A lot of things that are hard for women who are brand new to poker are the same for men who are brand new,” she said. “They’re just beginner issues. People are going to pick up on the fact that maybe you’re more nervous at the table or less experienced, and so you’re going to play more passively, and they’re going to attack you more.”

But she also didn’t hesitate to name what’s different. “I do think that women probably on average are going to face a little bit more harassment and grumpiness from the absolute most miserable portion of the player pool than men will,” she said. “Getting othered, getting made to feel uncomfortable — I definitely think women experience that more, and it’s important that we talk about it so we can change it.”

Building Networks for Women

Since joining the poker world, Comeskey has seen improvement — especially through women-led initiatives like Victoria Livschitz’s Pocket Queens community. “One of my favorite things that’s come out in the last few years is the Pocket Queens group that Victoria Victoria Livschitz created,” she explained. “She was very successful in her line of work, got into poker, and climbed the ranks really quickly. She wanted to create a network and a platform that was mostly free and accessible for women who joined her study group and Discord.”

I didn’t know what to do, so I started barking at him like a dog, Comeskey praised the results: “All those girls are having amazing results, and they get huge names in poker to come and donate their time and educate women,” she said. “That’s a huge disadvantage that women can have in the game — because there are so many men, it’s easier for them to network, study, share travel costs. When you’re the only woman at the table, it’s harder to find that access.”

Her advice for tournament organizers is direct: “If we’re going to run women’s events, then they need to have guarantees.”

Content, Creativity, and the Internet’s Rules

One of Comeskey’s talents is poker content creation, but she admits that modern media demands can be frustrating. “We’re getting more younger people who speak Gen Z Internet,” she said. “My content definitely comes from a theater and comedy background and it’s targeted to a very niche audience. A lot of these younger creators are very fluid with the language of the Internet, the language of the algorithm.”

She admires their energy, but her creative instincts push in a different direction. “In a lot of ways that can be frustrating for me because I take myself very seriously as a performer and creator. I want quality, not quantity,” she said. “The current language of the Internet is like, you gotta post every day, produce, produce, produce. It can kind of feel soulless to me.”

A Performer at Heart

Comeskey is at her happiest onstage. “I love live performing,” she said. “That’s one of my favorite opportunities I’ve gotten working with PokerStars — they have Joe [Stapleton], a working touring stand-up comedian on their team, that puts on comedy shows at all the stops. I’ve gotten to do comedy at four stops this year. I got to headline in London. Live performance — that’s my secret sauce. That’s the thing I’m really good at.”

For Comeskey, comedy isn’t just a side project — it’s a creative force that keeps her connected to people and sharp in her poker ambassadorship.

Laughing Through Tension

Her story about a moment at the poker table in Tunica shows how humor can dissolve pressure, even in intimidating situations. “It was Day 2, so it was pretty intense and I was really short,” she recalled. “This one guy opened in early position, everybody folded out, but because he had seen me shove so much, he tabled his hand and said, ‘I would have called you.’ He stood up and pointed at me — it was really physically intimidating.”

“I didn’t know what to do, so I started barking at him like a dog,” she said. “I go, ‘You bark at me, brother, I bark back louder.’ It just fully diffused the situation. Everybody laughed, and we talked about it the rest of the week.”

That moment sums up Caitlin Comeskey’s approach to poker and life: humor, composure, and the courage to turn fear into laughter.