• Instagram Social Icon
  • Black Facebook Icon
  • Black Twitter Icon
  • Black Spotify Icon

© 2018 by Lake Shore Dive. Proudly created with Wix.com

  • Lake Shore Dive

Spotlight On: Gertrude aka Jessica Mascarenhas, poet and comedian

Updated: Jan 18



Poet and comedian Gertrude (Jessica Mascarenhas) will pull on your heartstrings with beautiful prose tangled in rich metaphors and vulnerability, then splash you with a cold dose of punchy wit and honesty. Laughter is her love language and something she seeks human connection with. Her work is funny, fresh, and smart.


Gertrude writes about topics that span the human experience from sexuality, racism, and sexism to family and waking up during colonoscopies-- she herself was diagnosed with Ulcerative Colitis/Crohn’s two years ago.


Above all, she wants to confront both her pain and the world's pain by bringing it to the surface and allowing us to laugh about it, which at the end of the day, feels entirely necessary when the weight of the world feels all too much to carry.


“I think as a depressed kid, you have two choices,” she says. “ One: You can let all the sad shit be felt as sad shit. Two: You can be like well, this sad shit is inevitable, so I might as well make a joke out of it.”



As a kid, Gertrude found comfort in the library, the books she read and the words that made them. Naturally she made the transition into writing. “Writing was a coping mechanism for me to make sense of the world,” she says.


The poems that she loved writing and performing were the funny ones, and eventually, she fell into the world of comedy--a world she says comes to her as second nature, programmed into her brain. Performing and making people laugh has become her medicine.

“The pain is there. It has already happened. I might as well try to make something out of it.”

Gertrude sees comedy as being one of the few platforms that allow people to digest real information and finds inspiration in people like Hasan Minhaj, who is doing the work in a way that feels authentic and true. “I look at him and I see myself and it feels so good to have someone as evidence to point at and say ‘Look, it’s possible. It’s possible to do what you love, look like you do, and make a difference,'" she says.



Gertrude lists a number of people who have inspired her, supported her, and have challenged her to be the best version of herself. She welcomes criticism and mistakes in exchange for growth and compassion. It’s these gentle reminders of our inevitable human flaws and the hurt we experience collectively and individually that allow for her to thrive.


“The pain is there. It has already happened. I might as well try to make something out of it.”


Follow Gertrude on Instagram to keep up with her recent work. Check out her personally curated Spotify playlist, and favorite things below.



Favorite part about the Chicago creative community? The Chicago creative community has been such a blessing. I don’t think I would’ve gotten into comedy until much later if I hadn’t felt so supported at open mics. It’s been much easier to get out of my comfort zone and perform about things I am nowhere near ready to talk about in everyday life. I was so nervous when I first started and if it seemed like people didn’t fuck with my work, I would take it personally. Now, I know it just means I can do better. That’s why so many dope artists come out from Chicago, because it’s a learning environment and we encourage each other to push harder and grow, because we know we’re capable.


Favorite TV show? My favorite T.V. show right now is Kim’s Convenience on Netflix. It’s the only show I watch that my dad actually likes. I haven’t heard him laugh at a show like that in awhile. It’s genuinely funny and heartfelt at the same time. I don’t know many comedy shows being written like that right now.


Favorite cocktail/drink?

Unfortunately, I don’t drink alcohol anymore but when I did it was definitely tequila. I drink a lot of tea now. My favorite one I make every morning is with mint leaves, ginger, cinnamon, jeera, and cardamom. If you have digestion issues, definitely try it.


Favorite Chicago artist?

I have a few favorite Chicago artists. Kennyflowers put out one of the best projects of 2019, JOAT.


One of my favorite comedians/poets/musicians who I learn so much from, especially about mixing genres is Jerwin Gabriel Santiago.


Jaz Star is my favorite singer in the Chicago scene.


One of my favorite poetry books is Citizen Illegal by Jose Olivarez. Also, Fatimah Asghar’s book, If They Come For Us, and her web series “Brown Girls,” and pretty much everything she does I’m in love with.


Saba was my artist of the decade on Spotify, (also in love with all of his music). Mother Nature is a rap duo I can’t stop listening to.


Some of my favorite Chicago poets right now who I’m lucky to be in the same spaces with are Davon Clark, Kwyn Riley, E’mon Lauren, Chima, and Raych Jackson.


The visual scene in Chicago is so talented as well. Painters, photographers, and artists such as ThoughtPoet (Isiah Veney), Jeff Koonz, Jai Kalondra, Swiper (Kayla), Kianni, and Mariah Harieon. We have so many great comedians like Sonal Aggarwal, Sandy Lee, Vikram Balaji, Sabeen Sadiq, Joel Kim Booster, and OF COURSE, Jaboukie Young, a young legend. I know this is a long list but I still feel like I’m forgetting so many people.


Favorite spot in Chicago? (can be a neighborhood, restaurant, bar, etc.) My favorite spots in Chicago are of course open-mic related. ISA Studios in Pilsen where Luya Poetry open mic takes place once a month was the first studio space that felt like home. The owner, Kielle, has become a dear friend of mine and I look up to her so much. I remember the first time I performed at Luya, I couldn’t stop coughing and she immediately cut up ginger and garlic for me and I was just chewing on it the whole night and that’s the only reason I was able to perform. The first time we met, she was just like, “I like you. I hear you do poetry. Do you want to feature at my next event?” She had never even heard me perform. I’ll never forget that. It was my first feature. The other one is Positive Space Studios where Respect The Mic takes place once a month. The owner, Melissa, is such an incredible woman. From the first time I met her, she has supported me and asks me to email her my poems. She even brought her two-month-old baby to the last open mic just because I was featuring! I feel so blessed in those spaces and to have strong women business owners in my life to look up to and who also support me.

"Spotlight On" is a bi-weekly series highlighting Chicago creatives with a twist. We share a slice of their stories and what they love, hoping to inspire and connect.


Words by Lolo Ramos