Maggie Losek would do anything to hear the clink of her wine glass against her best friend’s one more time.
What was once routine became the thing Losek missed most. Jillian Flynn died in November, following a battle with breast cancer. Even though she can’t pour two glasses and settle on the couch with Flynn anymore, Losek has a new way of keeping her close.
She got a tattoo of Flynn etched on her arm, goofily staring down the camera in sunglasses and a visor.
“It’s on the back of my right arm — now every time I go to have a glass of wine, it’s like she’s having a glass of wine with me,” Losek says.
Losek and Flynn both lived in Chicago, but met while traveling in Argentina. A mutual friend introduced them after saying for years the two would click. After a dinner prepped by Losek, they became fast friends, bonding over their French bulldogs.
“We were just chatting and drinking wine, and that was sort of the beginning and the end of everything,” says Losek, 33.
Losek and Flynn worked together in health care marketing, and Losek spent most evenings with Flynn and her husband, David Gray. One night, David came through the front door and found the two women performing “A Whole New World” from the movie “Aladdin.”
“He just looked at us and turned around,” Losek says. “She was always down for a good time, and she didn’t care what everyone else thought.”
Flynn, a huge Chicago Bears fan with a sharp memory and knack for planning parties, was the star in many of Losek’s favorite memories. Her tattoo inspiration came from wandering through Target after sharing a few glasses of wine. Flynn put on a visor and dubbed herself “Gayle,” to Losek’s booming laughter. “Gayle” was a fictional character, Flynn’s “drunken alter ego” that became an inside joke between them.
After many fun nights with Losek in Chicago, Flynn, her husband and son moved to Arizona. In December 2023, Flynn found a lump on her breast that was diagnosed as cancer. Despite multiple rounds of chemotherapy, it progressed to stage four. Flynn was 42 when she died Nov. 30.
When Flynn was dying, Losek tried to book a flight to say goodbye in person, but Flynn’s decline was too quick, she says. She had to tell her friend she loved her and say goodbye over the phone.
Losek told Flynn she would take care of her husband and son, whose first name is Flynn (he has his father’s last name). She died soon after that conversation.
The following weeks were dark and dominated by grief for Losek.
“I totally shut down, it felt like my world had shattered,” she says. “She was such a close confidant and somebody I could always go to for memories. … It felt like everywhere I looked, I found something I needed her for.”
In those throes of grief, Losek decided Flynn should be immortalized with tattoo ink.
“I wanted to be able to see her face every day,” Losek says. “That picture in particular made me laugh so much, and I thought she would have found it really funny, too.”
So, Losek contacted Kirstie Lewandowski, who goes by Kirstie Lew as a tattoo artist. Lewandowski had done a tattoo for Losek before. The new tattoo, a caricature version of Flynn, wasn’t in Lewandowski’s typical style, but Losek still wanted her to do it.
Lewandowski says she was up for the challenge.
“She believed I could make it happen,” Lewandowski says. “It does add that satisfaction that I got to do that for someone.”
The tattoo isn’t a traditional memorial tattoo with a dove, a heart or even Flynn’s real name. “Gayle” is written in script under the design of Flynn. Instead of a serious tribute, it was important to Losek to represent Flynn’s true personality: silly, a little weird and unwilling to take life too seriously.
“I needed something that was going to make me smile when I thought about it,” Losek says. “That was another reason why I went for the goofy [design], because it’s really hard to think about her and not think about the sadness of her being gone.”
A Sun-Times series on the stories behind body art.