When Aly Jiwani began to consider taking the next step with his anagram-loving girlfriend, Paula Acuna, he had a vision for the perfect puzzle proposal.

“One of our earliest memories is using our Chicago Tribune app on her iPad and zooming into the Jumble page,” says Jiwani, 30. “Then we use a piece of scratch paper on the side to solve it.”

Jumble is a cartoon-word game combination in which you unscramble four words, and once you unscramble those words, there are circled letters within the words, and those letters are used to solve a mystery answer that is based on the cartoon, according to David Hoyt, the Jumble’s wordsmith.

Jiwani says Acuna, 27, loves word puzzles, everything from The New York Times crossword to a book of Sunday puzzles he gave her. “It’s a thing,” Jiwani says. “I enjoy doing the puzzles with her. She’s way sharper at puzzles than I am.”

Jiwani sought out the Tribune about six months ago to make his proposal plans come to life.

“I began doing research in terms of the differences between the Chicago Tribune (newspaper) and the … Tribune Content Agency (the separate business unit that syndicates articles and features),” he says. “I had a friend at the Tribune, and she connected me to the agency. It took me two or three e-mails, but after following up, I was put in touch with David directly.”

Romantic puzzle proposal worked perfectly

The puzzle that Acuna completed.

Jiwani, who was introduced to the Jumble by Acuna, says he “was pretty starstruck” when Hoyt reached out in January via e-mail and then a phone call. “Once he and I got on the phone,” says Hoyt, “I told him what his options were.”

Collectively, Jiwani and Hoyt started coming up with ideas on what the answer to the clue would be. After an initial failed pitch that “wasn’t punny enough”, Jiwani came up with the answer: “Has a nice ring to it.”

Once that was decided, Jiwani was tasked with coming up with a setting for the cartoon.

“I started thinking about something that’s personal to us,” says Jiwani. “We like to sail on Lake Michigan, so I pitched that to Jeff (Knurek), the one who does the drawings. I came up with us being on a sailboat, with our dog Benji as well, with me going down on one knee with the ring in hand.”

Knurek, the Jumble cartoonist, did his best to include all of Jiwani’s ideas in the image. “I did my best to bring them into the Jumble world but still maintain their features, so people can look at the cartoon and say, ‘Oh yeah, that’s them,’” says Knurek.

The last element was the dialogue in the cartoon, which Hoyt says was crucial.

“We had to make sure that the dialogue all made sense,” he says. “In this case, because it has to do with what’s being said, it was important that the dialogue all match. It has to play for everybody and be completely understandable. And that’s the trick.”

Jiwani came up with the wording for the dialogue, which read: “Would you like to be my first mate for life?”

“The first mate is a boating term,” he explains, “which is used for the person second in command. Paula will immediately get it. It’ll be nice and personal for us.” At the last minute, Jiwani says, the Jumble creators threw in a bonus: “David told me they added “Paula” to the dialogue! It’s truly personal now.”

Romantic puzzle proposal worked perfectly

Close-up of the cartoon.

Hoyt and Knurek say they’ve been approached many times to do birthday, proposal and anniversary Jumbles, but that there was something special about Jiwani’s story. “It’s a great story,” says Hoyt, “and a part of what makes it so great is Aly’s efforts. He’s a little sweetheart, and it was very delightful to work with him.”

Jiwani says he is “really grateful to the Tribune staff, David and Jeff especially” because they were “genuinely excited” with him. “They didn’t look at it as a chore or a special request,” he says. “They’re super into it.”

Acuna’s parents, who are retired and living in Phoenix, Arizona, were also ecstatic about Jiwani’s plan for a Jumble proposal – so much so that her father subscribed to the Chicago Tribune print newspaper for one year so that he could see the Jumble when it was in the paper on April 8.

“As I talked to my future in-laws about what I was planning, her father drove around Phoenix looking for a newsstand that sells the Chicago Tribune,” says Jiwani. “He calls me back and says he couldn’t find anyone that could guarantee the Tribune on April 8th, so he said, ‘I just signed up for a one-year subscription’.”

The personalised Jumble ran in approximately 600 papers. Jiwani says Hoyt and Knurek typically run the puzzles with the longer clues in the Sunday papers. With all the excitement and even after all of Hoyt and Knuerk’s efforts, Jiwani says the Jumble duo just “kept making it better” for him.

“The icing on top? David said, ‘It’s a Sunday night. Why don’t we all meet for dinner after?’” recalls Jiwani. He made reservations for the night of the proposal and told Acuna they were going to meet somebody special.

“I had no idea who I was meeting at dinner,” says Acuna. “David was the first one who greeted me, and then I put it together. He greeted me with a big hug.” Acuna was surprised by the whole proposal, too, and says it was a “very happy day”.

“It worked out well that I was focused on the words of the puzzle, and I didn’t look at the comic until I had all the words,” she says. “I looked at the puzzle and saw my name and that it was a proposal. I was trembling as I was writing in the answer.”

At dinner Acuna got to hear all the details about how the Jumble proposal came together. “It was a huge production, and everything he went through to get it done, like adding my name in there, makes it so special. Now he’s getting all the points for most creative. It was perfect.” – Tribune News Service

Editor’s note: The original headline for this post incorrectly called the word game a ‘crossword’ puzzle.