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Picture this! A proposal through Pictionary

  • A game night for one woman gets really interesting
  • This man’s creative proposal incorporated a popular game
Pictionary proposal
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For one San Francisco man, a classic picture-drawing, guessing game was the perfect disguise for his March 8 proposal to his girlfriend.

“I was trying to think of a creative way to propose, and I wanted something memorable. I actually don’t know how I thought of it,” said Michael, who asked his last name be withheld.

After looking up proposals on YouTube and Reddit, the product manager decided he’d rig a game of Pictionary and have his would-be bride, Conny, guess her fate.

Michael and Conny have known each other for three years. Though they remember they met dancing, neither can remember the exact details of how they got together.

“We both remembered there was a strong chemistry,” Michael said.

After a year-and-a-half of dating, that chemistry warranted a proposal.

“I started thinking of it in November or December, and I started working on it in January,” Michael said of his Pictionary plan.

He began by searching for a Pictionary card with the word “marry” on it.  Then, he added the world “me” to the end of it.  Next, he plotted a belated birthday game night with friends where he would surprise Conny.

“I liked the idea of doing it at home,” he said. “I liked the idea of doing it in front of our friends, too.”

Planning the perfect Pictionary game became a bit stressful and two days before the game, he enlisted his friend’s help.

“I told my friend about it. I knew I needed some help. I needed an accomplice. He is the only other person that knew,” Michael said.

He needed someone else to ensure Conny would pick the right card at the right time. With the game rigged, the group of eight to 10 began playing. Halfway through the game, Conny started drawing and the group began guessing.

Some may have begun to guess what was about to happen.

“I did notice that the room went silent,” Michael said, adding that he wished he had paid more attention to his surroundings.

Shouting out fake guesses like “propose” and “ring,” Michael finally screamed “marry me!” Conny was excited she’d won the point. She was so enthusiastic, she didn’t realize Michael had just proposed to her.

“She was shell-shocked. I don’t even think she knew what was going on. I think it took her a few seconds to register it was a real ring,” he said.

When Conny realized the guess was real and not part of the game, she forgot to answer.

“She still hadn’t said ‘yes’ yet,” Michael recalled. “You still haven’t answered my question. Is that a yes?”

It was indeed a “yes.”

Conny wasn’t the only one surprised. The others at game night were, too.

“One friend told me he thought it was a cruel joke,” Michael said. “I guess it’s so out of the blue and just so unexpected.”

Michael said the attention his proposal has gotten online was unforeseen. He’d only hoped to plan something personal and special for the woman he loved. He didn’t expect it to touch people the way it has.

“I think it’s really cool,” he says.

For others considering popping the question, Michael has some advice -- the proposal doesn’t have to be expensive, and it doesn’t have to be complicated. It just has to be personal.

One other major point he stressed is making sure your partner is ready.

“I made myself watch a lot of old marriage proposals on YouTube just to scare myself off. I wanted to make sure she was ready,” said Michael, who’d discussed marriage with Conny beforehand.

Michael and Conny have yet to set a wedding date, but hope to get married later this year. 

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