What's He Really Thinking Before He Proposes?

Sure, maybe he looked confident when he got down on one knee, but this is what really was going on! Three guys dish on what went through their heads before they popped the question.

Digital Content Marketing Editor
Photography by: Courtesy of Lucinda Samperton

"I was having trouble seeing straight."

Kyle Huebbe/35/New York/Market Manager for Brooklyn Flea + Smorgasburg


Not all engagements have to be a total surprise. Case in point: Kyle's fiancée knew he was going to propose, but she didn't know when. "We actually picked out the ring together—my fiancée isn't a huge fan of surprises and I didn't want to make a mistake! I agonized for months about it, and finally just asked her to come help pick out a ring. We walked into Catbird in Williamsburg, Brooklyn and the first ring we saw we pretty much knew right away it was the one," he says.


The proposal finally came when they were both on vacation in Vieques, Puerto Rico talking about marriage and commitment. He got down on one knee—both of them in their bathing suits—and asked her to marry him. "I was so nervous and it felt like such a huge deal and I was having trouble seeing straight. She knew I was going to propose, but you never know for sure it's a yes! Until it is."

"The month prior I was thinking: 'Good god, how am I going to pull this off!'"

James Viscardi/28/Tennessee/Editor-in-Chief Comicbook.com  


James didn't meet Mallory until their senior year of college, and only started speaking to each other after a mutual friend introduced them at a Cinco de Mayo party. But it wasn't until they ran into each other at the university's photo studio when they began to connect. "I ended up proposing to her in the exact same dark room where we first starting talking. After I got the plan in place, all I could think the month prior was, 'Good god, how am I going to pull this off!'" he said.


The day finally arrived, and he decided he would ask Mallory to put one of his photos into the processing solution in that darkroom—and the photo would be of a ring. Mallory had a work emergency that morning and ended up meeting James at the studio in complete frustration. "So, she meets me there—and comes in like a bat out of hell! She put the photo into the solution and thought it was her BlackBerry!" 


Finally Mallory shook the photo clear and uttered "Oh my god." James was kneeling behind her with the ring, he remembers: "I kept thinking, 'What if she says no?' ... 'What if I overestimated the closeness of this relationship?'" Luckily, she didn't say no!

"I didn't want to say anything stupid."

Dan Asaro/30/New York/Pro Audio Sales


After six years of dating—and all the hints dropped by Dan's now wife—he knew that it was now or never, saying, "I decided I would propose at a family get-together, which was on a dinner boat going to the Statue of Liberty. I kept the ring in my pocket the whole time, constantly checking to make sure it was still there." When they finally got to the statue, Dan gathered his family and made a speech. 


"My main fear was that I didn't know what I was going to say, as I was pretty terrible with expressing feelings, and didn't want to say anything stupid," he remembers. But before he could even finish asking, his now wife grabbed the ring and put it on her finger!


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