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Google Won’t Pop The Question For You

Proposing to your boyfriend


I’ve taken a lot of risks in my life. I gave up my dream job for a chance to move to Japan. I’ve eaten unidentifiable food on the dusty red highways of Cambodia. I’ve careened down mountains in Costa Rica going 110 kilometers per hour on a rickety old bus. These have all had varying levels of success, but I think the biggest source of pride associated with taking a risk was proposing to my now husband.

I’ll admit it—like many of the readers of A Practical Wedding, I’d never had a dream proposal in my head. No hot air balloons or a restaurant string quartet or a “romantic moment” in some “romantic place.” I never really even thought I would get married, so I was somewhat surprised to find myself starting to have “those” thoughts.

The day I made my mind to propose to my boyfriend was a beautiful one. It was 2008 and we were in Bangkok, one of my favorite cities in the world, and we had just finished an amazing dinner near the end of an extended trip through Asia together. It’s always been my opinion that it’s not really living together, sleeping together, or anything but traveling together that will let you get to know the inner personality of your mate better or faster. And this trip happily exposed a wonderful man to me, someone I knew I wanted to be with for a long time.

After getting home, I carefully worked on a small set of blank wooden matryoshka dolls purchased on Etsy, handpainting them with a theme from our trip, and a secret message. I finished them quite quickly, surprising for someone who is not really that crafty. But then I waited. And waited.

I spent hours Googling “asking man to marry you” or “proposing to boyfriend” then meticulously deleting my search history. The great Oracle that is Google held little. In fact, most of the suggestions were to do things to get him to ask you, not to grow a pair and ask. There were a lot of recipes for engagement chicken. Some even suggested you had to wait for Leap Day on February 29th or Sadie Hawkins–every four years–to ask, like it was some sort of novelty and that you needed an excuse or permission to ask.

Hell to the no, that wasn’t going to happen. Mostly because the leap year had just passed and it meant waiting another four years. That didn’t really jive with my long term plans.

So, what was I scared of? Emasculating him. Jumping the gun—isn’t it the man that is supposed to ask, so that the woman knows it’s for real and he’s “ready?” (Whatever that means!) I also worried about if he said yes for the wrong reasons, or that I’d come off being too assertive. Pretty much everything touched on in Carrie’s APW post about women proposing to men.

In the end, struggling with my thoughts (and Google) did nothing. I did not even have time to don a scarlet petticoat as the Leap Day tradition calls for, to “warn” him. He found the gift in its secret hiding spot, and my hand was forced. I dug up the tiny toy ring I had purchased, and since I couldn’t look at him, let alone find the words, I had him read the bottom of the dolls. “Will…you…marry…me?”

“Yes.” he stated. Clearly, strongly, unhesitatingly, and reassuringly.

A few days later I relayed the news to my parents who were living in Thailand at the time. The Skype connection was a bit slow and choppy, but there was no denying the look on my mother’s face. Nor any masking of the tears that started to flow. They were not ones of happiness.

Instead of, “I always knew it would happen this way,” she said, “But that isn’t the way it should be,” when I proudly declared I had proposed. I was so angered and confused in that moment. Didn’t she raise me to be a strong, confident, independent woman? Would she rather I wait to be “picked”? She rushed away from her end of the computer and my dad said, “That’s great news, kiddo. Let’s just give her a few days to get used to the idea.” Then we signed off.

The days following I experienced doubts myself. I was now embarrassed to tell people I had been the one to pop the question, fearing a reaction like my mother’s. Like it meant less, or like it wasn’t real because there was no diamond attached.

Much like Madeline’s story, people who first meet us always coyly ask in that voice (you know that voice), “Sooooo…how did he pop the question…” and at first I felt nervous and sad and scared, but now I feel damned proud to say “Actually…” and tell the tale. The matryoshka dolls sit proudly on our mantle.

Now, four years, a wedding, a few apartments, jobs, and international moves later, I feel proud of what happened. It’s increasingly not as unusual or rare anymore, and I hope it continues to happen so it’s not a “trend” and just a fact of life that occurs. It’s still hard for my mom to accept what happened. But gradually she’s come around. After all, a wedding is more than a proposal. It’s a marriage.

So, if you found this article by Googling “proposing to boyfriend,” here’s my advice: make it happen, Captain. Yes, it’s scary, and nerve-wracking, and people may not understand, but then again, it’s not their marriage, is it?

Photo of the matryoshka dolls from Kelly’s personal collection

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