The Pitfalls Of Planning A Proposal

The Pitfalls Of Planning A Proposal

I very recently got engaged to my girlfriend. To some of you, that’s exciting, and to plenty of others, that sounds like a death sentence. I empathize with both opinions. Now that the proposal is over and was successful, I can say that the planning process for the event of proposing is, in and of itself, insane. There were a lot of things that I realized as I did crazy things like harass the tenants of the place where I wanted to perform the proposal and check the price of bulk rose petals. Most of what I realized was that this whole idea was archaic and nuts, but we all know that love makes us do crazy things. So, there’s that.

Here are a few other things I realized in the process of planning a proposal.

First of all, there was the ring. Just choosing it from the mountain of options that are available was hard. I knew what style she wanted (the phrase “fuck a halo” was tossed around) but even so, there are about a million different variations to pick from. I had to decide where I wanted to purchase the ring from, and there a bunch of factors to consider there, too. One place ended up having a bitchin’ warranty deal where they cover the ring and all the stones for life, so I went in that direction because other options were insuring it like a car and paying for the rock was expensive enough. I won’t go into the various awkward moments that occurred in being a woman looking for an engagement ring for another woman. I think there were several store employees who thought I was just a very self-centered millennial looking to blow a few G’s on a ring to “celebrate me.” Sorry to whoever put down money in that pool.

As it turned out, it took me multiple visits to different places, and then a little over three hours at the chosen location to pick the final version of the ring I wanted. An employee who terrified me to my soul with stories about how much he hates his in-laws was admittedly very helpful in teaching me about diamonds. Who knew those expensive suckers were so complicated? Then, he comforted me as I sobbed and emptied my bank account for a three-stone vintage beauty of a ring that I wouldn’t even get to wear. It was a mixture of emotions.

The ironic thing about planning a proposal is that if you’re preparing to do something that involves even some level of planning ahead, at some point your significant other will probably think you’re breaking up with them. I took a lot of weird phone calls and snatched my vibrating phone away from her hand way more often than usual in the days leading up to the proposal. I was even, at times, snappier and more irritable than normal because I was dealing with things like finding a ladder tall enough to get me on the roof of a house and trying to hold her hand in a way that allowed me to double check her ring size (not a very effective mode of measurement, in case anyone was wondering.) In an effort to avoid her questions about any of these things, I distanced myself from her and basically led a double life for a month or so, and that was hard. It’s very strange when the one person that you normally share everything with is totally in the dark about something like that. It feels like you’re doing something shady and wrong even though all you’re trying to do is literally plan to ask them to spend their life with you.

Finally, it wasn’t until I had handed my girlfriend her flute of champagne in the very moment that I realized I hadn’t planned anything specific that I wanted to say in the proposal speech. Something should come before “will you marry me,” right? Was I supposed to list all the reasons that I loved her at this point? Yes, of course I was, but because I’m an idiot and was so caught up in the rest of the details that I’d given minimal thought to what I’d actually say in the moment. Thankfully for me, I think well on my feet, and although I don’t remember a thing I said, she assures me that it was a lovely pronouncement of love. At the very least, she didn’t slap me across the face and/or say no, so I must have done something right. The fact that she said “yes” was all I could really ask for. Now I just have to plan a wedding, so if anyone out there has any extra cash they’re looking to get rid of, or a venue that can hold at least a couple hundred drunk rednecks, hit a sister up.

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Rory Gilmore

Rory Gilmore on the outside. Emily Gilmore on the inside. Email me funny shit at

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