My Girlfriend Definitely Thinks I’m Proposing Next Week And I’m Definitely Not

My Girlfriend Definitely Thinks I'm Proposing Next Week And I'm Definitely Not

It was something I heard months ago. “She’s had a standing appointment every Friday,” I was told. “You know, just in case she gets proposed to this weekend.”

I was confused.

“Like, if she gets proposed to and her nails look like shit, that would be a total disaster.” And that’s when it clicked. I had no idea what type of calculations and planning actually went into proposals. Whereas I thought most proposals came as a surprise to an unsuspecting party, I quickly learned that this was nowhere near the case.

If the anecdote my girlfriend relayed to me was any indication, it was completely and utterly evident that any warm-blooded male after the age of 25 who still ticks the ‘single’ box on their W2 isn’t only treading in the engagement water – they’re gasping for air while sharks circle them as they bleed out.

Booking a hotel room months in advance is a savvy move. Not because you get a cheaper rate or because you can guarantee vacancy, but because by the time you actually throw your suitcase on the ground and toss on the plush robe, it’s like you never even paid for it. The credit card transaction is so many statements ago that it’s simply a sunk cost.

Her first tell that my bag wasn’t going to be a half-ounce heavier should’ve been that I got a “queen suite.” In terms of hotel rooms, this is essentially one step up from “the room that faces the parking lot.” This wasn’t a honeymoon suite, nor was it even a king suite with a lake view. This was your standard, run-of-the-mill hotel room.

But it also has the words “queen” and “suite” in the title. Concerning.

I’m not one for grand romantic gestures. I let Meg Ryan’s counterparts handle those. If I’m atop The Empire State Building, I’m imagining Sam Baldwin, Annie Reed, Mindy Lahiri, and Danny Castellano – not trying to emulate them. When I’m at a scenic outlook, I’m questioning the integrity of said lookout’s boardwalk – not positioning a professional photographer in a random pine tree telling them to start shooting the moment I fake yawn. I’m a reasonable man with reasonable expectations. So when I proposed a trip to a romantic island where horse carriages replaced cars and blazers were standard dress after 5 o’clock, my brain was filled with rieslings rather than rings.

Getting drunk on an island is the ultimate for some, but for others (read: your girlfriend), getting something else on an island is much, much more desirable.

It wasn’t until about two months after booking our trip that someone approached me in a hush manner. My girlfriend and his wife were within an earshot of us. When he began to whisper, I thought it was going to be about something less, well, intrusive – like cutting away to watch the game, a good-looking girl who I hadn’t seen enter the restaurant, something being in my teeth. He, however, was coming to me with grave concerns. Not concerns about what could possibly happen, but concerns of whether or not I knew what was going on behind the scenes.

“So, uh,” he hesitated, “I heard some rumblings about your trip.”

I smiled obliviously. “Yeah, man, I’m pretty excited,” I relayed before realizing he was still holding eye contact.

“Are you proposing?”

My stomach didn’t drop, but my drink nearly did.

“Uh, what?”

“Like I said, I’ve heard some rumblings.”

I don’t remember how I reacted, but I know that my reaction wouldn’t have been ideal in the eyes of some. Namely the person sharing the queen suite with me in just a few short weeks. What he said wasn’t an unreasonable assumption. It was a conclusion he came to, I imagine, through conversations had behind closed doors with the person who shares his queen suite. A person close to the situation; a person who’s gone through this before. Most importantly, a person who clearly had a much better outlook on the situation than I had.

When you’re lost in a familiar geographical area, there’s a moment of panic where you realize that you have no idea where you are. South could be north, north could be south, but you keep plowing ahead hoping to have that “aha!” moment where you finally realize that you’ve seen your exact surroundings a million times over. This moment, for me, was when everything clicked.

“She definitely thinks I’m proposing then, doesn’t she?”

That question wasn’t rhetorical, but his complete and utter lack of response pretty much said, “Of course she thinks that, you fucking dipshit.”

The hotel. The island. The timing. It all added up to one singular thing that totaled up to way more than I had originally budgeted for the trip.


I began putting the pieces together in the coming weeks. With a watchful eye, I started tracking her every movement.

“It would be pointless for her to get Friday manicures,” I told myself. “She’s invested in that one fateful night.”

The puzzle I was trying to solve became even more difficult, as if the dog had eaten a piece or someone forced me to solve it upside down. I wondered how I could possibly figure out if she actually thought that this was happening without actually asking her if that was the case.

My mind raced about my decision-making abilities. “Wait,” I wondered, “If everyone thinks I’m proposing, does that mean I should actually be proposing?” I began feeling like the slow kid in class who couldn’t comprehend long division while the rest of the class endlessly scribbled in their notebooks. Maybe I was the crazy one.

After some thinking (also known as “staring into the bottom of a glass”), I realized that I had a good head on my shoulders. That life-altering decisions and grand gestures of this kind were up to me, not others. And that I’d receive a barrage of overdraft emails if I even Wazed the nearest jeweler.

Before dinner one night, I went out on a limb. It was probably the cabernet speaking, but the question that came spilling out of my mouth likely shocked her.

“So you know I’m not proposing on Mackinac Island, right?”

This question was brash for several reasons. If she did, in fact, think I was proposing that night, she played her cards closely. The answer could have possibly been tears, deflation, sadness, or all of the above. But without skipping a beat, she looked at me and stated, “Oh, I hadn’t thought about that.”



Crisis averted.

Until a few days later when I received a text that was read in the same vein as an “I’m late” text from your high school girlfriend.

“What are you doing after work on Wednesday?” she asked. “Want to get mani-pedis?”

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Will deFries (Twitter / Instagram) is a Senior Writer at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram). Email me at

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