How to Guarantee Your Proposal Won’t be Featured on HowHeAsked.com

To say that my wait for Remus’ proposal became a bit torturous is an understatement. We openly discussed when we wanted to get married, and once agreeing on a timeframe, wound up looking at venues, finding one we both loved, and putting a deposit down on said venue, thus securing our wedding date. And all before he actually proposed.

I was eager to let our nearest and dearest know when to mark their calendars, but Remus insisted we wait until he “officially” popped the question. I argued that putting a deposit on a venue is pretty official, but his definition of “official” included a ring on my hand, because “if you tell people we’re engaged and you have no ring to show them, they’re going to think I’m some kind of moron who can’t get his shit together.”

So fine, I’ll wait until you get a ring to let people know we’re getting married. How long could that take? A couple of weeks? Maybe a month? Fine, whatever. We booked our venue almost a year and a half in advance, so there was plenty of time.

But Remus’ job had other plans. For the next five months any lunch hour he planned to spend perusing Chicago’s jeweler’s row was overtaken by fire-drill emergencies, unreasonable last-minute client demands, and project plans that were so mismanaged that it’s a wonder they ever got done. Hoping to get to the jewelry store before it closes at 7:00? Sit your ass down, we need to pull another all-nighter. My wait for the proposal dragged on and on as his work life became more and more tyrannical, and the doubtful “does he even really want to get engaged?” seed started to take root in my mind.

He has since left that job for one that actually champions a work/life balance for its employees, and I’m not sure which once of us is happier about that. As our “year and a half to go” timeline crept closer to “one year to go,” I started to get extremely anxious about when we could finally spill the beans. He eventually shared that “it’s out of my hands at this point,” leading me to (correctly) assume that a ring had finally managed to be ordered.

Then came the weekend that I was convinced it was coming, because homeboy could not have been throwing up any more signals.

I had made Saturday night dinner reservations at one of our favorite restaurants to celebrate his first week at his new job. That Friday night--while at a wedding DJ showcase, of all places--he mentioned that he needed a decent headshot taken for his profile at work, so he might dress up a bit for dinner so I could take some photos of him that night, too.

“What are you going to wear tomorrow night?”

“I don’t know…jeans and a not too terrible top, I guess?”

“You should wear a dress. You look so good in dresses.”

Hm…OK…

At some point in the evening I commented on how shitty my unpainted nails looked.

“You should treat yourself to a manicure before dinner tomorrow night.”

Sure…maybe I’ll do that… (and I did).

The following night Remus dressed up in a button down and sports jacket, and I put on a dress that went with my freshly manicured nails. Before leaving for dinner he suggested we head up to the rooftop deck on our building to take those headshots. On our way up he commented: “I hope there’s no one else up there…”

OK, Casanova, I’m picking up what you’re putting down…

I now had no doubt in my mind that the proposal was about to happen.

So we went on the (vacant) rooftop with views of the Chicago skyline just as sunset was starting on an unseasonably warm and sunny November evening, and I took a series of headshots of him. And then…we left for dinner.

Why the hell didn’t he do it on the rooftop?! Is he doing it at the restaurant? I was pretty clear that my #1 rule for this whole thing was “no public proposal”…

We had a fantastic meal, complete with drinks and dessert (holla, Siena Tavern), and then…he suggested we go grab another drink somewhere else. He suggests Sable. Which is the somewhat swanky bar/restaurant where we met for the very first time.

Oh…he’s going to do it at Sable! I guess that’s appropriate, and I can get past the “no public proposal” stipulation as long as he doesn’t make a big show of it.

We get a cozy table for two at Sable and enjoy a couple of cocktails. And then…we head back home.

What the fuuuuuuuuck?

“Let’s stop by the park near our building before going home.”

OK, so we’re doing this in the park? Yes, we must be doing this in park. We’re on a bench overlooking the river, there’s no one else here, the sun has set and the city is all lit up and glowing, any second now he’s going to pull that thing out of his pocket and officially ask me to marry him!

And then…we went home, changed into our pajamas, and settled in for the rest of the night. And my brain kind of exploded.

What the fuckety fuck fuck fucking fuck??? He was totally going to do it tonight! Right? Wasn’t he? What was all that “wear a dress,” “get a manicure,” “rooftop,” “bar where we met,” “romantic bench time in the park” bullshit about??? Did he chicken out? Does he really not want to do this? Am I one of those psycho-bitch girlfriends who pushes to get married when her boyfriend has no interest? But we openly talk about it all. the. time. Is he just messing with me? Was he purposely trying to throw me off all night long so that I’ll be truly surprised when he actually does propose? That’s so cruel! What a fucking asshole! What in the ever-loving fuck is going on??!!

My inability to maintain a poker face around Remus was exacerbated that night and he could tell that something was bothering me. When he made the mistake of asking about it, I burst into tears.

“What are you doing? Are you fucking with me? Could you have misled me any more all night long?”

I didn’t even need to mention the word “propose” for him to know what I was talking about. He insisted that he wasn’t fucking with me and simply thought we were just having a nice romantic night out. I declared I was going to bed and was in such a depressed funk all day Sunday that we barely spoke.

Coming home after work on Monday I was still feeling miserable, and as luck would have it, we had a Skype call scheduled with a wedding photographer. I was still wondering if he was having second thoughts about getting married and wasn’t even sure it was worth having this call, but that was a conversation I couldn’t even stomach having at that moment, so we carried on with the meeting.

At the end of the call the photographer promised to email us both a link to one of her full wedding galleries for us to look at, and then we signed off, I changed into my pajamas, and asked if he wanted to watch something off the DVR.

“Sure, but do you want to come into the office first and look at this gallery the photographer sent?”

I look at my phone to find no new emails waiting for me.

“Did she already send it? I don’t have any emails.”

“Maybe she just sent it to me. Come take a look.” And he heads into the office. And now I’m pissed off at the photographer (along with the world at large).

Stupid fucking photographer, can’t even manage to include me on an email when I’ve been her primary contact in setting this all up. Who doesn’t include the bride on their emails? Like the groom is of any use on his own in the wedding planning process. If you can even consider us a bride and groom since I’m not even sure he wants any of this anymore…

I grab a handful of Mike & Ike candies from the box on the coffee table, shove them into my mouth, and head toward the office, still grumbling about this dummy photographer.

And then…I walk in on Remus down on one knee in our office with a ring box in hand. The exact words that were exchanged are private--though at one point I did cry out, “I have a mouthful of Mike & Ike!”--but he officially asked me to marry him and I officially said yes. And he explained that he didn’t even pick up the ring until that day, so he never had intended to propose over the weekend, but knowing it was coming soon he apparently got a little overzealous about what was to come and misrepresented a multitude of prime proposal moments.

And that is how to guarantee your proposal won’t be featured on HowHeAsked.com: have it done while you’re in your pajamas with a mouthful of candy after have a mini-mental breakdown.