What Happened When I Tried To Woo My Man

A man and a woman on a hike.
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As my boyfriend likes to remind me, he's a catch. And at the risk of sounding obnoxiously in love, he's right. He cooks me dinner every night and usually does the grocery shopping. Every time I finish taking a shower, he rushes into the bathroom to hand me the towel from the door, just so I don't have to drip on the floor. He once fished a Softcup that was stuck in me out like it was nothing ... and then proceeded to give me three orgasms.

Which is why when I found myself in a fight with him that started with my rejecting the perfectly good salad he'd made and ended with me screaming, "We're not even doing anything for Valentine's Day or our anniversary!" I knew I was being a brat.

"Why do I have to plan something? Why don't you plan something?" he said, exasperated.

"I already have! It was supposed to be a surprise, but now that's ruined!" I screamed.

I'd hatched the plan a few weeks before, knowing I might get all crazy around Valentine's Day and our anniversary (which is the weekend after, creating a perfect storm of expectations). I like to fancy myself the type of woman who doesn't care about those holidays — and in so doing often end up resenting it when the guy fails to read between the lines and sweep me off my feet anyway. I am aware that this is the worst.

I was tired of the double standard I was holding that the man take charge of the romantic planning, and I wanted to do something special to commemorate our year together. So I decided I would flip the script and sweep Jacob* off his feet for our anniversary instead. I'd get the special day I wanted, and he would get to feel like the one who was being totally taken care of for a change.

The Plan

As you can see from that fine RBF above, this was not going to be an easy man to woo.

I planned a packed day: in the morning, flowers, his favorite bagels, and a trip to a gallery that was almost our second date; in the afternoon, checking in to The Gansevoort Hotel, where he'd be wooed with the full romantic package; in the evening, a fancy dinner at the first restaurant we went out to as a couple, followed by dancing. I would treat him to everything, and give him a different heartfelt card for each part of the day — four romantic notes in total. All day long, I would flip the conventional script and be as romantic and chivalrous as possible towards him.

Part 1: Bagels & Surprises

I woke up at 5:30 a.m., which was definitely not part of the plan. I felt giddy and excited in that way you sometimes feel on your birthday. By the time he woke up at 8:30, I'd been awake for hours, staring at him sleeping like a creeper.

"Happy anniversary," I cooed.

"Happy one year since we f*cked," he replied, giving me a kiss. He went to yoga, and I went to pick up his favorite bagels, along with some flowers.

One year ago, the first time I went to his apartment, I brought flowers. He'd blushed, put them in a vase, and, as the weeks went on, they remained there. One year later, like me, they were still in his apartment. I decided I liked the romantic symbolism of adding some fresh leaves to the mix, and watching those go brown over the next year too. Maybe it would become our tradition, until we had dried flowers from every year, all mixed together. I was pleased with my romantic self.

"You got bagels!" he exclaimed when he walked in. "Are these new flowers or the same?" I explained the idea, and he nodded, as if impressed by my thinking, but not particularly wooed. After we finished breakfast he opened my card, smiled while reading it, and made not one but two sexual puns out of my cheesy phrasing. "Where are we going?" he asked for about the thousandth time that week.

"It's a surprise."

"I don't really like surprises. They just make me anxious."

Part 2: The Date That Never Was

Our first destination was the Neue Galerie. I'd picked the spot because the week we got together, he kept trying to make me go see an exhibit there, the Egon Schiele self-portraits, and we kept not making it because we basically couldn't get out of bed. I thought my remembering the gallery one year later would touch him. But when we arrived, there was a line around the block just to get in because of a new Munch exhibit. F*ck.

"This is where we're going?" (Was I imagining it, or was that disappointment in his voice?) "It's gonna be awhile."

"Yeah, this is it. Do you get it? It's where you wanted to go to see the line drawings when we got together."

"But the Schiele isn't here anymore. It was a mistake not to go. They were so good."

"Well, we were too busy falling in love!" I mumbled, starting to get annoyed. I suppressed the urge to pout that he didn't appreciate my gesture.

We decided to go to The Met instead, and he seemed to relax as we resumed our typical dynamic of him leading the way. He navigated the museum with ease and showed me some of his favorite rooms, putting his arm around my waist affectionately as he asked me to guess his favorite Vermeer painting. I did, easily. He smiled. "You're only the second person to guess that."

"How many people have you asked? Is this like your test for every woman?" He laughed, and pointed out a another painting. "You totally would have been into that dude."

At least he knows my type.

Part 3: "Get Suite & Romantic"

"Where are we going?" he asked again, even though I wouldn't tell him. I put the GPS on my phone, but at one point, I got confused because we were in the West Village and showed him the map, thinking he wouldn't be able to guess the exact location. "Oh, I know where we're going now! We're going to The Gansevoort ."

He was right, and I was relieved by how excited he sounded, how impressed and pleased. "I got drinks there once on the rooftop and it was really nice."

I felt like a baller while I led him up to the room, where I'd arranged for the full "Get Suite & Romantic Package." There were strawberries and champagne, two lush bathrobes, monogrammed pillowcases, and roses, all waiting for us. We made ourselves at home, exploring the room like two kids, checking out all the fancy soaps, the Illy espresso machine.

Jacob was impressed, and slipped on his robe. Like I said earlier at the museum when we were looking at 17th century portraits, he would have made a good aristocrat. I sprinkled some rose petals on the bed, because when in Romance.

Jacob was more interested in the huge mirror placed next to the bed, and swept the rose petals out of the way, climbing on top of me. He might have been the one getting wooed, but a Top is a Top, and, as I was beginning to realize, romancing someone doesn't mean you can't still end up getting ravaged.

Part 4: A Dinner Full Of Feels

It was time for dinner. At this point, I'd realized the surprise tactic wasn't really making him enjoy anything anymore — it just made him uneasy. While I love surprises, he likes knowing where he's going, and I was learning that part of being truly chivalrous is just respecting that, and to stop imposing my idea of romance on other people.

I told him we were going to the restaurant he took me to when we first started dating after I'd pretty much demanded "he show me somewhere cool and new." I thought there was a poetic justice in returning the gesture one year later. If I'd been asking him to "prove" anything to me in the beginning, it wasn't that he could take me to a fancy dinner so much as that he would show me new, interesting things. In the last year, we'd tried more new restaurants and had more adventures than I could count, and I wanted to thank him.

When we got to the restaurant, the ambiance was dim, quiet, and romantic. I'd looked ahead at the menu and decided it wouldn't be an issue on our now-vegan diets. But I hadn't called ahead. As it turned out, the dishes I thought could be modified couldn't be, and we ended up basically only eating brussels sprouts, beets, chickpeas, and almonds for dinner. And beets. And beets. Sh*t.

I apologized, and told him that the day had revealed a lot to me about the way I plan overzealously and somewhat carelessly. I had concocted so many parts to the day that I forgot to make sure about the basics at times, like directions or the menu. I'd written him four cards instead of one, and as a result I didn't feel that great about how I'd conveyed any of them. It was a good reminder that when it comes to experiences, it's about quality, not quantity.

"Well, the good thing about planning is that the more you do it, the better you get at it," he replied kindly. I smiled, reminded why he's been so good for me, how much he has led by that example, and in so doing, helped me grow. I felt the emotions bubbling up, and I wanted to say them, but for the first time that day, I was scared. I'd said it all in the cards, but not the way I wanted to, and this was the moment.

He noticed me gathering my nerves and he took my hands in his. We looked each other in the eyes and smiled. I told him exactly what this last year has meant to me, and why I am so grateful to be with him. I started to tear up, and so did he. He thanked me for the special day, said how even though I thought I hadn't done as well as I'd wanted he was touched by the thought and care I'd put into the day. For him, it wasn't about the result anyway. It was about sharing life with me, rooting deeper into each others' worlds, about loving me properly every day.

I left the final card in my bag. Everything I'd said in it, we'd just said better. Instead of dancing, he said he wanted to go home and cuddle — an unusual suggestion for him (he likes to go out) that proved to me he was feeling truly relaxed and intimate.

Part 5: Oh Sh*t

When we returned back to the hotel, Jacob told me his intestines were burning. I'm not sure if it was our meal of all those vegetables or an allergic reaction to being surprised all day, but he ended up on the pot for the next half hour. Because there was no fan in the bathroom, I heard everything. And you know what? I honestly didn't care. I played a game of Words With Friends on the phone with him so he'd have some virtual company.

"True romance is playing Words With Friends when your partner is pooping," I yelled to the bathroom.

"That was a good move," he shouted back. When he felt better, he held me to his chest and told me he loved me for what must have been the tenth time that day.

The Morning After

While I know that what Jacob says is true — that every day together is special, and that it's most important to show that through our ordinary actions, not just once a year — I also think that I was right to want to make our anniversary a special day.

In the end, the closest I felt to him was not when we were laying on rose petals, but when I was simply taking the time to look him in the eyes and tell him all the things I might otherwise assume he knows I feel about him. It was nice to have a day that was explicitly about bringing us both into that headspace. We took the time to appreciate where we've been, to feel grateful for where we are, and to get excited about where we're going. Sometimes I think you just need a break in routine to do that, and a staycation can be a great way to pull that off. He was totally relaxed by the end of our night away, and that alone was worth it.

I'm not sure if my planning extravagant anniversaries will be a tradition from now on, but I do know that it felt good to realize I could be genuinely just as gratified by wooing someone as I could feel being wooed. It didn't emasculate him in any way in my eyes to be on the receiving end of my chivalry, and if anything, it emphasized the reasons why our dynamic works: I'm a hopeless romantic with big, idealistic ideas, and he's the guy with a sense of direction who can help me execute them. Even when I was wooing him, we functioned as a team.

As girls, we were taught to more or less expect the fairytale to come to us. Everything had a clear happy ending, creating (in my case anyway) often unrealistic expectations when it came to romance. It was pretty gratifying to remember that I don't have to wait to be rescued or kissed, wined or dined — I can make it happen anytime I'd damn well like. My fairy godmother is my credit card, and though I've found a true prince, I don't have to act like a princess waiting to be kissed. In fact, sometimes I can be the author of the fairytale altogether.

Some names/images in this story have been amended to protect the privacy of those mentioned.