The Best-Laid Wedding Plans

Jennifer Keishin Armstrong
17 min readSep 8, 2019

Originally published in the anthology Altared:

I stood on a pedestal, thick white satin hugging every curve of my butt without scrunching, falling precisely to the tops of my silver-sandaled feet without bunching. The top seam of my strapless gown skimmed the top of my breasts, and my bare skin peeked seductively through the lace-up back to my exact specifications. I don’t mind saying it, because I’d picked this dress myself and had the seamstress rework it ’til it was basically couture, and because I’d endured five fittings to get here: I was a vision of perfection.

The gal on the pedestal next to mine, drowning in pouf and lace, caught my eye in the mirror and sparkled like we shared a delicious secret. “What’s your date?” she asked, all aglow. My first reaction: Should she really be asking me about dating? I’m engaged, after all.

And then I caught my reflection in the mirror again, remembered why I was here. Panic set in. Let’s see, it was late July. What would make sense? Not August. That was too soon. “September.”

“Ohmygod, me too! When?”

“Uh, the second weekend.” Total gaffe: Any bride has memorized not only her own date, but the exact date of every Saturday within at least four weeks of hers.

“Oh, mine’s the 18th, so a week later.”

An embarrassed flush spread from the top of my dress, up my neck, to my cheeks. I’d put my wedding on Sept. 11. Not impossible, but … unlikely, a mere three years after the terrorist attacks. The shop fell silent then, save for the occasional tussling of tulle. Who knows if she was onto me, but that was beside the point. When I stood there lying to a total stranger, it seemed all too obvious, the symbolism cinching my lungs like the seamstress yanking the strings of that lace-up back: I wasn’t being honest with myself or my fiancé. We’d had a date, nearly a year before, and we’d been postponing ever since. Actually, I’d been postponing. And I wasn’t sure I’d ever stop.

The truth about my feelings showed up in the wedding planning first — whether I was barreling forward with the goal-orientation of an Olympic athlete, oblivious to anything except getting to the finish line; dreaming of a destination wedding that would take us far away from our everyday reality; or convincing myself that a cool New York wedding would make us into the happy urban couple I wanted us to be. But the fact is that I got so caught up in the planning itself that I couldn’t see that every one of those phases was telling me something very important about my relationship.

Facing my indecision proved the biggest struggle of my life. When doubts first began whispering through my head, they didn’t make sense to me. I’d spent so long loving my fiancé — more than a decade, since we met in college. I had found a man who shared my love of Shakespeare and Elton John, who was taller than I but not too tall for me to kiss, who was smart (a nonnegotiable requirement) and funny in the exact right way (puns and sarcasm are both essential). He balanced my remedial financial skills with budgetary obsession and was so organized he made me feel wonderfully free-spirited (though anyone can see from my meticulous day planner that I am not). I was so sure we belonged together that I followed him from Northwestern University in my hometown of Chicago to Southern California (where he was stationed as a Navy officer), back to Chicago (so he could go to grad school at Northwestern), and finally to a New Jersey suburb of New York — where he got a job at Mercedes-Benz, and I could finally chase my national-magazine dreams after years of local newspaper reporting. And I did just that, landing a gig at Entertainment Weekly — which required I start as an assistant, but my diligent spirit was prepared to do what it took. We bought a condo in Jersey. Dan proposed. Everything seemed on track.

So how could I feel like it didn’t quite fit? I had methodically plotted a perfect wedding that I didn’t want, the same way I’d carefully constructed a perfect life I was beginning to realize I didn’t want. The evidence was there in the preliminary wedding preparations when a strangely errant desire immediately surfaced: It seemed I wanted a small, casual affair, with just our closest friends and family — not the princess-bride wedding I’d always imagined having. Instead, I envisioned an evening party, essentially, kicked off with some vows followed by a yummy dinner and maybe a little dancing.

Then I even found the dress. My mom and I were walking through a mall in suburban Chicago when I was home for Christmas. This gorgeous little thing shimmered at me from a shop window: silvery white, with a halter top, plunging back, and swishy skirt that fell just below the knee. Sort-of a Marilyn Monroe number, with less plunge in front and more dip in back (perfect, since my curves are a more modest than Marilyn’s and my back is one of my better features).

I stopped in the middle of the mall when I saw it, and I gasped enough that my mom reacted as if I were suffering a grave illness. “I’m fine, Mom,” I assured her. “It’s just … that’s the dress.”

“It’s pretty. Are you guys doing something for New Year’s?”

“No, that’s my wedding dress.”

I never expected what came next. Not from my mom. My mom is cool, laid-back, and, more than anything, all about letting her kids make their own decisions (e.g., mistakes). The woman let me move to Southern California right after college into an apartment that I’d never seen, with a job at a far-flung newspaper that was paying me $320 a week, and never issued one word of doubt or warning. But weddings, I learned, do funny things to people beyond the bride. “You would wear that to your wedding?” she said. “How would you wear a veil with that?”

“Um, I’m not wearing a veil.”
“You have to wear a veil. You need a wedding gown and a veil.”

She looked so indignant, was so emphatic, that, at the time, I thought maybe I did need a gown and a veil. The only person I liked to please more than my boss or my fiance was my mom, after all.

I never saw that dress again. But later that week, on a proper search for a proper dress in proper bridal stores, I found the one I’d tailor to perfection: a strapless, pure white column dress with a reasonable little train and silvery beading along the top. I got a veil trimmed with a little sparkle to match the beading. The silver bits reminded me of the shiny Marilyn dress I’d passed by — my (tiny, imperceptable) nod to the bride I’d wanted to be.

I’d fancied myself a modern woman who knew what she wanted and wasn’t afraid to get it. But I was slowly starting to see that the only thing I wasn’t afraid to get was a wedding dress that everyone else would think was gorgeous and, thank god, appropriate. And as for what I wanted, that was nothing more than a sparkle along my bustline. The wedding planning consumed me. So much, in fact, that when I look back at that time, even Dan hardly enters my memories. I was on autopilot, preparing for something I had been waiting for all my life. Whether I wanted it wasn’t up for discussion.

In my mind, I was doing it for him. For us. I had dreamed of this day for so long, but I refuse to use the excuse that I was brainwashed to, like all other girls, since childhood. I wasn’t dumb — I had the wherewithal to figure out I didn’t need a wedding to be a modern successful girl. But I was a searing romantic. Always had been, for as long as I’d liked boys. And it was because I liked boys so damn much. I’d always believed in true love, because I was always in love, period. This one had simply outlasted the others and made it to the finish line. This was it, and I was so ready. We’d been through a lot together, from all the time spent apart during his Navy years’ interminable deployments to several rounds of breakups and reconciliations during our mid-20s. But we’d been through a lot together mostly by being apart. And being apart, especially when one of you is on a Navy ship in a uniform, gives a relationship the feel of something for the ages. Destiny skulks around a lot. Meant-to-be sounds like a phrase coined just for you.

This is why I was really psyched about this wedding. It would serve as the climax to an epic romantic saga. What had I been thinking, looking at that cocktail dress, staking out mere restaurants for the occasion? Thank god I’d gotten the gown, the marbled Chicago Historical Society with the sweeping spiral staircase for me to walk down, the cake with the raspberry ganache. A day to celebrate the miracle that was us — the triumph of true love over adversity! I couldn’t wait to say our vows before our family and friends — the ones who’d questioned our many reconciliations, who’d wondered if we were too young when we’d met, who’d raised skeptical eyebrows when I passed over perfectly good other men to remain fixated on Dan.

It crossed my mind, briefly, that one of the reasons I wanted this ceremony was to prove to all of them not that love conquered all, but that Dan loved me, that I conquered love. But, no. I loved him, too. Of course I did. Why else would I have kept this going for so many years if I didn’t?

Wedding magazines stacked up on our coffee table, the useful pages (about invitations and favors and placecards, areas I hadn’t yet tackled) dogeared, later to be torn out and fastened into a binder with colored tabs and a personalized checklist I’d typed out myself by combining the pointers in several leading bridal publications.

It is amazing how wrapped up in minutiae one can get when one is avoiding bigger issues, like the fact that one’s fiance has started talking about kids right at the time that one has realized one might avoid them forever. Or the fact that one’s fiance wants to move farther into New Jersey just as one has been overcome with the desire to move into Manhattan at any cost. Or the fact that one has just gotten promoted at one’s dream job, so one is actually writing feature stories for a national entertainment magazine, and one is thinking about writing a book and pursuing new dreams, not settling down with a dog and kids and a yard. Because one spends more time in the city with one’s new group of invigorating, creative, writerly friends than one does at home in Jersey with one’s fiance.

And I defy you to find anything that manufactures obsession with minutiae more efficiently than the bridal-industrial complex. The wedding biz is an insidious ally to the bride who’s determined to ignore her feelings, doing the same job the institution of marriage does for couples who are afraid to think too much: It structures gut feelings out of the picture, gives us steps to follow so that we feel like we’re moving forward with a momentous decision when all we’re doing is obsessing to the point of near mental illness over invitation fonts and frosting flavors.

Even on nights when I found myself with perilously little wedding planning to do — the cake was now ordered, the invitations chosen if not officially purchased — I could scrounge up something to worry about as I sat on the sofa with my binder. I could spend hours, for instance, compiling beauty tips from bridal magazines, even though they were the same beauty tips I’d read a trillion times in women’s magazines (apply two coats of mascara; blot your lipstick) with the bonus implication that this was your one big day ever! What you looked like would never matter as much again! So why not shell out a few grand on a laser treatment, get the extra-expensive foundation primer that doesn’t seem to do much, spring for the hair extensions?

One thought began to haunt my days and nights: What if I got a zit that day? I was fairly prone to them. What if one showed up that day? WHAT WOULD I DO?

I never did come up with an answer. I simply lived in dread.

This OCD phase went on for months, my greatest pleasure in life checking off another wedding-planning step. Then came my bachelorette party.

Now, I don’t mean to disparage it: My friends worked hard on it, and I’d approved all the plans months earlier. We were holding it in June during a visit home sans fiancé — the wedding wasn’t for another five months, but we wouldn’t have time for it then. When I got to my party, I couldn’t help feeling that I was at the wrong place. It was as if a stranger had been the one to approve those plans. A stranger with a nearly-100-percent-checked-off wedding planning list. A stranger who was totally okay with an afternoon bachelorette party that involved a lot of Pampered Chef kitchen gear (complete with special bridal apron), white wine spritzer, and do-it-yourself mani-pedis.

Though it wasn’t even so much the party itself — most of it was like an old-school slumber party, except we were grown-ups so we paid a massage therapist to show up for some rubdowns, which I must admit was great. What got me was the way everyone oohed and aahed when I opened gifts like bath towels and the way people wouldn’t stop asking me about the goddamn wedding, like it was the only thing in my life.

And then it dawned on me: That’s because I’d asked for bath towels on my registry, and because the goddamn wedding was the only thing in my life.

I’d asked for it all, and I wasn’t sure I wanted any of it.

When I returned to New York, I stopped obsessing over my wedding-planning binder. Hell, I stopped looking at it, period. Weekly reminder emails from theknot.com (telling me exactly how long it was ’til my wedding date and which essential tasks that meant I should be doing) dinged my in-box, and I deleted them with only a cursory glance. I was well ahead of schedule anyway, I told myself. I deserved a break. Until, of course, the reminders started to mention things I hadn’t done, like finalize the caterer’s menu or choose favors. I deleted those, too, as if that would delete them from my brain.

Then the bills started pouring in — we owed the rest of the $5,000 for the reception space, $300 for the cake, and a several-thousand-dollar-amount for the caterer (exact total to be determined when I actually committed to a menu). Dan, the one with the checkbook, stayed on top of these things, unfortunately. I couldn’t stay in denial, couldn’t put them off. Those three zeroes on the end of the check to the Chicago Historical Society knocked me dizzy as I put it in an envelope, sealed it, and mailed it under the watchful eye of my fiancé. The cake bill, I couldn’t help noticing, would buy me a couple of good pairs of jeans, an exceptional pair of shoes, or several trips to a couples counselor (especially one covered by insurance). The caterer remained the one realm where I had total power — I was in charge of finalizing menus, so I could decide not to.

I ignored the caterer’s calls, and, incidentally, we tried a string of marriage counselors in addition to ordering the cake. All we got was an old woman who asked us if we were achieving orgasm (listen, lady, if there’s something to achieve, I achieve it) and a man who had the nerve to tell us we were getting old (Dan was now 31, I was 29), so we might as well settle for each other and make things work.

And then we gave up on the counseling. We had a wedding to plan — there was no time to keep up these awkward first dates with ineffective therapists.

Time was, after all, of the essence at this point. We had to order invitations. TheKnot.com had been saying so for weeks. It was pretty insistent about this. Even worse, the personal emails from the nice man at the invitation store were saying so. And they were pretty insistent, too. The last one went something like, “If you don’t confirm your order by this weekend, WE WILL NOT HAVE THEM ON TIME. Unless you’ve changed your date, in which case, please let me know.” He was a soft-spoken, painfully polite man, not someone who would use all-caps willy-nilly. He meant business.

And so it was that I decided to sit down with Dan that crucial invitation-ordering weekend (not a second before) and say, “We should have a destination wedding, I think.”

“We should,” he agreed. I was shocked at how easily this went.

So shocked, in fact, that I said, “Or maybe we should just have the wedding like we planned.”

“No,” he said, “we should have the destination wedding.”

“You’re right.”

“Really?” he said. “Maybe we should just have the wedding like we planned.”

“No,” I said. “Destination wedding.” I was so confused; who wanted what here? No matter, I thought. I had won, hadn’t I? “No more of this silly frou-frou stuff we didn’t want,” I said, genuinely excited about this new plan. “Just us, our families, and a few friends, on an island.”

“Where?”

“I don’t know, the Bahamas. We’ve never been there. It’s like a fresh start.”

“The Bahamas it is.”

And so we ran from the invitation man, from TheKnot.com, from the remaining preparations and the elaborate planning I’d already done, from the thousands of dollars in deposits we’d put down. From the fact that we both knew I didn’t want this wedding. We dashed off a letter to all the folks we’d sent save-the-date cards, telling them to use the date now for whatever they wished but to get ready for a damn good time in the Bahamas … someday … soon.

I told my parents, who were incredibly supportive and understanding, because that is their thing — I was relieved to find the mom I always knew receiving the news, rather than her crazy wedding-gown-and-veil-fixated personality. Dan told his parents on the phone and reported that the news had gone down eerily smoothly. I suspect both sets of parents knew something had been amiss for a while, and had been married long enough themselves to know there was nothing they could do to fix it.

Months passed, brochures were collected, budgets were made, questions were batted away with “we’re working on it.” A destination wedding was not had. It was not even planned.

Then I went to that final dress fitting, and came out with yet another plan: We would get married in Manahattan. We were now moving into the city from New Jersey. We had purchased a condo on the Upper West Side at my insistence, as part of our fresh start, our attempt to bring my diverging identities of Dan’s Fiancee and New York Writer Girl together. Clearly, this was my problem when I was lying to my fellow bride in the dress shop: I had not yet reconciled my identities. But this new wedding plan, by god, might just do the trick.

What better way to celebrate this new life together than to get married in a small park, then hold an intimate gathering at a classy restaurant? Why, New York was full of parks and restaurants! How hadn’t we thought of this before? We would declare our new identity to the world: Here we are, Urbane Power Couple! Surely this was what I wanted. I loved Nora Ephron movies, after all.

But that was just the problem: No matter what wedding I thought up, I seemed to be simply recycling some ready-made fantasy sequence. I was positive I wanted a life in New York — that was the one thing I’d figured out in this mess — so I was trying to make my wedding a part of that. But as it turned out, I couldn’t find much time in my New York life to research those parks and restaurants. I threw out a Google search here, an email there, but when I didn’t get immediate responses, the planning ground to a halt yet again. I printed out a few restaurant reviews, but never got around to visiting the places.

Dan, incidentally, said he’d go anywhere, at any time, and pay anything I needed to get this thing done. He even went so far as to pick an October date (nearly a year after our original date) and write it on the calendar, which his mom found out and helpfully mentioned in her Christmas newsletter to friends and family, which happens to include my parents, who went nuts to hear there was a wedding date they didn’t know about.

That incensed me, but what bugged me even more was Dan’s total capitulation to my demands. I know that seems irrational — ask for what you want, then get pissed when you get it. But suspicion clouded my every thought as he suddenly reversed his earlier wishes to have kids soon, to get a house with a yard and a dog, to have a wife who’d take his last name. Every time he gave in, I didn’t think, “Yay!” I thought, “Really?”

He reminded me of myself, a few years back, when I would say or do anything to stop him from talking about us breaking up to see other people. When I would wish he’d be more affectionate or wonder about our future or just hope we’d go out to dinner instead of staying in to watch Star Trek: The Next Generation … but I would swallow those thoughts, hold my breath, smile and enjoy Captain Picard’s latest adventure for fear of tripping a discussion that would lead to our demise.

I hated myself then, and thinking of it now made me hate him, despite all of my love for him.

In the end, getting away from that former me, in all her forms, became the priority. She would never know who she was or what she wanted — she would only ever know how to be what everyone else wanted. And the path away from her happened to lead the wrong way down the aisle. So that is where I went.

Calling off your wedding sounds big. I would use it, sometimes (and still do) to give people a thrilling little snapshot of me: Instead of being Dan’s Fiance, I am now the Woman Who Called Off Her Wedding. It makes me seem brave and independent and modern. And I like that better than being the girl who did everything she was told.

But the act itself felt more like a billion tiny, excruciating steps — the exact opposite of those brainless, satisfying steps to planning a wedding — every one of which required me to stop, catch my breath, have a sob, look around, find no one there to comfort me, and then do it all over again. Telling my parents, packing up my stuff, moving out of the condo into a low-rent studio in the East Village, explaining the situation to everyone … months of exhaustion. Throwing away my wedding binder for good? My one big moment of relief.

One task sticks in my head as virtually impossible — and I mean physically impossible: taking off my beautiful 1.5-carat solitaire-and-white-gold engagement ring, the one I had once literally quivered with excitement to show off, and handing it to my ex-fiance as I left the condo. Another task remains impossible: taking my wedding dress out of the closet and figuring out what to do with it. It hasn’t left its black garment bag since that final dress fitting.

What if that dress is right, I am wrong, and I could’ve had a life as beautiful as my gown portends? I realize I’ll never know, really. But I do know that I’ll never wear that dress, in that form, at any wedding. I also know, as it turns out, that I don’t reject marriage wholesale, because part of me is still that romantic who believes in a kind of true love. The kind of love that’s truer because both people know themselves, each other, and how insane a proposition marriage is — because they know the artifice of weddings and the institution itself are built to tell us what to want every step of the way. The more you’re thinking about hors d’oeuvres, the less you’re thinking about your own and your partner’s unwieldy life appetites; the more you’re thinking about satin and tulle, the less you’re thinking about losing your own identity to this union; the more you’re thinking about the reception space, the less you’re thinking about where you and your partner are in life, where you’re going together, and whether you want to be any of those places.

I’m also starting — slowly, carefully, mindfully — to envision the wedding I might have someday: an intimate crowd, for sure, that includes my wonderfully supportive family and those amazing writer-crowd people who have become the best friends of my life; a cozy, quiet, cool reception space, probably in New York, definitely with kick-ass food and wine; vows that say something along the lines of, “You’re the best friend I have, you’ve seen me at my craziest and still seem to like me, and you inspire me to be a better person, so, hey, let’s give this ridiculous marriage thing a go.”

Oh, and the dress? I have this little silvery white, Marilyn Monroe number in mind. And I’m confident I’ll find a way to get exactly what I want.

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Jennifer Keishin Armstrong

New York Times bestselling author of Seinfeldia, When Women Invented Television, Sex and the City and Us, & 4 other books. Writing career coach.