The 4 Hardest Things About Wedding Planning For Me

If I'm being honest, I wrote most of this post about five or six months ago. I wrote it as an outlet for my frustrations with the hardest parts of wedding planning for me, but I decided not to publish it because, while they're all valid, everything was manageable and I was worried about coming across as whining or complaining about everything. As much as these are all true, the planning has mostly been a joy so I didn't want that to be overshadowed by the things I've struggled with.

That said, reading this back over, I'm still feeling these things so I wanted to share. All of these are things I wasn't really expecting to struggle with, unlike the typical big decisions that come with their own baggage (like setting a budget and choosing a venue). Rather, these are the internal struggles that I've been dealing with that no one warned me about.

We're now two months away from the big day and some of these feelings have subsided a bit, but still, here they are:

(This outfit is unrelated, but I need some sort of photos to accompany my complaints)

The Guilt
To be honest, it doesn't take much to make me feel guilty., but wedding planning has really made that part of me even worse. The biggest trigger of this has been the guest list. Like pretty much all couples who plan weddings, we started out saying that we would have a really small wedding (with a 100 guest list), and by the time we sent Save the Dates, our list was at 146 (still not huge, but more than we wanted). Of course, everyone who is on the list is on there because we genuinely want them there, but I've been having such a hard time about leaving some people off. I've gone back and forth on a dozen people, and the fact that we've had to leave some people off was eating at me for a while. I wish there was a way for me to reach out to these people and say "hey, just so you know, we THOUGHT about inviting you and you were really close to making the cut, but ultimately couldn't include you because [we had to cut the list down/we don't really talk as much as we used to/we figured you wouldn't come anyway], but trust me, it's not because we didn't want you there." You know, normal things to say to people out of the blue.

While the biggest offender of causing my guilt has the guest list, it hasn't just been that. I've also felt guilty about choosing a venue that's out of town and the money we have to ask everyone to spend. We've certainly been putting a lot of our own money into this, but weddings are expensive for everyone involved, not just us. There's the money we've asked our parents to contribute (which is a bulk of our budget), the money our wedding party has to spend (attire, shoes, bachelor/bachelorette party, etc.), knowing a shower is being thrown for me, and the money everyone involved has to spend on hotel rooms and (for many guests) plane tickets. And that doesn't even mention the registry/asking people for cash and gifts.

Obviously, I know that I don't need to feel bad about this. People are willing to put in the cost and the effort because they love us, and we've definitely done it for others without complaint. If anything, though, I'm grateful that I feel this guilt because I think it's allowed me to be more conscious about our decisions. We kept this in mind when we chose a hotel for a room block, and we're also making sure not to ask for too much when it comes to things like the bachelor/bachelorette parties and a bridal shower.

The Decisiveness
I always knew that the decision making would be something that I'd struggle with, and for the most part, I've actually been okay with this. I had my fair share of going back and forth with things like the venue, the photographer, and the dress, but I've surprised myself by not letting any of those decisions go on for too long and standing by my choices. Once we got deeper into the decor planning stage, though, I've been having a much harder time. 

I think what I'm struggling with the most is the fact that I only get to do this ONCE. I've, of course, had ideas of what my wedding would look like for longer than I'd like to admit, but now that it's here, I have to make everything count. Do  I go bright and colorful for everything? Soft and vintage? Fun and retro? Whatever I decide, I have to stick with it. There are no do-overs or second weddings in the plan (no judgment to anyone who's gotten married more than once, but I'm obviously not going into this expecting a second wedding my future!). 

I know that I'll feel happy with all of my choices in the end, but it's difficult not to feel that pressure. 

My Identity
Buckle up, because this is a complicated one that stems from my minor anxieties and overthinking. As we've been planning this, I've felt this overarching pressure for the wedding to feel like "me" or at least what people expect of me. Where this has been the hardest has been the dress. I was absolutely positive that I was going to choose a short, retro wedding dress, but when I tried on long ones, I became evident that I needed to take this chance to wear something so special and unlike what I would wear every day. I am SO in love with the dress I found, and I don't regret it at all, but there's still this little part of me that can't get over that I'm not doing what I expected. 

I think a lot of people in the vintage community feel this in their every day lives, but there really is this pressure to be "vintage" every day that we put on ourselves. It's completely internalized and even though people I've told are certainly surprised that I'm not wearing a dress like they expected, it's not like anyone is going to be disappointed with me.

The Control
I've always known that I'm a control freak and capital Type A, but oooh boy, has wedding planning brought that out in full. I've felt like a lot of things I've asked other people to do has either not gotten done or it's been like pulling teeth to get them done in time. Because of that, I've had a hard time asking for help. Now that we're getting so close, I've been trying to be better about asking a couple of people I trust to help with certain things, but it's been really hard letting go sometimes. It's been so nice to have everyone ask me what I need, but I've just been finding it a lot easier to do things myself. Granted, this is absolutely a weakness of mine, not a strength. I've made the mistake of making some decisions without Jon because of this, but I've been trying to learn from that and be better about making sure he's involved in everything. It's a learning process!

If there'a theme to all of my struggles, it's that it hasn't been easy for me to remember that this is just mine and Jon's day, and no part of this needs to be what anyone else wants or expects. I'm thankful that Jon DOES have an easier time with that concept, and he's reminded me of it every chance he gets. 

I do want to make this clear: all of these things are manageable and while these issues have come up here and there for me, I really am loving the process overall. I'm not writing this for anyone to comfort me or to tell me not to feel bad, I'm writing this because it helps me to put these thoughts into writing and because I know I have a lot of engaged friends who might be dealing with some of the same things. Every time I get stressed about something, I've been making it a point to remind myself: the only thing that matters is that I get to marry Jon. Even if things aren't exactly like my vision or anyone gets upset about not being invited, as long as Jon is there and we get to marry each other, it will be a perfect day. 

Outfit Details
Dress: vintage via Fly Lark Vintage
Cardigan: MAK Swater (use code Elana-yemak-010 for 40% off)
Shoes: BAIT Footwear
Belt: Modcloth


  1. I am so glad you shared this!! We are having a destination wedding and even though we're keeping everything else very chill, I'm still having weird guilt issues about asking people to make a big trip!

    Priya the Blog

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  3. I felt much the same way about the dress I chose, not because my typical style is vintage but because the wedding dress I loved didn't align AT ALL with my usual style. I knew exactly what sort of dress people would expect of me, & quite honestly, it was what I expected of myself - & then I fell in love with this long, ornate, princessy dress that felt ridiculous & out of character, but I loved it SO MUCH that I had to go with it anyway. And you know what? I looked bomb on my wedding day - not a regret to be found. Hope it's the same for you. <3

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  6. Your positive outlookon the toughest aspects of wedding planning is truly inspiring