Wedding Planning: 100 Days until the Big Day

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It was an unusually warm and sunny day in December when the man of my dreams swept me off my feet, got down on one knee, and asked me to marry him. Or so I’d like to say.



In reality: it was a cold, wet wintery day, I was sick as a dog, and everything that could have gone wrong did. I was drugged up on Muccinex, there was a hair in my breakfast, and there was construction at every turn. Despite several roadblocks in Phil’s romantic attempts, he was able to pull me aside at the South Street Seaport just as the rain stopped and the clouds parted. It was unusually quiet there and free of tourists- undoubtedly because of the weather. My poor, sweet fiancé was nervous as all hell. It clearly wasn’t going as planned. Poor guy.


Photo Credit: JJ Stoner Photography
Photo Credit: JJ Stoner Photography


Finally, he pulled a black velvet box from his jacket pocket, looked at the helicopters taking off in the distance and with a twinkle in his eye and a very anxious laugh, he said: “I love you… hey that could have been us… but that didn’t work out! Anyway, I want to spend the rest of my life with you, whadya think?” I couldn’t help but laugh. I knew what he was doing all along, and here was one of the best public speakers I know struggling to put a sentence together. Needless to say, I said “Yes.”


Photo Credit: JJ Stoner Photography
Photo Credit: JJ Stoner Photography


Since then, it’s been a whirl-wind adventure of wedding planning as my family and I decided to take on the bulk of the work ourselves. While I had no intentions of writing a wedding planning blog, I can’t help but share my secrets, successes, and failures along the way.


Just got engaged? Congratulations! I’m truly so happy for you and excited for this chapter in your life. Here’s what I’ve learned so far about  planning the wedding of your dreams.


Decide What You Want

The first step is to sit down with your future spouse and figure out what you guys want out of a wedding. Do yourselves a favor and don’t invite any friends or family into the initial conversation. Use online resources like The Knot, Wedding Wire, and Style Me Pretty and create mood boards on Pinterest. Start pinning every photo that inspires you, then whittle them down to create a cohesive theme. Think about inside venues versus outside, what your bridal party would wear, what type of food you like, and what you need to make this event reflect you both.

For the record, I found The Knot to be most helpful when making checklists and budgeting, Wedding Wire is hands-down the best for finding reputable vendors, and Style Me Pretty provides the most magnificent inspiration for ceremony and reception styling. You can check out my boards at


Screen Shot:
Screen Shot:


Sit down both families so you’re all on the same page. Tell them what you can afford and let them offer to chip in if they desire. Keep in mind that whoever contributes to your wedding will want their voice heard. At the end of the day it is your wedding, but you need to accept opinions willingly and be able to communicate what you want in an honest but fair way. If you know someone is going to be overbearing, you might want to politely decline their contribution.


Photo Credit: JJ Stoner Photography
Photo Credit: JJ Stoner Photography


Do some research to ensure your vision is within your budget. I had a few things on my board that were much more expensive than I anticipated- it looks like I’ll have to save those ideas for another event! I also originally thought that a wedding at my parent’s farm in rural Pennsylvania would be cheaper than renting out an event space in New York City. Needless to say, we’re building a venue from scratch, and it’s turning out to be about the same cost with a lot more work involved!


Finally, I have been to both extravagant weddings and humble receptions, and I can say with complete confidence: there is no correlation between heavy spending and a successful wedding. What’s more important is that you set the tone. All you really need for a fabulous event is great music, open bar, yummy food, and the people that you love the most.


Phil, my family, and me at my cousin's wedding in Blagdon, UK.
Phil, my family, and me at my cousin’s wedding in Blagdon, UK.

Get Organized

Once you have some direction, you need to get as organized as possible. Pick a date that works for you, your immediate family, and best friends. Then reach out to vendors. One of the things I love most about Wedding Wire is that you can filter your search results. Select the price you are willing to pay for each service and then sort the results by “Most Reviewed.” Contact several vendors at a time, let them know what you’re looking for, what your budget is, and ask for their availability. Choose the vendor that responds the fastest with the most helpful information, and get them on the phone or to a face-to-face meeting. You’re going to be working with these people for months, so make sure you click and communicate well.


Once you’ve got all that under way, check out the rest of my Wedding Planning tips here.

Follow Jess:

Founder • Contributor • Big Sister • Manhattanite • Yorkie Mom • Chocoholic

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