Self Love

14 Lessons on Life, Love and Breakdowns: What Throwing 3 Weddings Taught Me

April 22, 2015

Before I met my husband, I was never the girl who dreamed about her big white wedding and her diamond ring. Actually, when I first met my now husband, I had been single for four years, was loving life, hustling my butt off building my career during the day and hanging out in hipster dive bars with my beautiful and fabulous girlfriends at night. (Like, until the lights would come on.) During that time, I had come to love and appreciate the pure bliss of freedom. The word “boyfriend” terrified me.

Falling in love with Brian was so natural, so unexpected and so deeply gratifying. He was the polar opposite of what I thought my type was. I was used to being in toxic, co-dependent relationships with emotionally crippled men. Brian taught me that kindness, consistency and emotional availability could be sexy. Super sexy. We got set up on a blind date, and it lasted six and a half hours. From that night on, it was game over. I knew right away he was going to change my life, and me his.

(Lesson #1: Single girls, this one’s for you. Don’t limit yourself by a “type.” “Nice guys” all have an edge too, and it’s hotter than you think.)

Flash forward almost three years later, and we just wrapped what we called our “Wedding Trilogy.” That’s right, I didn’t throw just one wedding. I threw three.

Let me explain…

Since Brian and I chose to throw our wedding in Mexico, we couldn’t legally get married there, so we intended to go to the courthouse in Chicago, just he and I, and make it official prior to leaving for Mexico.

Enter my Jewish mother. She was adamant that Brian and I get married by a rabbi. We agreed. Not only to appease my mom, but because I am a person who is led so deeply by faith and spirit, and my roots matter.

(Lesson #2: When throwing a wedding, your family is going to project their own feelings and agendas onto yours. Make your decisions with love and respect. Remember that being “agreeable” isn’t a sign of weakness. It’s actually a sign of class, humility and strength. )

On January 17th, 2015, our immediate families and those that couldn’t make the Mexico trip gathered at the house I grew up in. My mom and dad rented a chuppah (and set it up themselves while crying tears of joy), Brian’s best friend brought in a case of wine and we catered in the most delicious kosher food imaginable. We called this night our “First Wedding.” Our Rabbi Michael Sommer, (who has become our friend and one of the biggest gifts in our marriage journey), gave a flawless Jewish ceremony rich with history and personal stories. The whole house was in tears. It laid the foundation of our marriage, not only because it was legally binding, but because it was so intimate, so sacred and so meaningful… My parents got married in their parent’s house by a rabbi over 44 years ago.

(Lesson #3: Weddings elevate and amplify the meaning and holiness of traditions. Follow them if you can.)

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Onto our Second Wedding…

While I never dreamed of a big white wedding, I did dream of an intimate destination wedding with only immediate family and closest friends at my favorite place on the planet, Zihuatanejo Mexico. We hosted our wedding weekend at one of the most magical, breathtaking, luxurious hotels in the world, La Casa Que Canta (which means “The House of Music). Why this place? Because my family and I have been taking our annual holiday vacation here since I was 16 years old.

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(Lesson #4: Weddings are an exercise in vulnerability. So in the spirit of bearing it all, here is an excerpt from my vows…

You could say I grew up on the beaches of Zihuatanejo. Since high school, through all my heartbreaks, drama and dreams, I could never have fully pictured this moment until there was you. You have made everything real. A love, a friendship, a partnership, a family. It’s all real now. It’s in color.”)

While it’s literally impossible to explain what those epic four days looked like and felt like, I’ll try…

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On January 31st, 2015, we held our personalized ceremony against the rocks of the ocean (my younger brother was our officiant), full of colorful, vibrant florals (I chose this color palette because I wanted it to represent life and love…messy and imperfect and beautiful). We rented out a 15,000 square foot private house for four days, complete with a private chef, butler, maid and house hostess, and we held our reception there. My DJ Jesse Hozeny said he felt like he was in an episode of MTV’s Cribs. 

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We served a five-course, five-star dinner with fine wines and even finer tequila.

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After the speeches were read, the bread was broken, the dancing was in full swing, we all changed into our bathing suits and jumped into our villa’s private pool. That’s right: my wedding turned into a midnight pool party.

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My mom said at the end of the weekend: “One day, your wedding will become an urban legend.”

(Lesson #5: Mother’s are usually right.)

Our third and final wedding took place just this last weekend on April 18th, 2015. Brian and I are so blessed with so many friends from all different chapters and parts of our lives, and our parents are blessed in the same way. And so in honor of this abundance of family and friendship, we threw a big, cocktail-style, dance bash for 250 of our favorite people in the Penthouse Ballroom of the Wyndham Grand Riverfront Hotel.

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There was no sit down dinner, no stuffy centerpieces, no long cheesy speeches: just amazing music from the Gold Coast All Stars, lavish hors d’oeurvres and super strong cocktails. (I didn’t even wear a dress but rather a pair of Badgley Mishka palazzo pants, an Alice+Olivia corset and a pair of white, sparkly Nike Sky High Dunks.)

(Lesson #6: On your wedding night, wear what makes you feel beautiful. However, don’t underestimate the power of being and feeling comfortable. It’s your night. Make your own rules.)


Brian and I really didn’t think it could get any better after Mexico, but Saturday night proved us wrong. Our family and friends brought their A-Game, danced like fools and embraced and celebrated our marriage with so much spirit, joy, love, light and enthusiasm. We are still buzzing.

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(Lesson #7: Weddings are so much more than just a party. If you can tap into the energy contained in that space, energy that is being created just for you and your partner, it has the potential to elevate your ability to love, to feel and to experience being in the present moment. It’s better than any drug in the world.

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(Lesson #8: That feeling is as fleeting as anything. It will all go by faster than you could possibly imagine, so hold on to it. Most of all: enjoy it.)

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I know it sounds like our Wedding Trilogy was practically perfect. And it practically was. However, there were some downfalls throughout our #BFANDJZ journey that hurt to think about. Some of these mishaps were more significant than others, but they still left lessons in their wake, nonetheless.

During Wedding #3, Brian and I wanted to dance the Horah. Apparently, not everyone else did. When the band starting playing “Havah, nagila, havah!” only a fraction of our guests formed a circle and all of the strong men we assumed would lift us up in the chairs – bolted. We just sorta stood there waiting for someone to come to our rescue for what felt like forever. Eventually, my baby brother summoned as many dudes as he could rapidly gather to lift up our chairs. It was awkward. Very awkward.

(Lesson #9: Embrace the awkwardness.)

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Perhaps one of the hardest parts to my past year had to do with my best friend. Hedy and I have been friends for 31 years. She’s the closest thing to a sister I’ve ever had. I knew she would be my maid-of-honor since we were in elementary school and the second I got engaged, I asked her to stand by my side in Mexico. The second I got engaged, Hedy and her amazing husband also got pregnant. Five months before my wedding, Hedy sat me down to tell me she wasn’t going to be able to make it to Mexico, as she didn’t feel comfortable flying to a foreign country when she would be seven months pregnant with her first baby. While I of course understood, and couldn’t be happier that my best friend is a new mama (baby Maya was born yesterday at 7.2lbs!!), her absence devastated me. For 30+ years, I expected the sun to rise, the sun to set and for Hedy to be at my side on my wedding day. She wasn’t. And you know what? It was okay. My wedding was amazing, Maya is perfect and Hedy and I are stronger than ever.

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(Lesson #10: Relinquish control. The world does not revolve around you or your wedding.)

Final tidbits of advice on wedding planning:

(Lesson #11: Throwing a wedding without a Wedding Planner is like checking into a hotel for a week with no bathrooms. Rachel De Marte is the best in the business. I have never seen anyone as capable of managing every single last detail as she is. Rachel was literally the oxygen to our Trilogy. We couldn’t have survived without her.)


(Lesson #12: Invest in a great photographer and a great filmmaker. Brian Carey and James Gustin of Fig Weddings are artists, and not only captured the aesthetic beauty of our moments, but the essence of Brian and I, and our love. Some say love lasts forever. (I agree.) But so do pictures and video. Spend the money. You won’t regret it. (More of Brian Carey’s photos and the wedding film created by James Gustin can be found here.)

Final tidbits of advice on life:

(Lesson #13: Take nothing personally. Like I said earlier, throwing a wedding makes you feel really vulnerable. Some people won’t be able to attend your wedding. Some people will back out last minute. Some people will leave early. Some people will RSVP and then won’t show up. Everyone is inside their own lives and doing the best they can. Your wedding is simply a moment in time when everyone and everything is supposed to intersect. And because people are all on their own journeys too, it’s never going to be and look like just what you want. Let it go. Be in the moment. It’s yours. And that’s all that matters.)

Final tidbit of advice on love:

(Lesson #14: Whether you throw one wedding or eight, if you host 500 people, or if you host five, getting married is about only three things. You. Your partner. And the love you share. The wedding is just the beginning. Marriage rocks.)

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  • Stuart Walker

    Beautifully written. Reminds me of our wedding (we had 2) and after almost 3 years of marriage; why love, my partner and the love we share is what keeps our marriage strong