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Bride: Jenna Flack, 33, Consultant

Groom: Dalio D’oleo, 37, Program Manager

DATE: April 5, 2024

VENUE: Enigma Cocktail Lounge & Wine Vault, Washington, District of Columbia (D.C.)


The Beginning

Dalio and Jenna’s love story is straight out of a romance novel. It all started on September 5, 2021, at a Labor Day family gathering in quaint Stafford, Virginia. A friend of Jenna’s brother-in-law, Dalio, found himself amidst the festivities and crossed paths with Jenna. Little did they know this chance encounter would set their hearts on fire.

Fast forward to December 19, 2021, when Dalio and Jenna had their first date at the cozy Po Boy Jim Bar & Grill in lively Washington, D.C. They opted for brunch, Jenna’s all-time favorite meal, and it was the perfect choice for a relaxed and delightful time together. What’s more, it was Dalio’s very first brunch experience! Jenna’s idea of adding a New Orleans flair to the brunch gave the date a thrill.

I Love You

It was a heartwarming moment when Dalio finally gathered the courage to tell Jenna, “I love you,” after 4 months of dating. The best part for him was seeing Jenna’s face light up as she immediately reciprocated the love. Jenna adores Dalio for his integrity and reliability. She said, “he’s the kind of guy who sticks to his word, stays committed, and is always there for his loved ones.” He makes Jenna feel incredibly loved, secure and understood.

On the flip side, Dalio can’t help but be in awe of Jenna’s unwavering determination. He genuinely believes she’s the most inspiring person he’s ever met. Her drive to achieve her goals – whether at work, in the gym, or experimenting with new recipes in the kitchen – truly motivates him. He feels incredibly fortunate to have her and can’t wait to call her his wife. Their love story is one for the books!

Surprise Proposal

At the breathtaking London Eye in London, England, Dalio proposed to Jenna on November 1, 2023. The London Eye, the Millennium Wheel, is Europe’s tallest cantilevered observation wheel, offering stunning city views from the South Bank of the River Thames.

Jenna described the proposal as absolutely magical. It took place during their first trip to Europe. On the second day of their journey, Dalio surprised her with a champagne experience, a ride on the London Eye, and a city cruise. Despite the rain and his noticeable nerves, she assumed his anxiety was related to the giant wheel and the rainy weather. Little did she know, he had something extraordinary planned. When they reached the top of the observatory, he asked the attendant to take their picture, but in reality, he was setting up to record the proposal. Jenna was utterly stunned, standing frozen, with her jaw dropped, holding a glass of champagne and eyes wide with astonishment. Of course, she said “absolutely yes,” it was the most incredible and unexpected engagement experience. As they left the pod, two women approached them and shared that they had witnessed the proposal from their observatory pod before kindly offering to email them the photo. Their celebration of the engagement continued in Venice, Italy.


Dalio’s expression of love for Jenna was nothing short of extraordinary. He presented her with a breathtaking 1.31-carat cushion cut diamond engagement ring delicately placed on a stunning yellow gold Gabriella Pave Hidden Halo setting. 


Dalio and Jenna had a clear vision for their engagement photography session: they wanted it to be fun and exude an editorial, moody vibe. As an adventurous couple with a shared love for exploring, wine, and whiskey, they aimed to capture their dynamic personalities and passions in their photos. Their session was split into two distinct parts: a sultry bar scene and a romantic sunset stroll through the vibrant streets of Washington, D.C.


Dalio and Jenna had the excellent idea to incorporate some of their engagement photos within the captivating ambiance of Enigma Cocktail Lounge. This stylish lounge boasts a unique, moody atmosphere with its opulent décor, plush furnishings, and subtle lighting, creating an inviting setting. The ambiance captivated the couple, and they were equally impressed with the delectable food and exquisite cocktails. The hospitality extended by the team at Enigma made their experience even more delightful, making them feel right at home. So much so that they returned aftertheir photo session and had a fantastic time. Undoubtedly, Enigma Cocktail Lounge was the perfect choice for a memorable photo session and romantic date night.


Dalio and Jenna were all about dressing to impress for the Lounge photography session. Jenna rocked a stunning white Body Con dress with sheer sleeves and a turtleneck detail from House of CB. To top off her look, she added chic gold studded earrings and slipped into the “Glacier Glass Slipper” designed by Jennifer Le. These shoes were like a modern-day Cinderella glass slipper adorned with dazzling crystals. It was a fashion fairytale come true!

Dalio looked sharp and stylish in his charcoal black 2-piece suit from Men’s Warehouse, paired with a sleek Lands End black turtleneck made from Supima cotton. He added a touch of sophistication with a yellow gold chain over the turtleneck and a striking black and yellow gold Movado watch. His look was completed with black leather Cole Haan Hawthorn Oxford shoes, making a lasting impression.

During their leisurely stroll through the streets of D.C., they opted for a relaxed photography session. Dalio sported a stylish caramel-colored corduroy jacket from Gap paired with a white tee and Air Jordan 13 Retro Wheat sneakers. He completed his look with a yellow gold chain and a sleek yellow gold Movado watch. 

Jenna selected a cream top and a cropped bomber jacket to complement the golden hour lighting. She paired them with acid-wash high-waisted jeans and added a Louis Vuitton Reversible Belt to complete her outfit. Dalio also surprised her with a matching pair of Air Jordan sneakers to wear during the photo session, adding a sweet touch to her look.


Dalio and Jenna said, “We have realized that a wedding reflects the couple and their love.” “Following your heart and planning for what feels right is important. Your happiness will be contagious, and those who love you will share your joy. It’s a wonderful reminder to stay true to yourselves while planning your special day.”


Dalio and Jenna are thrilled to share the fantastic news that they are planning a beautiful and romantic wedding in October 2024. They have enlisted the help of Fawne Lindsey, a talented wedding planner, to help them finalize the perfect wedding location. After the wedding, they are excited to embark on a dream honeymoon to explore the enchanting cities of Paris, Madrid, and Barcelona!


VENUE: Enigma Cocktail Lounge & Wine Vault – @enigmaloungedc

PHOTOGRAPHY: Karen Gage Photography – @Karengagephoto

RING: Rare Carat – @rarcarat


Dress: House of CB – @houseofcb

Top/Jeans: Amazon – @amazonfashion

Belt: Louis Vuitton – @louisvuitton

Shoes: Jennifer Le – @iamjenniferle

Jewelry: Zales – @zales

HAIR: Dommie Cole – @idommiecole

MAKEUP: Rhiana Dion – @rhiana.dion


Suit: Men’s Warehouse – @menswearhouse

Shirt: Lands End – @target

Watch: Movado – @movado

Shoes: Cole Haan – @colehaan

Jacket: Gap – @gap

SNEAKERS: Nike Air Jordan Retro 13 Wheat- @nike

RESTAURANT: Po Boy Jim Bar & Grill, Washington, D.C.

WEDDING PLANNER: Fawne Lindsey – @rsvpwithfawne

If you are planning a wedding in Roanoke Virginia, Richmond Virginia, Fredericksburg/Northern Virginia, The Shenandoah Valley, Coastal Virginia or in Charlottesville/ Lynchburg Va. we can help with your wedding planning and ideas.

The author: Debra Shepperson

Debra is a native of Virginia, having lived in both Roanoke and Richmond. She is the co-owner of Relish – Say I Do!! Officiant & Photographer. She is an artist who aims to create ceremony scripts and capture photos that evoke positive emotional responses, inspire others, and deliver nostalgia. Debra holds a graduate degree from Virginia Commonwealth and an undergraduate degree from Saint Leo University, Florida. Before gaining more than ten years of wedding-related experience, Debra was a human resource executive. She has been happily married to the co-owner of Relish for more than 20 years.