The Best Laid Plans

Posted by on Mar 11, 2019 | No Comments

Jason and Rachel’s love story started when they met in high school. Both of their families moved from areas in Southeastern Wisconsin, to a small town north of Eagle River, hoping for a quieter life. The two new students noticed each other at school, then at church, and before long they were sharing rides to and from school events. While this sounds like the beginning of the romance, it wasn’t. Try as she might, the bubbly brunette with a baby face could not capture the attention of the sports and academics focused Jason.

The pair eventually dated, but decided to part as friends when Jason left home to attend Notre Dame University as Rachel completed her final year of high school.  They both left their Northwoods home town to attend college, and they would see each other when they returned for visits to their families on school holidays. As their lives moved in different directions, Jason became more and more sure the pair were meant to be together. At that point, Rachel, no longer a smitten high school girl, wasn’t quite as certain, but opened the door for the pair to begin anew.

The next few years were a swirl of college graduations, first apartments and first jobs. Jason, an engineer, was working for an iconic Milwaukee company and Rachel was nearing the end of her first semester as a newly licensed high school History teacher. Their adult lives were off to a great start; for Rachel, the next step was clear: it was time to get married. There was just one problem, the couple were not engaged.

Rachel decided to nudge things along by creating a plan that was certain to end with a diamond on her finger. Choosing New Year’ Eve, the night Jason’s parents were engaged so many years before, she created an evening so filled with romance and special moments that she was certain Jason would choose it to ask her to be his wife.

The plan began with a location. Laughing at the memory, she smiled and said, “what’s more romantic than the Pfister?” After checking into the landmark, the pair were off to a dinner at Celia, the hotel’s former fine dining restaurant, named in honor of the beloved matriarch, Celia Marcus. After dinner, the couple then attended a performance of the Milwaukee Symphony Orchestra. Sporting a freshly coifed updo and wrapped in Jason’s grandmother’s fur coat, something the lovely woman insisted Rachel wear, assuring her the fur was exactly what she needed for the special night she had planned, all she had to do was wait for her proposal.

When the proposal didn’t happen after check in, Rachel was not too concerned, the enchanting night she had planned stretched out before them and was filled with perfect moments for Jason to seize. Dinner was delicious, but she did not spot a ring coyly placed in a champagne glass, and soon the pair were finishing the last bites of their dessert. It was clear that there would be no questions popped in the restaurant. It was then on to the symphony, which was a delight, but the final notes of the evening had played and her ring finger was a bare as it was at the start of the night. She felt her frustration grow as she slipped the borrowed fur around her shoulders for the return trip to the hotel.

Back at the Pfister, the couple took the elevator to the 23rd floor to welcome the new year with the other revelers in Blu. The atmosphere was festive and the duo sipped their champagne and watched the city lights sparkle as they waited for the countdown into the new year to begin. As the clock struck 12, the air was filled with cheers and horns, and Jason offered Rachel nothing but a noise-maker and a kiss. Disappointment began to sink in- it became clear they were not getting engaged that night.

Dejected, Rachel trudged back to their hotel room, ready for the night to be over. As they closed the door to their suite, it was the first time couple had been alone, truly alone, all evening. A suddenly nervous Jason reached into his breast pocket and pulled out a small, velvet-covered box. With his now shaking hand outstretched, he offered the box to her. Getting down on one knee, Jason finally asked the question Rachel had been longing to hear. Shortly after, chocolate-covered strawberries were delivered to their room, making it clear Jason had done a bit of planning of his own. The rest, as they say, is history.

All these years later, the Pfister is still a special place for the couple, but now their visits include their two children.  Returning for the holiday events, or just to enjoy a bit of elegance during a hectic week, they remain connected to the place where they began a new chapter in their lives. These days, when they stroll through the halls, they always recall their special night, and it still feels like their very own brand of magic.

Cheers to this, and all of the happily ever afters that began at The Pfister!

Jason and Rachel on their big night, 2002
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