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September 19, 2026
Pontiac, MI

Bailey & Matthew

We're getting married!

Matthew Dempsey

and

Bailey Williams

September 19, 2026

Pontiac, MI
88 days88 d21 hours21 h32 minutes32 min23 seconds23 s

The Start of Us

2021

After two weeks of being stuck inside with COVID, Bailey was more than ready for a night out when her friend Lauren invited her to join her brother and his friends. Little did she know, that night would change everything. The moment Bailey laid eyes on Matthew, she turned to Lauren and said, “Uh oh… he’s going to be trouble.” The two didn’t talk much that night until Bailey realized she might have locked her keys in her car. Out of nowhere, Matthew appeared, scolding her (in the most charming way) for leaving her purse inside and walking her out to check. Her keys were safe, but her thoughts about Matthew lingered the entire drive home. That first encounter stuck with them both. Matthew went home telling everyone he had just met “the one,” while Bailey couldn’t shake the feeling that something special had begun. Over the next few months, their paths kept crossing, the conversations and laughter grew, and the flirting became impossible to ignore. Six months later, Matthew finally asked Bailey out and from that moment on, they’ve been inseparable.

The Perfect "Yes"

2025

After four wonderful years together, Matthew knew it was time to make it forever. With the help of his mom, Karen, he started planning the proposal in late June. Once he found the perfect ring he knew Bailey would fall in love with, he asked her dad, Al, for his blessing over Fourth of July weekend. Let’s just say Al’s reaction was one for the books (a near heart attack in the best way possible). Because Bailey has a sixth sense for surprises, Matthew had to be strategic. Together with his mom and sister, he came up with the perfect plan: they’d have Bailey and Karen “throw” Matthew a surprise 30th birthday party. What Bailey didn’t know was that she was actually planning her own engagement. Bailey picked the date, help plan the food, and spent the night before decorating and setting everything up completely convinced she was about to pull off the ultimate surprise for Matthew. The next evening, as they arrived and turned the corner expecting family to yell “Surprise!” Bailey was met instead with a stunning proposal setup straight out of a dream. After four years of love, laughter, and growth, Matthew asked the question Bailey had been waiting for and she, of course, said yes. The “birthday” turned into the beginning of forever.

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