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Bryn Anderson & Kyle Massey

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We're getting married. FINALLY!

Leaves and LightsLeaves and Lights

Kyle Massey

and

Bryn Anderson

May 25, 2025

Madison, WI
16 days16 d13 hours13 h6 minutes6 min28 seconds28 s

How We Met

Love at First Fishbowl

Kyle and Bryn met while working at the legendary Wando's Bar and Grill in Madison, WI. Your typical bartender/bouncer love story... these two started off as coworkers and friends bonding over their love of dogs and sports. Kyle fell for Bryn's incredible dance moves and work ethic while she fell in love with his stories and flowing locks of hair- his dog Lexi also sealed the deal. Fast forward to almost 9 years later, these two have always been soulmates and are so excited to celebrate the way they've always wanted with the people that mean the most to them!

How Kyle Proposed

8/11/2023

While Kyle has asked Bryn casually at least once a week to marry him since they started dating in 2016, he officially asked on 8/11/2023 on a trip to Nashville, TN in the intimate setting of their room at the Moxy Hotel. Leading up to the weekend getaway, Kyle was especially excited about their trip. Bryn just thought it was because Kyle had not been to Nashville yet and was looking forward to listening to some live music, little did she know he had bigger plans in store. Christmas of 2022, Kyle asked Bryn's dad Steve if he could have her hand. According to Kyle, Steve's face looked terrified when he began asking as everyone knows Kyle isn't a serious person. According to Steve, he says "I knew what he was asking and of course I was going to say yes but I should have made him sweat more haha". Flash forward to August 11th 2023, as Bryn was FINALLY finished getting ready, Kyle stopped Bryn and said: "I have one more thing to tell you before we leave..." Bryn's face was also terrified (just like her dad's face) as Kyle was shaking- so Bryn thought he forgot his wallet or something crazy. He continued and said ".. I never want to call you my girlfriend ever again".. and got down on one knee with the ring box. He said some other stuff but neither one remembers haha. Kyle stayed on his knee far too long, in which Bryn repeated "I said YESSSSSS", in confusion, Kyle looked at Bryn's left hand and saw the ring already placed on her finger, in which he replied, "You snatched that ring up so fast I was confused why you already had a ring on". They spent the rest of the night in Nashville celebrating with their best friends Chris and Kelsie.

The Ring

Bryn always wanted a family heirloom as her wedding ring- something sentimental and full of love. Kyle spoke with Bryn's parents and decided on her Great-Grandma Fran's wedding ring- almost 100 years old and a successful and loving marriage of over 30 years before Great-Grandpa Stan's passing.

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