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Ashley & Thomas

May 25, 2025 • Kohler, WI

Ashley & Thomas

May 25, 2025 • Kohler, WI

July 2020

In the midst of summer 2020, Ashley had created a Hinge account to entertain herself alongside her girlfriends. The men of the internet were a fascinating bunch, with their strange pick-up lines and quirky hobbies. Ashley and her friends had a blast exchanging screenshots and stories.


Ashley was scrolling through her Hinge messages one morning, when she saw a new one from Tommy Welch. He had sent her a simple request: "Can I get a pic of you?" Ashley rolled her eyes and felt a wave of nausea. "Gross, what a creep," she thought. She decided to play along and replied, "What for?" Tommy wasted no time and sent her his answer: "So I can show Santa what I want for Christmas this year." Ashley couldn't help but chuckle at his cheesy line. It was lame, but also kind of cute. Maybe he wasn't so bad after all.


After Ashley's plans had been canceled a few days later, she messaged Tommy asking if he would be interested in going out to dinner that night. Tommy eagerly said yes and chose Cooper's Hawk as the place to impress Ashley.


Tommy arrived at the restaurant early and waited outside. He texted her to let her know that he had arrived. Ashley, on the other hand, was still in her bathroom getting ready for the evening. She glanced at her phone and saw Tommy's message. She felt a pang of guilt and anxiety. She quickly replied, "Sorry, be there soon."


As Ashley approached the restaurant, she spotted him standing outside. Ashley felt her heart skip a beat. She was hopeful that this attractive man outside was Tommy. After asking, "Hey! Are you Tommy?" She was delighted to find the answer was yes.


Once they were seated, Ashley and Tommy had spent so much time getting to know one another that Ashley had forgotten to look at the drink menu. When the waitress came to take their drink order, Ashley was not a wine connoisseur at the time, but she knew she liked a sweet and fruity wine. She racked her brain for the name of the wine she had enjoyed before, but all she could recall was that it began with an M. She decided to take a guess and ordered a merlot, hoping it was the right one. She soon realized her mistake, as the wine was dry and bitter. It definitely was not the moscato she knows she loves now. She barely touched it throughout the dinner, preferring to focus on the food and the conversation. By the end of the date, she still had a full glass of merlot left. She didn't want to waste it, so she gulped it down in one go. She felt a warm buzz in her head and a flush in her cheeks. Tommy smiled and knew that was his type of lady.


The evening had flown by in a blur of laughter, sparks, and wine. Ashley and Tommy felt a connection like never before. They walked out of the restaurant and to their cars. After a hug, Tommy promised to call her soon. They both drove away smiling, feeling a mix of happiness and longing. Tommy then immediately called groomsman, Trenton Jordan, and said, “Pop, I’m gonna wife that girl up”. They couldn't stop thinking about each other, and they counted the minutes until they would meet again.

The Engagment

Picture of The Engagment

Tommy had a secret plan for Ashley’s Birthday. He had already taken her to Carnivore, the steakhouse they both enjoyed, but he told her that was just a warm-up. He had something even better in store for her for the following weekend.


On the night of April 28th, they had reservations for dinner at Harbor House on the lakefront in Milwaukee. Like the previous weekend, Ashley thought this was to celebrate her Birthday.


On the way there, Tommy missed his exit on the freeway and wound up on the home bridge. This was odd considering Harbor House was somewhere they often went to celebrate special occasions. Ultimately he was just nervous about everything he had planned.


Once they finally arrived at the restaurant and were about to drop off the car at valet, Tommy pretended that he had messed up the reservation time and he suggested they take a walk on the lakefront to pass the time.


Ashley was a little suspicious after they started walking out. She looked around, searching for any clues of a hidden surprise. Luckily there were several people down at the lakefront to take prom pictures that time of the year. Still, she saw nothing unusual. They were going on a Caribbean cruise a few weeks later and Ashley was convinced he was proposing then anyways. Suddenly, Tommy pointed at something behind Ashley and said, “Hey, what’s that?” Ashley turned around, hoping for a surprise of some sorts. But all she saw was Discovery World.


As her eyes searched for what Tommy was pointing at, she heard his voice showering her with compliments and she spun around swiftly. Tommy started to get down on one knee. He was beaming and saying the most sweet and sincere words she had ever heard. With a photographer at the ready, he asked her to marry him. She gasped and felt tears in her eyes. She said “Yes!”


They spent the rest of the night celebrating. First, with dinner at Harbor House and second, with yet another surprise up Tommy’s sleeve, a small engagement party with their closest friends and Boone and Crockett.


The surprises weren’t over yet. At dinner, Tommy had mentioned he booked a weekend trip to Chicago for the two of them to enjoy and celebrate the next chapter of their lives.


Nothing could compare to the joy of their engagement and the start to their happily ever after!