Lisa & Thomas

Lisa & Thomas

October 18, 2025 • Holyoke, MA
Lisa & Thomas

Lisa & Thomas

October 18, 2025 • Holyoke, MA

“Want to ruck up a mountain with me?”

Picture of “Want to ruck up a mountain with me?”

The adventure of Lisa and Tom began in 2020 when Covid was in its peak. While the world was shutting down, both Tom and Lisa found themselves downloading dating apps. Lisa was swiping one day and came across Tom who had “super-liked” her and seemed pretty cute and interesting, so she matched with him. Tom knew exactly how to start winning Lisa’s heart by starting the conversation asking about spartan races and Scooby. They immediately hit it off and soon enough a mini golf first date was planned.

The mini golf date took place at Farmington mini golf where Lisa arrived 15 minutes early because that’s just who she is as a person.
Tom, on the other hand, miscalculated the drive and ended up being 20 minutes late (which Lisa still likes to remind him about to this day haha). Luckily Lisa really liked him so she waited and she’s glad she did! They had such a good time mini golfing and Tom quickly learned how competitive Lisa is. There is an ice cream parlor attached to the mini golf course which most would think would be the perfect way to end the date. However, ice cream loving Tom knew that Lisa likes to be healthy so he wasn’t sure if he should ask to get ice cream. Instead, the two of them just sat outside the ice cream parlor and chatted for the next hour. So, while Tom was secretly sad he didn’t get his ice cream (which Lisa totally would have been down for!), they still had an awesome first date and knew more would come.

After a couple more simple dates and Tom meeting Scooby (who approved), Lisa wanted to see if Tom truly was into hiking and mountains, so she planned some big adventures. Those who know Lisa know that she doesn’t pick easy hikes and she likes incline…so the first was a ruck up Mount Greylock on Labor Day weekend with Scooby joining along too! The first 3 miles of this hike was all uphill with Lisa saying “I think it’s just one more left then almost there”. She said this at least 5 times ha! While Tom may have been struggling, he never let it show. He crushed the hike while carrying weight in his backpack and they enjoyed a lovely picnic at the top. That’s where they took their first selfie together with Scooby in it too!

photo

Next up was the big one…Killington! Spartan races were still canceled from Covid but Lisa wanted Tom to experience the infamous Spartan “death march” there, so they planned a trip up to VT to ruck the death march and enjoy the fall foliage. The hike went wonderfully. Tom conquered the death march and they got to take in the amazing views together at the top. Lisa told Tom right then that “next year when spartan races are back we will run this course together” (spoiler alert: they did!). And, as they drove home from VT on 9/20/2020, they officially became a couple and realized that was just the beginning of their numerous adventures together!

photo

Continuing with big events happening on mountains…Lisa and Tom were at Lake George with some friends for a long weekend in June. While there they decided to hike up Prospect Mountain which was walking distance from their cabin. On 6/4/2021 they hiked all the way up to the top of the mountain. That is where Tom told Lisa, for the first time, that he loved her and she said she loved him back! It was a good day!

photo
photo

Over the next months Lisa, Tom, and Scooby traveled all over doing hikes and spartan races and having so much fun. But, they still felt like they were missing something. That was until fall 2021 when Tom and Lisa were at Cabela’s and saw a German shepherd puppy and immediately got puppy fever. Lisa had always wanted to get Scooby a dog sibling but the timing never felt right until then. Within a week of seeing that puppy Lisa and Tom were looking at puppies for adoption. They stumbled across a 2 GSD mixes, one called “Rooster” and one “Mai Tai”. They got approved for both so Lisa left the decision up to Tom and he picked “Rooster” (who Lisa was leaning towards too), so “Rooster” it was! After seeing pictures of him from his foster house they decided Bandit was a more fitting name for him and on 11/19/2021 Bandit officially joined the pack! At that point Lisa and Tom knew they were both serious about building a life together.

photo

Tom officially moved into Lisa’s house shortly after getting Bandit (though was basically living there at that point), but they knew ultimately they wanted to get a bigger house together. They both always dreamed of having a house with a huge backyard for the dogs to run around in, host summer cookouts, and could also fit Lisa’s outdoor obstacle rig. They started looking for houses together at the end of 2022 and came across one that had their dream yard and was in a good location. On 2/22/2023 they closed on their first house together as a couple, where they would plan to build their future life together! Both dogs approved with zoomies around the yard!

photo

At that point it was pretty clear that Lisa and Tom were in it for the long run. Both of them loved each other and they had discussed eventually getting married. Lisa and Tom both started to have other friends getting engaged and getting married and Lisa started to get antsy. She didn’t think she’d be that girl, but she started secretly picking out a ring she liked and jokingly let Tom know what friends knew that info. She started not so casually sending Tom engagement memes to drop hints. While Tom made it seem like he wasn’t getting the hints, he was secretly scheming!

Jump to the day before Christmas Eve (Christmas Eve Eve) where Lisa and Tom went out to breakfast and Lisa was telling Tom how the ring she likes had a 13 week turn around time and how if he ever planned to propose he couldn’t plan a hike or she would be suspicious. Little did she know, the ring was in the backseat of his car (which she even threw her gym bag on without seeing) and he already had a plan in motion. He had gotten the ring details from her BFF (and maid of honor) Vickie’s husband, Geoff. Tom and Geoff knew Vickie would potentially spoil it so they teamed up to get the info from Vickie’s phone so Tom could order it. They succeeded! Both Vickie and Lisa were clueless!


To keep the proposal a surprise, he worked off of a hike Lisa had already planned for Christmas Eve with the dogs up to Heublein tower. He had reached out to her friend (and one of her bridesmaids), Melinda, who is a photographer and likes to hike and let her know his plan. He had her hike up the tower from the main trail (Lisa and Tom were coming up the other way) and hide out to capture the moment. Tom’s planned worked perfectly and Lisa had no suspicions. She did think it was weird he asked like 6 times what the hike location was and what the parking lot and trail looked like but she didn’t piece it together. She really had no idea starting that hike that she was about to be engaged by the end of it. The dogs had no idea either!

photo

As they made their way to the top of the mountain Tom was adamant that they take their break by the tower. This also went over Lisa’s head but she continued on to the tower. Lisa set Tom up for the perfect moment to propose when she turned her back to him to take a picture of the dogs with the tower in the background. As she finished taking her picture Tom told her to look what he found and as she turned around she was completely surprised. Her face in the picture captured shows how baffled she was! It took her at least 20 seconds to process what was happening but once she did she quickly said yes!! They kissed and celebrated and the dogs were excited too!! 


Tom thought at that point Lisa would cut the hike short to go home and celebrate but in true Lisa fashion she wanted to hit her mileage so they still did the full hike, now as an engaged couple, and then went on to tell all their family members who were all excited! It was the best Christmas Eve gift Lisa could have asked for and Tom did an amazing job with it! And of course it happened at the top of a mountain!

photo

Lisa and Tom then began their search for a wedding venue where they quickly fell in love with “The Log Cabin” in MA. It’s a beautiful venue in the mountains and is dog friendly (because you know the dogs will be involved!), so they knew it was the one for them! They both love the fall so they booked 10/18/2025 and look forward to starting the next adventure of their lives together as a married couple!