The night we met…
It all began on a Friday night in February (17, 2023) at Nashville North. A place where you would typically find Derek on any given weekend. A place where he had grown his love for Swing Dancing and built a social outlet out of the norm for a introverted tech guy.
Little did he know this wouldn’t be a typical weekend. On this weekend, Gwen decided (forced cough cough haha) to celebrate her birthday with her Cousin, Bethany, and Co-worker/Friend, Bree.
Bree was determined to make it a great night to celebrate Gwen. She decided to find someone to dance with Gwen and show her a good time. Going to the bar, she noticed Derek waiting to get a drink and remembered him from previous nights out. Knowing he was a good dancer, she approached him and asked if he would come over and ask her friend to dance, pointing to the table where they were sitting. Trying to not be to forward and awkward, he let Bree know he would grab a drink and make his way over to the table soon, when the time felt right.
After a few songs and getting up the courage to go talk to a random girl, he head to the table. Once he got to the table, he realized this wasn’t just another drunk girl on her birthday. Gwen was actually really nice to talk to, things felt easy. Waiting until a great song came on, he then asked her to dance. They shared their first of many dances and had so much fun. After the song ended he dipped her, walked her back to the table and continued to get to know this girl that came out of the blue.
As the night got late (11:30 lol), it was time for Gwen to go home but Derek couldn’t let her leave without one last dance. At the end of the song, rolling the dice on making the right move, he dipped her and kissed her. To Gwen’s surprise, the kiss didn’t put her off, in fact it felt right.
After that, Derek couldn’t let her leave and just get her number…they made plans that night to go on a First Date the next evening.
First Date…
The next evening, Derek suggested Mexican food since that is a safe bet with any girl, they decided on Dos Amigos since it split the distance between their two houses. Gwen was super cautious meeting this random guy at a bar and didn’t want Derek to know where she lived (good job :)).
Derek was so nervous for this date because he knew it would be different, he had to make himself a drink before leaving the house and showed up 30 minutes early to make sure he didn’t get stuck behind a train and be late. (funny thing is even if he drove all the way around the train it would still be way less then 30 minutes haha)
Gwen trying to stay cool and not over think it, delayed getting ready until the last minute but still managed to show up on time. Having a pessimistic attitude around dating since she had been let down from guys in the dating pool and this was “just a random guy in a bar”, she still managed to get up the courage to say “Why not see what happens?”.
They enjoyed their meals and the conversations flowed smoothly with little to no awkwardness. They talked about their past and growing up. About Gwen’s boys and what they do for a living. About her dog Ember and his family in Orlando.
As they finished their meals, neither of them wanted to stop talking and spending time together. Gwen suggested they go do something fun, like pool. Derek knew of a pool hall, The Black Diamond, by one of his old apartments.
They met at the hall, got a few drinks and a table. They played for a few hours and continued to have amazing conversation. After they were done and the night was coming to an end, Derek walked Gwen to her car and kissed her good night.
Meeting the boys…
The next night, after Gwen put her boys down to sleep, she felt like she wanted to call Derek and continue the conversation. They talked until both of them had to go to sleep. This continued every night, because they both wanted to keep isolation from the boys, this was their way to continue to get to know each other and build a relationship.
They would go on dates when they could and occasionally Derek would sneak over to Gwen’s house after the boys were asleep and they would watch movies and spend time together.
After a few weeks of this, on March 5th 2023, Derek got up the courage to ask Gwen to officially be his Girlfriend. She accepted and they were both very happy.
They continued to date and get to know each other until Gwen felt comfortable and it was time for Derek to meet her boys. They scheduled a day at Roller Valley to go skating and meet in a fun environment. It went really well and Derek just fit in naturally into the family dynamic easily.
A few weeks later, on April 9th 2023, they decided to do Easter Sunday together. This included Church, Lunch and an Easter Egg Drop event (the order of events will be important to the story soon haha). Everything was going well all the way up through Lunch. We believe the boys got some bad deviled eggs and it didn’t sit well in their stomachs. By the time they realized something was wrong, everyone was already at the Egg Drop event and both boys need the restroom fast! Luckily, the event was held at a school where they opened the restrooms to the public so Derek took the boys and dealt with the situation. This was the point when Gwen realized Derek would be a good support person.
Three Little Words…
Fast forward to August of 2023. The relationship progressed naturally and they were falling for each other. One night, as they were laying in bed, Gwen had been feeling these feelings for a little while, she got up the courage to tell Derek “I Love You”. Even though Derek had also been feeling these feelings for a while, he wasn’t ready to say them back. Due to issues he had with saying it in the past, he wanted to be sure he meant it since this was such an important relationship.
After a few days of focus and reflection, he said it back to Gwen. She had been so understanding and supportive through this time, Derek knew this time was different.
Maui Engagement…
The relationship continued and in June 2024, Derek decided Gwen is who he wanted to spend the rest of his life with, purchasing an engagement ring. They were already plan a trip to Maui in September and that would be the perfect place to pop the question. Gwen almost messed it up when she questioned Derek the very next weekend on where the relationship was going long term. Derek’s response…”I have a plan, don’t ask questions or you will ruin the surprise.” haha. She trusted Derek and didn’t ask again.
Finally, after what felt like forever, summer was over and the family went to Maui. Derek didn’t know how he would pull off an engagement out of town with the boys. Luckily, Gwen had the idea to invite Derek’s parents to go along with to help with the kids and get to know everyone better. This setup the ability for them to go on a date night. Gwen also had the idea to go on a sunset dinner cruise for the date night since she really wanted to see a crater we couldn’t go to snorkel. This was perfect, Gwen basically planned her own engagement without knowing it.
The night came and they set out to sea. Even though Derek knew how he wanted to propose, he didn’t know exactly when would be the best time to do it. He decided to wait until after dinner was served because the sun hadn’t set enough at that point. Little did he know, as they were eating dinner, another couple was on the front of the boat and he got down on one knee first…this definitely put a damper on Derek’s plans but it ended up working out in the end because no one was focused on them, made things so much easier.
After dinner, Derek took Gwen to the front of the boat and asked her to dance. They danced to the sounds of the waves hitting the hull and the guitar player on the top deck. As for the how he wanted to propose…he wanted to recreate the first night they met when he dipped her and they shared their first kiss. As the end of the song came, he went to dip her and a wave crashed into the boat, causing him to lose balance and almost drop her…almost haha. He brushed it off and just continued to dance a little longer to re-setup the dip. He dipped her and popped the question. She immediately said Yes. He lifted her back to her feet, got down on one knee and presented the ring. Only one older lady saw what had happened, perfect for two people that don’t like the spotlight. (Sorry there aren’t any pictures of the proposal, that is a memory they want to share between the two of them.)
