Devin Dawson Is Engaged to Leah Sykes — All the Details on His Romantic San Francisco Proposal

Devin Dawson is engaged!

The “All on Me” singer proposed to girlfriend Leah Sykes while on a trip to San Francisco to celebrate their two-year anniversary on Sunday, he confirms to PEOPLE exclusively.

Dawson, 30, popped the question privately on the rooftop bar at the new Virgin Hotel in downtown San Francisco, making it the first proposal to happen at the spot as the bar isn’t technically open yet. San Francisco is a city close to Dawson’s heart, and Sykes, 21, had never been before the trip.

“Sunday was the two year anniversary of our first date, and I’ve known for a while now that I wanted that to be the day I propose to her. I wanted to set that day in stone so we could always remember how important March 10th is to us,” the “Dark Horse” singer tells PEOPLE.

“I grew up around San Francisco and she’s never been, so we made a trip out of it and I got to show her around one of my favorite cities in the world. I think she might have suspected that I would pop the question this weekend when I took her to all my favorite spots —Ocean Beach, The Presidio, Twin Peaks — but I wanted to try to surprise her when she least expected it. So I waited until late Saturday night… When it turned midnight (our anniversary), our good friends at Virgin Hotels let me take over their rooftop bar.”

Sykes — who is also a singer-songwriter — was still unaware of the romantic surprise Dawson had up his sleeve, however.

“We went up for a ‘nightcap,’ but when the elevator opened our song was playing, there were candles everywhere and we had the rooftop to ourselves,” he tells PEOPLE. “I think it hit her then, because she just started bawling! I was really proud of actually catching her off guard. I got down on one knee and she screamed ‘YES’ to me with the entire city behind us.”

After proposing with a 1.75 carat round solitaire diamond, which he picked out and designed with a local jewelry maker, Dawson says the newly engaged pair “finished the moment off with her favorite rosé champagne, and I got to tell her about the ring and everything leading up to the best night of our lives.”

The “Asking for a Friend” singer adds, “I never thought I’d be the one to find the one, but it really is crazy how the right things will come into your life at the right time. Spending the rest of my life with Leah was a no-brainer for me, and we are both beyond excited and elated to continue our history forever. Cheers!”

On Friday, Dawson posted several photos and videos of himself and Sykes on their trip to his Instagram Story. The plane trip to San Francisco, as well as Sykes jokingly mistaking Alcatraz Island for the fictional “Harry Potter” prison Azkaban, was all documented.

Dawson and Sykes both attended Belmont University in Nashville and became acquainted through several chance encounters. In April 2018, they made their red carpet debut as a couple at the Academy of Country Music Awards.

At the time, Dawson told PEOPLE that it was “cool” to have Sykes by his side for the ACM Awards, where he was nominated as a new male artist. But later on in the evening, he said he caught the attention of Nicole Kidman after he was put on “shoe duty” and had to tote around Sykes’ uncomfortable heels.

“I look and it’s just Nicole Kidman sitting right there and she’s laughing,” Dawson said. “I’m like, ‘What’s so funny?’ And she says, ‘I just think it’s hilarious that you’re carrying her shoes. I think it’s the cutest thing in the world.’ So the first time I met Nicole Kidman I had my girl’s high heels in my hand…That’s ‘All on Me’ in real life right there: When you need me to hold your shoes for you, I got you.”

In January, Sykes posted a sweet birthday message dedicated to Dawson to her Instagram.

“Happy 30th birthday to my best friend,” she wrote in the caption, alongside a photo of Dawson with his arm around her. “Devin, you encourage me every day to reach higher in my work and in my personal life; to always exude truth.”

“You are loyal to your core,” she continued. “You are the voice I need to hear when I’m having my weekly mental breakdown. You know that when I’m venting I need a hype man and you’re a damn good hype man. You call me out. You listen to my crappy demos. You support me … You laugh at the innumerable memes I spam you with daily. You watch Vampire Diaries with me. You’re a crappy masseuse. You’re an amazing chef. You have this ability to make some of the weirdest faces I’ve ever seen. You’re a literal rockstar. You think of puns at an abnormal rate. Your fingernails are always so well groomed. You talk on the phone with my dad weekly. You respect me. You make me feel safe. You fold your socks kinda weird and you love me so well.”

She concluded: “My life has forever been changed because you were born. Today and every day we celebrate you. I love you Devin Dawson Durrett. As Taylor Swift once said, “[it’s] the end of a decade, but the start of an age.” Welcome to your thirties.”

Dawson released his debut album, Dark Horse, in January 2018 and first gained popularity after Taylor Swift shared a video of him and friend Louisa Wendorff performing a cover of “Blank Space” and “Style.”

“Taylor Swift saw it somehow and Tweeted it, Facebooked it and all this stuff — and it literally was the craziest viral thing I’ve ever seen,” Dawson previously told PEOPLE. “It’s unreal to me. She literally said one word. She said ‘Obsessed,’ and then posted the link to the video and it changed my life.”

Dawson — who has previously opened for Brett Eldredge, Tim McGraw and Faith Hill — recently wrapped his headlining “Stray Off Course” tour.

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