All The Juicy Details About Prince Harry & Meghan's First Dates

If you were genuinely surprised by the announcement of Prince Harry and Meghan Markle's status of boyfriend and girlfriend, you weren't alone. The notorious bachelor prince had a few high-profile relationships throughout his 20s and it certainly seemed as though his romantic escapades couldn't avoid the headlines. Meghan, meanwhile, was not just on a different page but in an entirely different book — she had been married, established her career as an actor, and went to Northwestern University — simply put, these two could not be more different. But, despite navigating two completely different worlds, they somehow collided. When their relationship went public, it certainly seemed as though Harry — who so many of us watched grow up, make mistakes, and watch as his brother got married and had kids — finally got the love he deserved.

In the blink of an eye, Harry and Meghan were engaged and their relationship seemed to mark a new era for the royal family. The "Suits" star couldn't have been further from the royal mold — American, mixed race, divorced, and a career woman. But she certainly could've stood for the modern monarchy that King Charles III and the likes of him have expressed interest in. Of course, the realities for the couple were far from the royal fairytale and they soon left their positions for a much calmer, boundary-ruled life in California, taking back control of the narrative and sharing their stories — including what their first dates were really like.

Harry was in awe of Meghan's beauty before they even met

If you've ever thought that your favorite celebrities are lurking on social media through private accounts, the answer is yes — they definitely are. Prince Harry was no exception, and his private Instagram account allowed him to engage with the social media world without the pressures of maintaining an official page. In many ways, it allowed him to simply connect with others. With that said, it was through the said profile that Harry first got a glimpse of Meghan Markle, who just so happened to pop up on his feed on the account of a mutual friend.

Remember the Snapchat filters we all used to be obsessed with and would actually post to our main social media pages? Well, Meghan and her friend, Violet Von Westenholz, used the dog ears and nose filter to film a funny video and it ended up on Harry's feed. He was smitten.

"I was scrolling through my feed and someone who was a friend had this video of the two of them, like a Snapchat," he said during the Netflix documentary, "Harry & Meghan." "That's what he saw of me," Meghan said, to which he responded, "That was the first thing. I was like, 'Who is that?'" completely taken aback by how beautiful she was, even with doggy ears!

Meghan slid into Harry's DMs with just three words

Violet Von Westenholz should really get credit for being the ultimate wing woman because she went on to pass Prince Harry's Instagram account details to Meghan Markle. Of course, the account was private and used a pseudonym, so Harry had to allow the gorgeous "Suits" star to follow him — not a problem, given that he already had heart eyes for her. Like any good single woman, Meghan then scrolled through Harry's account to get a sense of what kind of photos he posted, what his social media use was like — you know, all the detective-like habits we all do when feeling someone out for the first time. If she was expecting clues into his royal life, however, Meghan may have been disappointed.

As it turned out, Harry's Instagram was mostly full of pictures he had taken during different trips to Africa, an incredibly important continent for him where he had spent years living and working in different countries. Focusing his work in part on conservation efforts in Botswana, Harry's feed pictured endangered species, incredible views, and the natural splendors that only Africa can boast. Meghan, meanwhile, took the opportunity to comment and slid into the prince's DMs, as she detailed in their documentary. "Hello! Beautiful photos," she wrote to him. Of course, the rest is history.

The actor was adamant about having a 'single girl' summer that year

Many of us know what it's like to want a hot girl summer — relationship status regardless. As for Meghan Markle, her life was pretty much set and she was determined to have a season of life fully dedicated to herself. On the career front, "Suits" was at the height of its success and she had a great job on set, not to mention the humanitarian work that she was already dedicated to. Personally, her divorce from her first husband Trevor Engelson was well and truly behind her (they got divorced in 2014), so she was ready to live life on her terms. In fact, she spoke about her determination to only follow her rules during the couple's Netflix documentary.

"I was really, like, intent on being single and just [having] fun girl-time," Meghan said of the summer of 2016. Like any good highlight reel, the documentary went on to show footage of Meghan and her friends traveling, enjoying life, taking a break from work, and jet-setting across the globe in pursuit of the perfect summer season. "I had a career, I had my life, I had my path," Meghan continued, "And then came H. I mean, he literally — talk about a plot twist."

Harry and Meghan started texting on a 'surreal' day for the prince

Like any meeting through social media, Prince Harry and Meghan Markle started chatting back and forth in their DMs (again, all thanks to Violet Von Westenholz, what a homegirl). From there, the two exchanged phone numbers and started chatting via text, and as detailed by Harry in his memoir, "Spare," he and Meghan had what can only be described as an endurance race of a conversation. Going on for hours, the two got to know one another on a deeper level, and it was only after the fact that Harry realized just how cosmic their interaction was — and specifically when it took place.

"It occurred to me how uncanny, how surreal, how bizarre, that this marathon conversation should have begun on July 1, 2016. My mother's 55th birthday," Harry wrote in "Spare," noting just how fated his and Meghan's interaction really was. Whether you love them or hate them, that fact in and of itself is a little chilling.

As it turns out, that's not the only Diana-connected date that has popped up for the couple. When they announced Meghan's pregnancy with Lilibet, they chose to do so on Valentine's Day 2021. Amazingly, Diana had chosen the same day in 1984 to announce her pregnancy with Harry, and the prince had no idea. "I was shocked. We had no idea. It was just a coincidence, or maybe not a coincidence," Harry said in the couple's Netflix documentary.

Meghan maintains that she never Googled Harry before they met

Raise your hand if you've ever Googled yourself. Now raise the other if you've ever Googled the person you're talking to on Hinge — if your hand isn't straight up in the air, we know you're lying. A cursory Google search seems customary, especially in the era of app dating, and Prince Harry has quite the history when you run an internet search on him. Though we know him as an adult and for his more recent media appearances, Harry has existed in the public eye since the moment he was born — seriously, the media flooded the streets outside the hospital when Princess Diana gave birth to him. From that moment on, everything — the good, the bad, the ugly — of Harry's life has been documented and is fully available for the world to see at any time. It was shocking, then, to learn that in their early conversational period, Meghan Markle never once Googled Harry — an aspect of their relationship she maintains to this day.

"So that's the thing. When people say, 'Did you Google him?' No. But [the feed] is your homework," she said in the couple's Netflix documentary. "You're like, 'Hmm, let me see what they're about in their feed, not what someone else says about them but what they are putting out about themselves." Calling Harry's photographs the "best barometer" to get to know him, Meghan was certainly taken with what she saw.

The couple decided to meet for the first time, but almost hit a roadblock

So, through Instagram DMs and texting, Prince Harry and Meghan Markle got to know each other — at least enough to meet up. Like any good love story, they decided to go on their first date. Of course, being a prince and one of the most watched royals in the world, options were limited for Harry. "She didn't realize that being royal meant being radioactive, that I was unable to just meet at a coffee shop or pub," Harry said in their Netflix documentary, but Meghan wasn't deterred. She suggested the Soho House at 76 Dean Street, "her headquarters whenever she came to London," as they had a private social club that would allow their first date to happen without the prying eyes of paparazzi.

Meghan didn't travel all the way to London to meet Harry — she was already in town to attend Wimbledon, and she carved out some space in her schedule to meet the prince. In a hilarious turn of events, however, the "Suits" star almost didn't give him a chance.

"You were late!" Meghan said of their first date. "And I couldn't understand why he would be late. [I did not want to date] one of those guys who have so much of an ego that any girl would sit waiting for a half hour for you." Harry, meanwhile, was stuck in traffic and was panicking on his way to meet Meghan.

Harry detailed his first impression of Meghan in his memoir

Though he was red-faced and freaking out on his way to meet Meghan Markle for the first time, Prince Harry slowed down just enough to notice her as he walked into the Soho House. Though they spoke about meeting at his place initially to avoid the public, they ultimately decided that the social club was ideal — Meghan was sitting on a sofa when Harry walked up, and he noticed every little detail that he would later include in his memoir, "Spare."

"She was wearing a black sweater, jeans, heels. I knew nothing about clothes, but I knew she was chic. Then again, she could make anything look chic," Harry wrote in his book, noting that while he had seen photos of her from "Suits" and glam shots of her on the red carpet, she was even more striking in person. "Here she was, in the flesh, no frills, no filter... and even more beautiful. Heart-attack beautiful," he wrote. "I was trying to process this, struggling to understand what was happening to my circulatory and nervous systems, and as a result my brain couldn't handle any more data."

If they don't talk about you like that, ladies, don't date them!

Meghan left their first date after an hour but asked the prince a serious question

One of the biggest tricks of the dating trade is to leave them wanting more, and Meghan Markle's first date with Prince Harry is a perfect case study. For so many of us, we would've done just about anything to land a date with one of the world's most eligible bachelors, but not Meghan — her standards were high that night, and their date was cut short not only by Harry being late but by her leaving after an hour. Telling him that she had other plans, Meghan got up and left, certainly leaving Harry wanting to get to know her even more. Honestly, we love her even more for this unapologetic move.

Speaking of her decision to leave after an hour, Meghan said in the couple's Netflix documentary that it was only a couple of hours until she picked up the phone to contact Harry once again. This time, she had an important question.

"I called him that evening and I was like, 'Look, I'm leaving the day after tomorrow. Do you wanna grab dinner tomorrow night?' And I'm sure he thought it was so forward and American. I'm sure he told me it was so forward and American," she said. "We went and had dinner the next night at the same place."

In a hilarious turn of events, Meghan was late to their second date

By some twist of fate, Prince Harry and Meghan Markle had found themselves back at the Soho House for dinner the following night — the universe has an amazing sense of humor, because Meghan was late for dinner that night, following in Harry's footsteps from the date prior. Granted, however, Meghan clarified during their Netflix documentary that she was only late by a couple of minutes — "But you were quite flustered," Harry poked at her during their interview.

"I hate being late," Meghan explained. "Well, I had come back from Wimbledon and, you know, when you get all dolled up I wanted to go home and take a shower and then run over looking more like myself," to which Harry recounted, "I was like, 'You can be as late as you want. I ain't moving. I wanna see you again.'"

After Meghan arrived, the night went off without a hitch. The two were clearly smitten with one another, and to memorialize the night, they posed for a selfie — Harry's arm around Meghan smiling at the camera, while she laughed into the crease of his shoulder. "There was one photo. We just wanted to capture the feeling of just sitting in that little restaurant and going, 'Oh my gosh. I think we're going to give it a go,'" Meghan said.

FaceTime became an integral part of their long-distance relationship

And just like that, Meghan Markle had to head back to Canada after attending Wimbledon — Canada is where she was living and shooting "Suits" at the time. She and Prince Harry's whirlwind of a romance was all of the sudden separated by an ocean and a couple of time zones, so like any modern couple, they relied on texting and FaceTime to keep things going. Speaking of those early days chatting and getting to know each other even more, Meghan said in their Netflix documentary that the privacy they enjoyed allowed their relationship to blossom naturally, a luxury that Harry hadn't always been afforded.

"At the beginning, our relationship was this guarded treasure. It was long-distance from the beginning. Everything was just texts or FaceTimes and we'd talk for hours. And it just felt exciting, which was so weird because it wasn't exciting in the way I think people would assume it would be. It was just relaxed and easy," Meghan explained. "We just got to know each other, truly, like any other couple. You're figuring out what do you like to eat, what do you like to cook, what kind of movies do you like?"

For his part, Harry knew Meghan was special. "I was like, 'Now I'm really falling in love with this girl.' So despite my own fear, I just opened my heart to see what's going to happen," Harry said.

Their third date was a bit out of the ordinary

So when it comes to the first couple of dates, it typically goes coffee, then drinks, then dinner. For Prince Harry and Meghan Markle, they did drinks, dinner, then Botswana. Yep, their third date consisted of a trip to the country that held an incredibly special place for Harry and it was there that they took their relationship to the next level.

"I'm getting on the plane, and I'm going to the middle of the bush. What? What am I doing?" Meghan said of the wild invitation Harry extended to her for their third date. "Like, what if we don't like each other and then we're stuck in the middle of the bush in a tent? So I get there, this is the first time I've seen him in a month," she carried on. "We were very awkward at first. Like, 'Oh God. Do we kiss? Do we ...?' And I just remember he handed me a chicken sandwich."

As for the trip itself, it was full of memory-making moments and one particular scare, which Harry detailed in his memoir. Hearing a lion roar just outside their tent, Meghan shot up with a sense of fear, to which Harry responded, "Trust me, I'll keep you safe."

The Botswana trip prepared them for the media attention after their relationship hit the headlines

They say that navigating love can be like trekking through the jungle, and Prince Harry and Meghan Markle's relationship has been akin to being on the world's longest and most treacherous safari. Shortly thereafter, their romance hit the headlines, and all of a sudden, the world's paparazzi and media were paying attention to the couple and every little detail. Recounting what it was like to suddenly be projected into this newfound sense of international fame, Meghan recalled that her and Harry's trip to Botswana was actually the best kind of training they could've had for navigating the treacherous waters together.

"The next morning [when news of our relationship broke], it was so overwhelming," Meghan said during the couple's Netflix documentary, thinking back to their third date and the way in which they trusted each other in such an unpredictable terrain. "I said, 'Okay, well then, I'll just treat it like we're in the bush. Because like, it's all foreign to me, but I trust that you'll keep me safe, and you'll get me through it," she said.

Of course, the couple has since survived a litany of challenges, and are now in charge of their own narrative. To say that those first dates were a whirlwind is certainly an understatement.