The 20 questions Meghan Markle should have asked Prince Harry, according to her best friend

In her new book, ‘Romances & Practicalities: A Love Story (Maybe Yours!) in 250 Questions,’ the Duchess of Sussex‘s best friend Lindsay Jill Roth details the hard-hitting questions every couple in a transatlantic romance should ask each other before going the distance.

Roth, a TV producer, has been friends with Meghan Markle since they attended college together at Northwestern University, and the duchess even served as maid of honor in Roth’s 2016 wedding.

While the author was inspired by her own relationship with now-husband Gavin Jordan, whom she affectionately nicknamed ‘the Brit’ in the book, Roth may have also taken inspiration from her pal Meghan’s transatlantic romance with the Duke of Sussex.

She paid tribute to her longtime friend in the Acknowledgements section of ‘Romances & Practicalities,’ describing her relationship with Meghan as ‘sisters by choice.’

‘Meghan Sussex, Meg, to be sisters by choice, still thinking the same thing at the same time after all these years – no matter how many miles between us – is my favorite part of our unbreakable bond,’ Roth writes. 

‘There for each other always, sharing a deep loyalty and understanding – I could tell you anything, and it would be okay. I carry your heart (I carry it in my heart).’

Throughout the book, Roth offers up 250 thought-provoking questions across twelve chapters, each one touching on important topics like finances, family dynamics, and raising children. 

Surprisingly, each question seems to touch on specific moments throughout her close friend’s life, from her budding relationship with Prince Harry, to her time spent as a senior working royal, to the couple’s subsequent departure from the royal family in 2020.

As such, FEMAIL rounded up the 20 questions that Meghan should have asked Harry, according to none other than the duchess’s best friend. 

How did your family resolve conflict? Do you approve or disapprove of that method? What would you change or not change to resolve conflicts in your future family? 

It’s no secret the British royal family has suffered its fair share of conflicts and tragedies, most notably following the death of the late Princess Diana.

In his bombshell memoir Spare, released in January 2023, Harry claimed his father, King Charles III, didn’t hug him after breaking the news that his mother had been in a car accident because he’s ‘not good at expressing his emotions.’

The incident wasn’t a far cry from Harry’s interaction with Charles following the release of his bombshell memoir, and his several interviews slamming the royal family’s treatment of his wife before the couple stepped down as senior working royals in 2020. 

Royal commentator Omid Scobie claimed in his book, Endgame, that Harry called his father Charles following the release of Spare, but their conversation was ‘awkward’ and the King was ‘cold and brief.’ 

Just over a year after Spare was released, Harry reportedly visited Charles for a ‘brief meeting’ in February 2024, following the revelation of his cancer diagnosis. Although Charles has been left wounded by his son’s behavior in recent years, he has always privately insisted he will keep the door open for him to at least speak.

It was reported at the time that Harry spent around 45 minutes chatting with his father, which is thought to be their first proper contact in 15 months. It was their first formal meeting in person since the late Queen Elizabeth II’s funeral in September 2022.

As for his estranged relationship with his older brother, the Prince of Wales, the two brothers have barely spoken to each other since he and Meghan left the UK for the US and abandoned royal duties, with their feud having been exacerbated by the publication of Spare.

The youngest brother also reached out to Prince William after his wife’s shock cancer diagnosis last year. Meghan and Harry were understood to have made contact with the Prince and Princess of Wales ‘privately,’ though little contact has been made since. 

When you’re upset or annoyed at someone, do you prefer to (1) remain silent, (2) say something as soon as those feelings arise, (3) wait a certain amount of time before raising the issue, or (4) do something else? If so, what?

Now made famous during Harry and Meghan’s sit-down interview with Oprah Winfrey in March 2021, the celebrated talk show host asked the duchess whether she was ‘silent or silenced’ during her time as a senior working royal.

‘The latter,’ Meghan dramatically replied.

If an issue arose between someone in your family and me, would you rather handle it with that person on my (or our) behalf or rather I handle it with them directly?

According to Harry’s revealing memoir, the duke wrote of many such cases in which he was forced to defend his wife to his own family. 

In one instance from the book, Harry wrote that his father instructed him not to bring Meghan to visit the dying Queen Elizabeth II at Balmoral in September 2022, citing ‘nonsensical and disrespectful’ reasons.

Enraged by his father’s perceived snub, Harry retorted: ‘Don’t ever speak about my wife that way!’ prompting the now-King to offer an apology.

However, when it came to Meghan’s feud with sister-in-law Kate Middleton, the California native was often left to fend for herself. 

Their earliest sign of discord came at the first Royal Foundation forum summit in 2018, as Harry detailed in his book how Meghan asked to borrow a lip-gloss from Kate.

He said that Kate was surprised, but rummaged around in her bag before offering it to Meghan.

Harry went on to claim that Meghan applied a little gloss to her finger, and rubbed it across her lips, before Kate made a ‘disgusted’ face.

Famously, the sisters-in-law had a disagreement over bridesmaids dresses for Harry and Meghan’s May 2018 wedding. In October that year, it was reported that a conflict over Princess Charlotte’s bridesmaid dress had left Kate in tears. 

Meghan later claimed during her interview with Winfrey it was the other way around, adding: ‘She [Kate] was upset about something, but she owned it, and she apologized. And she brought me flowers.’ 

In his memoir, Harry also recounts him and his wife being invited to have tea with William and Kate in July 2018 in a bid to clear the air after a series of disagreements. 

During their sit-down, Harry claimed Kate became upset and demanded an apology from Meghan for offending her when she mentioned her hormones after giving birth and suggesting it had affected her memory.

In the run-up to the Sussexes’ wedding, Harry wrote that Meghan told Kate that she must have ‘baby brain because of her hormones.’ 

Kate, who gave birth to her third child, Prince Louis, a month before Meghan and Harry’s wedding, was understandably upset by the accusation. But Meghan also became offended because she was reprimanded for her comments.

Harry said that Meghan was told she wasn’t close enough to Kate to make such remarks about her hormones, while Meghan said she spoke to all her friends that way.

William then called Meghan ‘rude’ to her face and ‘pointed a finger at her’ and explained: ‘These things are not done here’. In an excerpt, which lays bare the rift between the Sussexes and the Waleses, Meghan told William: ‘If you don’t mind, keep your finger out of my face’.

Defending his wife, Harry wrote: ‘Meg said that she had never intentionally done anything to offend Kate and that if she had, she begged her to let her know so she could avoid a reoccurrence.’

How do you feel about my siblings? How much time would you want to spend with them? 

Meghan notoriously claimed she grew up an only child at her home in California with her mother, Doria Ragland, despite having half-siblings through her estranged father, Thomas Markle. 

As for Harry’s large extended family, Meghan referred to the royals as ‘the big family I always wanted’ in a confessional scene from the couple’s Netflix docuseries, ‘Harry & Meghan,’ released in December 2022. 

‘When I look back at my own childhood. It was great. But I just remember feeling alone a lot,’ the duchess said in the fifth episode of their Netflix series. ‘I just wanted these cousins and these people. I just wanted all of that. And I didn’t have that big family.’

‘So when I was pregnant with Archie I was just so excited that we are going to be able to create for him that thing that I had always wanted. So I did just every thing I could to make them proud. And to really be a part of the family… and the bubble burst,’ Meghan said.

Upon meeting William and Kate for the first time, however, Meghan explained how her first interaction with her husband’s brother and sister-in-law was ‘jarring.’

The duchess revealed she was ‘barefoot’ and wearing ripped jeans when she first met the Walses. However, she did not know the ‘formality’ carries through behind closed doors and that she is a ‘hugger’ – which she did not realize was ‘jarring for some Brits.’

‘I started to understand that the formality on the outside carried through on the inside, that there is a forward facing way of being and then you close the door and think, “OK, we can relax now,”‘ she explained. ‘But that formality carries over on both sides and that was surprising to me.’

What if one of your family members disliked me? How would you handle that?

In Spare, Harry claimed his brother physically attacked him during an altercation at Nottingham Cottage over Meghan. 

Harry described what led up to the incident, claiming William branded Meghan ‘difficult,’ ‘rude,’ ‘abrasive’ and insisted he was trying to help his younger brother during a meeting about ‘the whole rolling catastrophe’ of their failing relationship and Harry’s rows with the press. 

The duke accused his brother of ‘parroting the press narrative’ about Meghan before a screaming match ensued, ending in a physical altercation. He said he gave the heir to the throne a glass of water and said: ‘Willy, I can’t speak to you when you’re like this.’

Describing what he claimed happened next, and insisting he was scared, Harry wrote: ‘He set down the water, called me another name, then came at me. It all happened so fast. So very fast. He grabbed me by the collar, ripping my necklace, and he knocked me to the floor. I landed on the dog’s bowl, which cracked under my back, the pieces cutting into me. I lay there for a moment, dazed, then got to my feet and told him to get out.’

Harry recalled the incident left him with visible injuries, including ‘scrapes and bruises,’ and said his wife ‘wasn’t that surprised, and wasn’t all that angry. She was terribly sad.’

How would you like to handle holiday family visits? Divvying up the holidays? Sharing holidays with extended family? Would you prefer to spend holidays alone? 

In 2017, newly engaged Meghan spent her first Christmas with the royal family, marking a significant step into royal life. Instead of staying at Sandringham, which had ample bedrooms, she and Harry accepted an invitation from William and Kate to stay at their newly renovated country residence, Anmer Hall. 

The decision to invite Meghan to her first Christmas at Sandringham five months before her wedding to Harry was seen as a highly personal gesture from Queen Elizabeth II.

‘It’s just like a big family like I always wanted,’ Meghan explained, reflecting on her first royal Christmas at Sandringham in their Netflix docuseries. ‘And there was just this constant movement and energy and fun.’ 

‘I remember so vividly the first Christmas at Sandringham,’ she recalled. ‘Calling my mom and she’s like, “How’s it going?” And I said, “Oh my gosh, it’s amazing.”‘

She then detailed how at dinner she was sat next to Prince Philip, ‘H’s grandfather.’

Meghan explained: ‘And I just thought it was so wonderful. And I was like, “Oh, we chatted and it was so great.” And I talked about this, and talked about this.

‘He [Harry] was like, “You had his bad ear. He couldn’t hear anything you were saying.'” I was like, “Oh, well, I thought it went really well.”‘

Christmas morning began with Meghan and Harry sharing breakfast with William and Kate at Anmer Hall, while Meghan later joined the royals for the customary walk to St. Mary Magdalene Church.

The event was much different from the couple’s recent ‘quiet Christmas in California,’ where Harry and Meghan now live after making their exit from the royal family nearly five years ago. 

The pair are believed to have missed out on an invite to the celebrations at Sandringham and stayed at their nine-bedroom mansion in Montecito instead. The duchess described the family’s ‘low-key’ approach to the festive period in America while speaking to Marie Claire last November.

‘We’re always making sure we have something to do,’ Meghan said. ‘Like any other family, you spend time having a great meal and then what do you do? Play games, all the same stuff, someone brings a guitar – fun.’

The former Suits actress also stressed the importance of making ‘room at your table for your friends who don’t have family’ such as feminist icon Gloria Steinem, who once joined the Sussexes’ Thanksgiving party.

Meghan added it’s important to the couple that their two children – Archie Harrison, five, and Lilibet ‘Lili’ Diana, three – experience the ‘magic’ of festive traditions such as putting out ‘carrots for the reindeer’ at Christmas.

Was the way in which your nuclear family was perceived by outsiders – friends, neighbors, coworkers, extended family – an accurate presumption? Did your family portray itself one way in public but function differently at home?   

According to Meghan, her public perception of the royal family was far different from when she actually met her husband’s relatives in person. 

In the third episode of ‘Harry & Meghan,’ she revealed that there was no formal instruction on how to follow royal protocol after meeting Harry. Instead, her knowledge of royal life was limited to what she had seen in ‘The Princess Diaries.’

‘Joining this family, I knew that there was a protocol for how things were done,’ Meghan said in the docuseries. ‘There’s no class and some person who goes, “Sit like this. Cross your legs like this. Use this fork. Don’t do this. Curtsy then. Wear this kind of hat.” It doesn’t happen. I needed to learn a lot.’

These days, it seems that it’s now Harry and Meghan who seem to be portraying themselves one way in public but differently at home. 

A recent Vanity Fair article shed light on the apparent disconnect between the couple’s public persona and their private lives, with Harry painted as a man ‘marooned beyond his nuclear family’ and lacking any meaningful friendships in the US. 

A source close to the couple revealed that Meghan herself has acknowledged her husband’s social struggles, admitting that Harry has yet to make any lasting connections since their move to California. 

‘Harry doesn’t know what real life really is,’ said one insider, explaining how the prince’s sheltered upbringing within the royal family has left him unprepared for life outside the royal bubble.

How often do you speak with your family? How often do you visit? 

Ever since Harry made several allegations against the royal family in his televised interview with Winfrey, a six-part Netflix docuseries, and a tell-all memoir, his communication with his father Charles is quite limited, while his interactions with his brother William are slim to none.

The 75-year-old monarch reportedly called his youngest son for his 40th birthday in September, as a source maintained there’s ‘still a lot of love’ between the father and son.

But there was ‘no call’ between William and Harry on the major milestone birthday as the brothers ‘don’t even speak,’ another source claimed.

However, ‘Harry & Meghan’ viewers did watch as Harry received a text from his older brother amid the fallout from their ‘truth bomb’ interview with Winfrey.

Harry was seen showing his wife his phone, before Meghan said: ‘Wow, H just got a text from his brother.’ 

He then put his arms above his head and said: ‘I wish I knew what to do.’ 

How often would your family like to visit you/us? Is that okay?

Despite Harry’s rift with the royal family, the one relative who has made the effort to visit the Duke and Duchess of Sussex at their new residence in California is his cousin, Princess Eugenie, and her husband, Jack Brooksbank.

Eugenie was the only member of the royal family to feature in personal photos shared in Harry and Meghan’s Netflix documentary in a testament to their closeness. 

One sweet snap from the second episode showed the pair out for a bike ride along a palm tree-lined stretch of pavement in California. The series also featured previously unseen photographs of the duke and his wife partying with Eugenie and Jack on Halloween.

Jack even enjoys a ‘bromance’ with Harry and while attending King Charles’s coronation in May 2023, Harry stayed close to his cousin’s husband.

Speaking of his friendship with Jack in his book, Harry said that he and Meghan were ‘deliriously happy’ when he and Eugenie got married – adding ‘and for ourselves, selfishly, since Jack was one of our favorite people.’

Would you ever live abroad if the opportunity presented itself? If so, where? 

Because the couple spent the early days of their relationship in Canada, where Meghan was still working on the legal drama series Suits, it made sense the Commonwealth nation would serve as Harry and Meghan’s temporary home after fleeing the UK in 2020.

However, it was only in due time that the Los Angeles native would return to California with Harry and her one-year-old son in tow.

The couple have since ’embraced’ their new life at their $14.65 million estate in Montecito, bringing up their children in the grounds complete with chicken coops, a vegetable garden and playground. 

‘Meghan does seem to run the household and make the decisions, but it’s not that he bends for her. It’s just a dynamic that works for them, and maybe one that he needs after everything he’s been through,’ a supposed friend of the couple told People.

What are your thoughts about mental health treatment for either one of us?  

Prince Harry has been a staunch advocate for mental health awareness, often sharing details about his many years in therapy. 

The duke previously explained how he started to see a therapist after ‘total chaos’ in his late 20s, before undergoing a further five year analysis after meeting Meghan. Since moving to the US, Harry has experimented with different styles of therapy, including EMDR therapy, which aims to help someone come to terms with trauma.

The couple could also be seen taking part in an emotional guided meditation exercise in an episode of their Netflix documentary.

How involved should grandparents be in our parenting? How often should they see the kids? What if they want to see them all the time? 

Following years of tension between his son and the rest of the royal family, Charles is believed to be dissatisfied with just seeing his grandchildren Archie and Lilibet on the occasional video call and hopes to be more present in their lives.

Sources previously claimed the King now wants to make up for lost time after meeting them just a handful of times, and feels the ‘lack of closeness with his California grandchildren acutely.’

Queen Camilla is also said to be encouraging his increased efforts, and he reportedly sent Lilibet a ‘heartfelt gift and card’ to celebrate her birthday in June last year.

How important is your career in terms of your identity? 

Before she became the Duchess of Sussex, Meghan worked and lived in Toronto filming the hit legal drama Suits for six years. In 2014, she also launched a much-loved lifestyle blog, ‘The Tig.’

The duchess is expected to return to her ‘domestic goddess’ roots, years after ‘The Tig’ shuttered in 2017, with her new lifestyle brand American Riviera Orchard. 

The luxury brand is expected to cover a wide range of home goods such as tabeleware, linen, jellies, jams, a variety of spreads and preserves, as well as stationery, yoga mats and blocks, and gardening gear.

Do you have any passion projects that you’re working on or want to create? If so, how would that work around your job? Our relationship? 

Harry, who served two tours of Afghanistan as a soldier, embarked on his own passion project in 2014 when he founded the Invictus Games, an international sporting event for wounded servicemen and women. In an emotional video ad released ahead of the 2025 games, the duke spoke about the ‘healing power of sport’ and its ability to ‘change lives and to save lives.’ 

‘For so many of these competitors, getting to the start line has been one of the hardest moments of their life,’ he said. ‘But at the Games, their lives are changed. Watching these magical moments happen, and sport being the facilitator of that, is very, very special for all of us to witness.’

Meghan made her first appearance at the Toronto Invictus Games in 2017 when she was 10 months into her relationship with Harry. Since then, she’s supported her husband at each subsequent games – including Sydney, Australia, the Hague, Netherlands, and Dusseldorf, Germany.

Meanwhile, the launch of Meghan’s American Riviera Orchard brand is expected to coincide with the premiere of her upcoming Netflix series, titled ‘With Love, Meghan.’

A description of the series read: ‘Produced by Meghan, ‘With Love, Meghan’ blends practical how-to’s and candid conversation with friends, new and old.

‘Meghan shares personal tips and tricks, embracing playfulness over perfection, and highlights how easy it can be to create beauty, even in the unexpected. She and her guests roll up their sleeves in the kitchen, the garden, and beyond, and invite you to do the same.’

The cookery show, which was scheduled to premiere on January 15, was delayed and moved to March 4 following the LA wildfire crisis.

How can we best support each other in our respective jobs or businesses?  

Shortly after stepping down as senior working royals and relocating to the states, Harry and Meghan co-founded their own venture – The Archewell Foundation. 

On its website, the non-profit organization says its mission is to ‘show up, do good,’ adding: ‘We meet the moment by showing up, taking action and using our unparalleled spotlight to uplift and unite communities – local and global – through acts of service and compassion.’

The foundation is separate from the couple’s Archewell media and business divisions, which have been involved in the couple’s multi-million-dollar deals with Netflix and Spotify.

What would you eliminate from your life if you suddenly had to live on a tighter budget?

As Harry and Meghan fled for Canada in 2020, just weeks after announcing their departure from the royal family, it soon became clear to the couple that they would also lose their taxpayer-funded security team.

Harry received full publicly funded protection before stepping back as a working royal and moving to Montecito with Meghan nearly five years ago.

‘The biggest concern was that while we were in Canada, in someone else’s house, and then I got told short notice that security was going to be removed,’ he told Winfrey in March 2021, explaining that the news came shortly before the world went into lockdown amid the coronavirus pandemic.

‘So suddenly it dawned on me, hang on a second, the borders could be closed, we’re going to have our security removed, who knows how long lockdown is going to be,’ he said.

‘The world knows where we are. It’s not safe. It’s not secure.’

At the time, it was estimated that security for the couple could cost upwards of $5.5 million a year – a sum that was previously paid by British taxpayers through the Metropolitan Police budget.

Many critics insisted that the couple should have to pick up the bill themselves after they quit working royal life in favor of a move to the US.

Still, Harry has continued to press ahead with his legal battle against the Home Office over his taxpayer-funded security. While the duke is not seeking a permanent return to the UK, the move to proceed with his three-year legal fight against the Home Office is believed to be an indication that he wants to spend more time there.

Do your parents pay any of your bills currently (including your cell phone bill)? If so, will they continue to do so in the future?

Harry said he was cut off financially from the royal family after he quit his senior duties and fled from the UK with Meghan and their then-infant son, Archie.

Speaking to Winfrey, Harry sensationally revealed his family ‘cut [him] off financially’ and said he was only able to step away from royal life thanks to money left to him by his late mother, Princess Diana.

‘I’ve got what my mom left me, and without that, we would not have been able to do this,’ he said.

Harry’s personal wealth before meeting Meghan was derived from the estimated £20 million ($25 million) inheritance from Diana. 

Prior to 2020, Harry also received money from his father’s estate, the Duchy of Cornwall estate. It paid the duke £2.3 million ($2.87 million) each year, a figure he and Meghan would later claim contributed to 95 percent of their office expenditure.

Would you accept financial help from your parents or elders if they offered it? 

While Harry and Meghan have remained financially independent since stepping down from the royal family, he reportedly received £8 million ($9.9 million) when he turned 40 years old last September, after the Queen Mother set aside cash for her great-grandchildren 30 years ago. 

A former Palace aide told the Times: ‘There was a trust fund set up at the time. It was a way in which the Queen Mother could set aside money for when her great-grandchildren were older and a way of passing a slice of her estate down in a tax-efficient way.’ 

What would happen if one or both of us lost our jobs? 

After quitting their royal duties, and subsequently being cut off financially from the royal family, Harry and Meghan were forced to make their own money – and fast. 

The duke and duchess told Winfrey during their primetime interview that they ‘had no plan’ to ink multi-million-dollar deals with the ‘streamers’ when they first quit the royal family.

‘During COVID, the suggestion by a friend was, ‘What about streamers?” Harry said, while Meghan added: ‘We genuinely hadn’t thought about it before.’

‘We hadn’t thought about it,’ Harry continued. ‘So, there were all sorts of different options. And look, from my perspective, all I needed was enough money to be able to pay for security to keep my family safe.’

In 2020, the Sussexes signed a five-year deal with Netflix that was estimated to be worth $100 million, which includes the couple’s ‘Harry & Meghan’ docuseries and her ‘With Love, Meghan’ lifestyle and cooking show.

Meghan will likely be able to use the upcoming show as a platform for promoting and boosting other ventures, such as her lifestyle brand American Riviera Orchard along with possible spin-off merchandise. 

The pair also signed a $20 million deal with Spotify, in partnership with their production company Archewell Audio. But the deal was ditched by the streaming platform after just one season of Meghan’s podcast, ‘Archetypes.’

In April last year, it was revealed that Harry had made £22 million ($27 million) from his book, Spare.

If we had to make an escape plan–if we had to abandon our homes and head somewhere safe–where would that be? 

Just weeks after announcing their departure from the royal family in January 2020, Harry and Meghan temporarily moved from their residence at Frogmore Cottage to a $14 million oceanfront mansion on Vancouver Island in Canada in a bid for privacy and financial independence. 

However, the couple – along with their one-year-old son Archie – soon made a beeline for California after Canada announced it would be restricting its borders due to COVID-19. 

Hollywood tycoon Tyler Perry – who had never met Meghan or Harry at that point – famously offered up his private jet for their so-called ‘freedom flight’ to relocate the couple from their home in Vancouver to his $18 million Beverly Hills mansion.

‘He was like, ‘My house is safe and I’ll make sure you have security. Take your time,” Meghan recalled in the Netflix docuseries. ‘I was like, ‘We only need to stay for a week, we can find somewhere to live.’

‘He was like, ‘You’re not just going to stay for a week, you’re going to stay for as long as you need and I’m going to get you there safely. And I’m gonna keep you there safely until you have somewhere to go.”

Tyler said about Harry and Meghan in the documentary: ‘They just wanted to be free. Be free to love and be happy. They did not have a plan. There was no plan.’