Prince Harry's childhood friend Tom "Skippy" Inskip expressed reservations about Meghan Markle before the couple became engaged, it has been claimed.
According to the forthcoming biography of the Royal couple, Inskip - known to friends as Skippy - advised Harry and Meghan to live together before "doing anything more serious".
A source close to Duke and Duchess of Sussex told the authors of Finding Freedom, which is being published on Tuesday, that although his advice "came from a good place," Prince Harry "didn't totally see it that way".
The source, who is understood to have spoken to the authors with the permission of the Duke and Duchess, added: "It really hurt him that someone he was so close to would not trust his judgment."
It has been previously revealed that Harry's brother, Prince William, also advised him to slow down, leading to reports of a deep rift between the two.
Inskip and his wife Lara Hughes-Young were reportedly "punished" for expressing his reservations by being excluded from Prince Harry and Meghan's evening wedding party at Frogmore House in May 2018.
According to reports last year, Prince Harry and Inskip were reconciled after the death of his mother-in-law last year following severe mental health problems.
Inskip arranged the infamous 2012 Las Vegas party at which Prince Harry was caught playing naked billiards with showgirls in a hotel suite.
He was also with the Prince when he was seen inhaling "hippy crack" - or laughing gas - at another party.
It has also been claimed when Prince Harry and Meghan Markle first began their relationship, after a blind date in July 2016, Catherine, Duchess of Cambridge, had not "shown much interest" in the American actress.
A source told Omid Scobie and Carolyn Durand, the authors of Finding Freedom: Harry and Meghan and the Making of A Modern Royal: "Despite the fact that Harry was a regular guest in her household Kate seemingly didn't care to get to know who this woman was who had made her brother-in-law so happy."
However, this may simply have been a reflection of the fact the Duchess of Cambridge is an "extremely guarded person".
The source added: "Meghan was disappointed that she and Kate hadn't bonded over the unique position they shared" and that Catherine felt they did not have much in common "other than the fact that they lived at Kensington Palace".
Prince Harry and Meghan married at St George's Chapel at Windsor Castle on May 19, 2018 and went on to have a son, Archie, now 15 months.
The US celebrity magazine In Touch, which reported on Saturday the claims about Inskip's reservations regarding Meghan, has earlier claimed she has "no regrets" about her and Prince Harry's decision to move across the Atlantic in March this year.
"She looks and feels amazing," said a source, adding that the Duchess of Sussex is particularly pleased to no longer have to abide by the royal dress code.
"Meghan's gotten used to dressing down," a source said. "On a day-to-day basis, she wears jeans or yoga pants, big sweaters and flats or sneakers, which she feels comfortable and relaxed in, and keeps her makeup minimal," said the source.
Although the Duchess is said to enjoy getting "dolled up" from time to time, she "hated" the firm's "old-fashioned rules and regulations — like wearing dresses below the knee."