Meghan & Harry's Cringiest Valentine's Day Moments

The wedding of Meghan Markle, Duchess of Sussex, to Prince Harry, Duke of Sussex, was initially perceived as a real-life Cinderella story — American commoner marries royalty! (Swoon!) However, it hasn't been easy for this royal couple to reach a happily-ever-after. Harry and Meghan made an abrupt exit from the United Kingdom in search of privacy and peace of mind, only to find themselves subjected to almost as much scrutiny and criticism as they received as royals with The Firm. To add insult to injury, it's rumored that Harry and Meghan are having serious money troubles. None of their initiatives — not their Netflix projects, not Meghan's designer fruit jams — have found much success or acclaim.

At least the Sussexes have their fairy tale romance to brag about — well, kind of. While they may actually be the happy couple they present themselves as, when it comes to the most romantic day of the year, their Valentine's Day celebrations leave much to be desired. Let's look back at their most cringeworthy February 14ths.

Newlyweds have a lot of first holidays as spouses to look forward to after taking their vows. After Prince Harry and Meghan Markle's spectacular May 2018 wedding, one would have expected that they'd spend the following Valentine's Day enjoying some private time together. Instead, February 2019 found the newly minted Duke and Duchess of Sussex miles apart, since Harry went to Norway to address the troops who were stationed there. Meghan was left alone, which in itself was sad enough — but she also happened to be pregnant with their first child at the time. Talk about lonely hearts.

In 2020, Meghan Markle and Prince Harry, the Duke and Duchess of Sussex, were reported to be "all smiles" by TMZ when they were spotted in Canada on Valentine's Day after a jaunt to California. Under any other circumstances, royal watchers might have gushed, praising the young couple for planning a romantic getaway. However, this was no second honeymoon; the Sussexes had just announced their so-called "Megxit" from royal duties, and there was outrage aplenty over what the public saw as a betrayal of Queen Elizabeth and the entire British monarchy. Even now, resentment toward the Sussexes rages on.

For Valentine's Day 2021, the Sussexes announced that they were expecting their second child. The news was unquestionably joyful, since Meghan Markle, Duchess of Sussex, had suffered a heartbreaking miscarriage the previous summer. On the other hand, the couple's decision to share the news via a staged professional portrait on Instagram came off as performative. Controversy erupted yet again when the couple named their new daughter Lilibet. It was Queen Elizabeth's special childhood nickname, and critics accused them of disrespecting the beloved monarch.

What do you suppose the prince and the entrepreneur did to acknowledge their everlasting love in February 2023? Your guess is as good as ours: Meghan Markle, Duchess of Sussex, and Prince Harry, Duke of Sussex, avoided any public appearances and social media shout-outs on Valentine's Day that year. As it happens, Harry's revelatory memoir, "Spare," had been published a few weeks earlier. His soul-baring book not only failed to win him sympathy but also widened the gulf between him and his family. We can't say for sure that the backlash and the Valentine's silence are connected, but you never know.

Valentine's Day 2025 found the Sussexes spending the day apart: Harry in Vancouver for the Invictus Games, and Meghan at home with their children. She posted a message to "my Valentine" on Instagram on the 14th, including a black-and-white photo of the two of them exchanging a kiss in the middle of a meal. It's hard to tell which was more embarrassing: the staged smooch or the thought that Meghan likely created the post to avoid divorce rumors. Not to be outdone, Harry sprang for a pair of $3,600 diamond earrings to show his devotion.

Valentine's Day 2026 hadn't even arrived when Meghan Markle, Duchess of Sussex, made her most regrettable V-Day move yet. The week before, she promoted "a sweet surprise" from her boutique brand, As ever: the release of a limited-edition Valentine gift bundle featuring two of her fruit spreads and four gourmet chocolate bars.

Using the holiday for a product plug tainted any loving message Meghan might have been preparing for her husband. That's not even mentioning the price: $92 for the set, or $185 for a deluxe edition that includes a candle, a tin of hibiscus tea, and a packet of flower sprinkles. As a reporter for Sky News Australia commented (via YouTube), "You must love somebody a lot to give them one of those packages." We wonder if Prince Harry got one.