Being a celebrity might mean skipping the line at the hottest restaurant or snagging the latest beauty drop before it sells out, but as it turns out, no amount of fame or money can save you from the rollercoaster that is Valentine’s Day.
Whether you’re swiping through overpriced flower arrangements, dodging your mom’s “so are you seeing anyone” texts, or accidentally running into your ex at the one nice restaurant in town, Valentine’s Day is a universal mess.
And guess what? Celebrities are just as bad at it as the rest of us. We’re talking awkward dates, cringeworthy gifts, and moments so tragic they’d make a rom-com blush.
So, to make your Valentine’s weekend interesting, we did what any self-respecting gossip enthusiast would do and tapped our favorite magazine insiders to get the scoop on some of our favorite Black celebrities’ best and worst Valentine’s Day moments.
Read on, and you just might feel a whole lot better about your own love life. Or, at the very least, you’ll get a good laugh at theirs.
Related: 9 Black-Owned Sweet Treats To Buy Your Significant Others & Girlfriends This Valentine’s
Tamara Lawrance
For British actress Tamara Lawrance, one of her most unforgettable Valentine’s Day moments involved a grand romantic gesture—whisking her girlfriend away to Paris for a surprise concert.
“Surprising my girlfriend with a trip to Paris to see Ezra Collective was a Valentine’s highlight for me,” Lawrance told Ebony Magazine.
“It was a whole operation,” she continued. “I asked her to send me a copy of her passport the month before for some made-up reason, which was clearly innocuous because I’d forgotten it. She’s a big lover of jazz, and it just so happened that one of her favorite UK jazz bands was playing in the city of love, so I thought, why not?”
To keep the surprise intact, Lawrance played it cool, only telling her girlfriend to “pack some clothes that were NOT tracksuits (her default)” for what she made sound like a simple dinner and hotel stay—except it was in Paris.
“I’m so proud of how well I kept the secret because even when, much to her confusion, we got a cab to St Pancras on Valentine’s Day morning, she didn’t suspect a thing until we got to the Eurostar gates!” the Get Millie Black actress shared. “She was spun at how extra I am, but she loved it, and the pure joy and shock on her face was worth all the sleuthing.
The Paris getaway marked their first trip together and, according to Lawrance, set the tone for many more unforgettable adventures.
“That trip laid the foundation for many more amazing memories with her and set the tone for how much fun we always have traveling.”
Shaffer Chimere Smith
For singer-songwriter Ne-Yo, one Valentine’s Day stands out, but not for the reasons you might expect.
“I’ll go worst because everyone has a story about their best,” he shared with BET. “I was in high school and was actually broken up with on Valentine’s Day. I’m not going to say the girl’s name because I am not going to give her the satisfaction, but it was the way that she broke up with me.”
The R&B star recalled the moment with a mix of humor and lingering disbelief.
“She gave me a Valentine’s Day card, and I thought, ‘Oh, wow. How sweet of you!’ And inside the card, it said, ‘I think we should see other people.’ I looked at the card and then looked at her. She had this blank expression on her face. I asked, ‘Are you for real?’ and she simply said, ‘Yeah.’ That was a little rough!”
Maybe that’s why he’s all about the polyamorous life these days.
Jay Ellis
For the Insecure star, one of his worst Valentine’s Day memories was less of a romantic evening and more of a pre-breakup in the making.
“I wasn’t necessarily thinking about this day from the perspective of truly caring about her. It was just, ‘Oh, let me just grab this real quick to make her happy,’” the 43-year-old told Essence.
At that point, neither of them was happy in the relationship. They were just going through the motions, half-assing it, and doing things out of obligation.
“So, on this Valentine’s Day, we ended up having this mad explosive argument as we pulled up to the restaurant. Next thing you know, I’m dropping her off at her place, I’m back at mine. Then, three or four hours later, we’re on the phone like, ‘I’m sorry. I miss you. I love you. I didn’t mean it that way. I didn’t mean that.’”
Heather Headley
For Sweet Magnolias actress Heather Headley, every day feels like Valentine’s Day at her house, so picking one memory wasn’t easy.
“The truth is, every day is Valentine’s Day at my house, so it was a little difficult to pick one memory. I know that sounds a little corny, but it’s true,” she told Ebony Magazine.
But one particular Valentine’s Day stands out for her and her husband. They had booked a reservation at a fancy restaurant, both dressed to the nines and ready for a romantic evening. But life had other plans.
“As we got ready to leave, things started happening around the house… The kids needed our attention, phone calls were coming in, someone needed this, another needed that – and suddenly, we were late and knew we couldn’t make it to the restaurant on time,” she recalled.
With no luck getting into any nearby restaurants, the couple finally stumbled upon a tiny taco joint.
“I was all dressed up in my heels, and we walked up to the counter, ordered a bunch of food, took our food on the little trays, sat down with our Styrofoam cups and fountain drinks, and had the best time,” she said.
What could’ve been a frustrating evening turned into a perfect one.
“We ended up just doing what I love doing with him the most: hanging out with him, talking to him, and giggling with him—I guess pretending that we were back in college. It was a perfect Valentine’s.”
Tristan Mack Wilds
Mack Wilds knows heartbreak all too well when it comes to Valentine’s Day. The actor went all out—buying what felt like a thousand roses and a giant teddy bear—only to get dumped.
“And I just spent the whole day tearing the rose apart petal by petal,” he recalled.
I guess it’s not just us ladies who have those dramatic breakup moments.
Sherri Shepherd
For comedian and talk show host Sherri Shepherd, one Valentine’s Day was less about romance and more about revenge (almost).
“I was going out on a date one Valentine’s Day. I was out in L.A. from New York, and we were supposed to go golfing. I got stood up. I had rented golf clubs and everything,” Shepherd told BET.
Heartbroken and furious, she did what any scorned woman with good friends would do—she called Niecy Nash.
“I called up my girlfriend Niecy Nash, she was over at Reno 911! and told her to come because I was about to tear up his car and wanted her to go with me—she’s my aiding and abetting girlfriend,” Shepherd recalled.
The two drove over to the guy’s place, ready for some well-earned destruction. But there was one problem. Mans lived in a gated community.
“The only reason I couldn’t throw a rock through his window was he lived in a gated community. That was my worst Valentine’s Day.”
