Chilli may be preparing to walk down the aisle soon. The TLC singer has been dating actor Matthew Lawrence since 2022, and the two seem to be going strong. Chilli dished on her relationship with the Boy Meets World star during her visit to Fox 5’s talk show Portia. “This is the first time that we have both experienced being in a relationship to where, I mean—there's no drama at all. We get along, and we have differences but we, still to this day, we've never had an argument,” she said of their drama-free dynamic. “I don't even understand why we would have to have an argument in the first place.”
The “Waterfalls” singer also revealed that since dating her beau, she no longer has a fear of marriage. “I do not. I don't have any fear at all when it comes to him,” she said. “It is just the way he is as a man, you know? He is a good guy. He has an amazing heart, and I mean, he checks off all of my list except for a few I don't know yet—’til we get married.”
Chilli and Matthew's relationship may be taking another significant step in the future. In a 2023 interview with ET, Matthew shared their potential plans for children. "That's the game plan. That's what we're trying to do," he disclosed. This news is particularly exciting as Chilli already has a son named Tron with music producer Dallas Austin, and the prospect of expanding her family adds a new dimension to her relationship with Matthew.
While Chilli is known as a legend in music, her dating life often takes center stage. But that’s what happens when you’re linked to some powerful men. Here’s a look back at Chilli’s dating history.
Dallas Austin
The “No Scrubs” singer dated the super producer throughout the ‘90s, and he produced many songs for her group, such as “Creep” and “Ain’t 2 Proud 2 Beg.” The two welcomed their son in 1997 and shortly parted afterward. Their relationship was documented in the VH1 TLC documentaryCrazy, Sexy, Cool.
Usher
Usher and Chilli
Photo by Frazer Harrison/Getty Images
Usher and Chilli are probably each other’s most famous relationship. The former couple, which is still talked about to this day, were together from 2001-2004. They were still in touch over the years, but the “Unpretty” artist said she finally stopped all contact 15 years later.
Floyd Mayweather Jr.
Chilli and Floyd Mayweather Jr. sparked dating rumors after he appeared on her VH1 reality TV show What Chilli Wants in 2010. While the two looked really chummy on the show, the “Diggin On You” singer denied that they were ever romantically involved.
Nick Cannon
In 2016, Chilli and Nick Cannon were rumored to be dating. The Masked Singer host gushed about the mother of one in an interview with E! News. "She's amazing," he said about Chilli. "She's an outstanding person, but you gotta ask her what's going on." He later clarified that they were friends and he’d “be so lucky to be able to...be called dating someone like that."
Matthew Lawrence
Chilli and Matthew Lawrence have been together since 2022, and they sometimes give us glimpses into their relationship on social media. We can’t wait to see what the beautiful couple has in store for the future.
Let’s make things inbox official! Sign up for the xoNecole newsletter for daily love, wellness, career, and exclusive content delivered straight to your inbox.
Feature image by John Parra/Getty Images for Sandals Resorts
RELATED
What made it even more special? We were back in the place where we first fell in love, now creating new memories in the same sun-drenched paradise. From booze cruises, pickleball matches, and wellness shots, to alluring late-night jacuzzi rendezvous, soul karaoke, and far too much champagne mixed with tequila, to really good jerk chicken and repeat-visit-worthy Asian cuisine, bae and I had a time.
Couples Negril And Couples Swept Away: Twins On The West Coast Of Jamaica
And it’s fitting that we visited in June (which is considered low season—a time when there are less travelers and better deals) because these sister resorts are like Gemini twins that embody two distinct sides of the same spirit.
Set between Negril and Hanover, Couples Negril is the social butterfly, full of energy and artistic flair; Couples Swept Away is the introspective dreamer, grounded in nature, wellness, and tranquility.
While they’re quite opposite in vibe, they’re united by a shared history and reflect the classic Gemini duality: light and shadow, play and peace, expression and reflection.
Bae’s Favorite: Chic, Modern, And Cozy At Couples Negril
Couples Negril Suite
Courtesy, Couples Negril
Bae’s favorite was Couples Negril—which has more than 230 rooms and spans 18 acres—for its mix of entertainment, modern minimalist vibes, and a diverse crowd of couples. He especially loved Otaheite Restaurant with its low-lit red velvet love seats and dishes meshing luxury with traditional island flavors (like the merlot stewed rabbit served with coconut polenta and the filet mignon with the jerk glaze.) And he lives for hearing me sing, so the piano bar was our jam.
We also spent lots of time at the beach bar, one of five on the property, snacking on fish tacos and sipping margaritas just steps from our suite.
We saved the rum for the included catamaran cruise (book ahead!), which came with endless punch and views of Negril’s West End—a fave spot of ours. Couples Negril made the all-inclusive life feel surprisingly easy and fun.
The property also features a treehouse spa, two pools, four jacuzzis, an au naturale beach (whew, chile!), and sports facilities. Everything was easy to access—the layout felt cozy and well-organized, making it simple to move between activities and amenities. At this resort, you can really have some grown-and-sexy fun without it feeling like a raunchy spring break episode of Couples Gone Wild.
My Favorite: Private, Classic Charm, & Nature Mystique At Couples Swept Away
Couple's Swept Away Suite
Courtesy, Couples Swept Away
While I loved Couples, once we stepped over to Couples Swept Away, the lush nature set on 19 acres won me over. This twin, which has 312 suites, 7 restaurants, 8 bars, 3 pools, 5 jacuzzis, and a spa, leans into intimacy and seclusion, and I felt like we had more privacy and room to explore–just the two of us—at this property. The rooms are rustic-luxurious, dressed in island cedar, with classic shutters and expansive verandahs that have hammocks where you can enjoy bright flora, the sounds of exotic birds, and the sea views.
The absence of TVs—along with its tropical fantasy allure— meant a 10 out of 10 experience for me. This resort invites couples to breathe deeper, slow down, and truly get to the core of intimacy, all within the hum of nature.
There were hidden enclaves with dipping pools, jacuzzis, open-air cafés, and quiet corners where you can sit by ponds filled with fish and bird watch (or have a little sneaky link with bae!)
One of my favorite stand-out amenities at this resort: the 10-acre fitness complex just a short walk across the road from the main property where I’d have my early-morning me-time while bae slept in. It has 10 tennis courts, squash and racquetball courts, a fully equipped gym, and a wide range of wellness and fitness classes are held there. I also enjoyed turmeric and ginger shots at the wellness bar.
Other standouts for food and nightlife included Lemon Grass (where you can enjoy Asian-inspired food and listen to the live music coming from downstairs), the chic Patois Bar (which was the late-night hotspot overlooking one of the pools and serving your usual bar fare like burgers and quesadillas—felt like we were at a Miami nightclub), and the Aura Bar (where bae sang with a quintet of other slightly drunken men and where we did the cliche but super-lit millennial couple thing: danced the night away to Top 40 hip-hop, salsa, and rock classics).
The Patois Bar
Courtesy, Couples Swept Away
Baecation Tip: Just be sure your partner packs a few linen or dress pants, loafers or soft dress shoes, and a few button-down shirts for the restaurants that require reservations. Also book your table and all-inclusive excursions in advance (or on the first day you arrive at the resort).
All in all, this resort-hop wasn’t the stifling, prison-in-paradise all-inclusive experience I remembered from the Jamaica family vacations of my youth. It also wasn’t the stereotypical AI disaster of bland food, lackluster customer service, and senior citizen activities that many complain about on social nowadays.
Both resorts offered a fresh take on luxury, great food, and good vibes—all without losing the intimacy we craved. All-inclusives might not be our every trip vibe, but for this chapter? It was exactly what we needed, and we look forward to making repeat bookings at both Couples Negril and Couples Swept Away in the future.
Let’s make things inbox official! Sign up for the xoNecole newsletter for love, wellness, career, and exclusive content delivered straight to your inbox.
Featured image by Shutterstock