Honestly, looking at the revolving door of celebrity flings, it’s kinda wild that we’re still talking about these two. But here we are. If you’re searching for the current winnie harlow boyfriend, you won’t find a "boyfriend" at all—because as of early 2026, he’s officially her fiancé.
NBA star Kyle Kuzma is the man who finally made the supermodel "hang up her jersey," as she once put it. They’ve been together since the world was basically shut down in 2020.
Most people think these high-profile romances are just for the 'gram or some tactical PR move. With Winnie and Kyle, it feels a bit more real. Maybe it’s the way they survived a brief split in 2021, or maybe it’s the fact that they’ve navigated his trade from the Lakers to the Wizards, and most recently, his stint with the Milwaukee Bucks.
That Insane Proposal (And the Ring)
Let’s get into the details because they’re actually pretty sweet. In February 2025, Kyle went full "main character" mode. He didn’t just pick a nice restaurant. He chartered a private jet to Turks and Caicos—a place they’ve loved since their first trip in 2022—and filled the cabin with roses and champagne.
He read her a poem. A whole poem.
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The kicker? He spent three months designing the ring himself. It’s an 8.5-carat oval-cut diamond that looks like it belongs in a museum. Winnie later told Vogue she was so overwhelmed she didn't even need to see the rock before saying yes.
When they landed, the surprises didn't stop. Their families were already at the villa waiting. It wasn't just a Hollywood moment; it was a family one.
The 2026 Wedding Watch
So, where are they now? Just a few days ago, on January 13, 2026, Kyle appeared on The Jennifer Hudson Show. He was playing it pretty close to the chest, calling their wedding plans "confidential."
He did mention they’re torn between a destination wedding and something local. Winnie, on the other hand, has been a bit more vocal about wanting an "island vibe." She wants heat, she wants dancing, and she wants a party that feels like her.
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Why It Works (The Fashion Connection)
One reason they’ve lasted is their shared obsession with style. Kyle isn't just a basketball player; he’s a fashion disrupter. Remember that oversized pink sweater that went viral? Yeah, that’s his energy.
Winnie has admitted that she’s his biggest critic and his biggest fan. She gives him pointers on his walk, and he encourages her to take risks. It’s a literal power couple dynamic where neither one is overshadowed by the other.
A Timeline of Their Chaos and Commitment
- The DM That Failed: Kyle actually messaged her back in 2019. She never saw it. Glitch or fate? Who knows.
- The Pandemic Pivot: He tried again in March 2020. This time, she replied. They spent a month on FaceTime for 24 hours a day before she spontaneously moved to LA.
- The Rough Patch: They actually broke up for a second in August 2021. By Christmas, they were spotted holding hands at Carbone in NYC.
- The Permanent Mark: Winnie got "Kyle" tattooed in cursive behind her ear in 2023. You don't do that for a "kinda-sorta" situation.
- The Engagement: February 13, 2025. The jet, the poem, the 8.5 carats.
What’s Next for the Couple?
If you’re following the winnie harlow boyfriend saga, the next big milestone is obviously the walk down the aisle. Kyle is currently busy with the NBA season—he just put up 18 points against the Spurs on January 15—but the "wedding coming soon" teaser on national TV suggests we won't be waiting until 2027.
If you want to keep up with them, keep an eye on:
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- Instagram: They still post their "hard launches" and high-fashion shoots there first.
- NBA Courtside: Winnie is a staple at Bucks games when her schedule allows.
- Wedding Registry Rumors: Keep a lookout for news on whether they choose a tropical island or a high-glam city wedding.
The transition from boyfriend to fiancé seems to have settled them. They aren't just the "it" couple anymore; they're becoming a fixture. It’s rare to see a pandemic-born romance survive the return to "real life," but these two seem to have figured out the rhythm.
Don't expect them to stay quiet for long. Between Winnie's Cay Skin brand and Kyle's basketball career, they are constantly moving. But for now, the "boyfriend" title is officially retired. Use fiancé. It’s more accurate.
Check Winnie's latest Instagram stories for glimpses of the wedding mood board she’s been hinting at during recent interviews.