It has been roughly eight years since Ryan Gleason dropped to one knee on a snowy New Year’s Eve and asked Alexa Ray Joel to be his wife. Eight years. In the world of celebrity gossip, that’s an absolute eternity. Most couples have had two kids and a public divorce in that timeframe. But for Alexa, the daughter of music legend Billy Joel and supermodel Christie Brinkley, the long game seems to be the only game worth playing.
People are constantly asking: "When is the Alexa Ray Joel wedding actually happening?"
Honestly, the answer is a mix of bad timing, high standards, and a very New York sense of "we'll get to it when we get to it." There’s no drama here. No secret split. Just a couple that seems perfectly content to stay in the "fiancé" lane until the stars—and their hectic schedules—finally align.
The Proposal Heard 'Round the Hamptons
Let’s go back to the start. It was January 1, 2018. Ryan, a savvy restaurateur who owns East Village staples like Drexler’s and Boulton and Watt, pulled off the ultimate surprise during a family vacation. Alexa later admitted she was "dumbstruck." She’s a songwriter; she usually has words for everything. Not that day.
He told her, "Before I met you, my world was in black and white. You colored it in between the lines."
Cue the collective "aww" from the entire internet. He gave her a massive emerald-cut diamond with a vintage flair that felt very "Old Hollywood." It wasn't some cookie-cutter rock you see on every influencer's feed. It had personality. Just like her.
Why the delay?
You can’t talk about the Alexa Ray Joel wedding without mentioning the "C" word. No, not Christie. COVID.
By the time they really started digging into the logistics in 2019, the world shut down. Christie Brinkley herself confirmed to Extra back in 2020 that everything was on hold. Alexa and Ryan are "New Yorkers through and through," and they didn't want a "Zoom wedding" or a masked-up ceremony. They wanted the full, classic, Italian-dinner-party-at-Cipriani vibe. If you can't have the pasta and the dancing and the crowded piano bar, why bother?
What the Wedding Might Actually Look Like
Alexa has been pretty vocal about her vision over the years. This isn't going to be a "boho-chic" barn wedding with hay bales.
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- The Vibe: She’s called it "old-school Italian." Think dark wood, white tablecloths, and probably enough wine to float a boat.
- The Location: New York City. Period. She’s a city girl.
- The Dress: Expect something dramatic. She has a penchant for "va-va-voom" silhouettes—corsets, lace, and maybe a bit of a rock-and-roll edge.
- The Music: This is the big one. Can you imagine the pressure on the wedding band?
There’s a common misconception that Billy Joel will spend the whole night behind the keys. While he’ll definitely play—he’s the Piano Man, for crying out loud—Alexa has hinted that she wants her father to just be "Dad" for the night. She wants that father-daughter dance to be a moment, not a performance.
The "No Bridesmaids" Rule
One of the coolest details she’s shared is that she’s "over" the whole bridesmaid thing. No matching robes. No coordinating pastel dresses. She wants her friends there to enjoy themselves, not to act as props. It’s a refreshing take in an era of "Bridesmaid Proposals" and $5,000 bachelorette trips to Tulum.
The Billy and Christie Factor
It is rare to see an ex-couple as supportive as Billy Joel and Christie Brinkley. They are basically the gold standard for co-parenting. Just last year, in late 2025, Alexa got emotional watching the HBO documentary Billy Joel: And So It Goes. She called them the "ultimate dream couple," even if they didn't stay married.
Having both of them involved in the planning is a blessing, but also probably a lot of "too many cooks in the kitchen." Christie is a lifestyle guru. Billy is... well, Billy. They both adore Ryan, though. Christie has gone on record saying Ryan "just gets her" and looks at Alexa in that special way. That kind of parental stamp of approval makes the eventual Alexa Ray Joel wedding even more of a family victory.
Why the Wait Actually Matters
In 2026, we’re seeing a shift. People are tired of the "wedding for the Gram." Alexa and Ryan have been together for over a decade now. They’ve lived through a pandemic together. They’ve navigated the complexities of being a celebrity "child of" while building an independent career in soul and pop music.
Waiting hasn't weakened the relationship; it’s solidified it.
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When the Alexa Ray Joel wedding finally hits the news—and it will—it won't be a flash-in-the-pan celebrity event. It’ll be a celebration of a long-term partnership. It’ll be a New York moment.
Your Takeaway for Your Own Big Day
If you're stressed about your own timeline, take a page out of Alexa’s book.
- Prioritize the Vibe Over the Date: If you can't have the "Cipriani energy" you want, wait until you can.
- Parental Input is Great, But...: Make sure the groom is someone your family actually likes. Ryan Gleason being a "favorite" among the Joels and Brinkleys made the long engagement much easier.
- Ditch the Traditions That Don't Fit: If bridesmaids feel like a chore, don't have them. It's your party.
The world is still waiting for the official "Save the Date," but for Alexa Ray Joel and Ryan Gleason, the commitment has been there since that 2018 proposal. The party is just the icing on the cake.
Stay tuned to her Instagram—that’s where the real tea usually drops first. Whether it’s a surprise ceremony in the Hamptons or a black-tie gala in Manhattan, it’s going to be one for the books.
Next steps for you: If you're looking for ring inspiration similar to Alexa’s, look into "vintage emerald-cut diamonds with tapered baguettes." It’s a timeless style that avoids the "dated" look of many modern halo rings.