Join Alex in the studio for an interview with Winnie Harlow. Winnie spills all the tea about her romantic engagement, managing a long distance relationship, and why she loves couples therapy. The girls also discuss the hottest things to do with a partner and what red flag to always ignore. Enjoy!
Chapter 1: How did Winnie Harlow get engaged?
I'm sorry, but we have to get right into it. You just walked in here and I'm blinded by your hand. You just got engaged. Congratulations.
Thank you.
Tell me the story. I need to know like how he did it, how it happened. Tell me everything.
Chapter 2: What was Winnie's engagement story like?
It's so funny because I'm telling the story, but like I was the last one to know about it. Everyone like on my whole team was like, did you not realize that we've been voiding you for the past two weeks? I was like, I was none the wiser. Stop. It was so cute. Kyle told me that he wanted to go to Turks for Valentine's Day. And I was like, that is so cute.
It's like my favorite place other than Jamaica because I'm Jamaican. But we went. I got super sick. Classic. Classic. So romantic. I got super sick. And I feel like everyone was like super scared. Like, is this going to ruin the trip? Kyle was like, don't worry. Once this goes down, she will forget she's completely sick. And rightfully so. He was so right. This whole trip was incredible. I...
I got ready, I took a shower in the morning and he came into the bathroom and he was like, but you look good. I was like, thank you. Cause this is going to be a good trip. We're going to have a great time. He was like, yeah, we're going to have a great time. This is going to be a great trip. Oh my God.
When you – because I remember when I got engaged, I was similar to you where, like, everyone around me was, like, knew every detail to the point where, like, my husband flew my friends out and my family out. Like, everyone was there. Isn't that so beautiful? It's so beautiful to know that – I don't know.
I feel like when you become an adult, there's little moments where you actually feel like you get surprised in life and you actually are enjoying like people coming together and doing something special for you. Because when you're an adult, it's like you're getting the niece and nephews or your kids, the presents for the holiday. Like it's just not as magical in moments.
And when you have the people in your life come together to like make this fun moment that's so grand, you're like- I'm always a part, like I'm sure you are a part of like the planning of everything.
So it was like, I can't believe you guys pulled this off and not only pulled it off, but pulled it off as if I was a part of the planning. Everything was so perfect that I would have thought I was a part of.
You're like, I would have picked that. I would have picked that.
Everything.
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Chapter 3: What surprising actions did Kyle take for the engagement?
And so Kyle just got traded from the Wizards to Milwaukee. And we were joking, you know, he's like, I'm going off to work now, you know, I'll see you soon. I can't wait for you to come to Milwaukee. I was like, write me a love letter, my sergeant. send me a love letter. It was just a joke, you know, but he took that and wrote me a love letter to propose. It was the cutest ever.
I was like tearing up, crying, but crying just because it was so cute. I still had no idea.
So first you're like, he decks out this plane. You're on this gorgeous PJ. You're like, okay, my man is like really spoiling me. Then he's reading you a goddamn love letter. And you're like, I am so in love with you. Like already you're happy. You're ready to go. Exactly.
You're like, I'm good. This is going to be a great trip. Like, absolutely. This is going to be an amazing Valentine's Day.
But it's around Valentine's Day. So you're already just feeling like... It was the day before. Okay. So it's like romantic. You're feeling the vibes. And then... How does he pop the question?
So at the end of the poem, the way he wrote it, it was like as if he was going to say, will you be my Valentine? And it was, will you be my wife? And literally like just went into shock. I just I was already crying and just flooded with tears at that point. And he pulled out, hit the box, got out on one knee. And I was like, yes. I don't even need to see it. I don't need to see it. Yes, yes, yes.
Okay. First of all, that is so fucking cute. And were you guys alone or was your family around you?
We were alone. So apparently he wanted to do it in Turks with the family and everything. And just last minute, he changed his mind. It was like, guys, I'm doing it on the plane. And our moms were so mad. Like tell him he has to do it here. He has to be here. We need to see it. How could he? And he was like, y'all go enjoy the beach. Have a good old time. Y'all are in Turks and Caicos.
Have a great time. I'm doing it the way I want. And I love that he did that. It was so beautiful. So romantic. It was just him and I. And then surprise, everyone was in Turks. I had no clue as well.
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Chapter 4: How did Winnie and Kyle's relationship begin?
And I'm like, no, no, no. He's like, I promise they said yes. And like, I'm going through all this. So he's trying to calm me down. So in hindsight, I'm like, poor Matt is like, bitch, they're already fucking waiting for you. Like, just enjoy the moment alone with me.
100%.
And then let the family get involved.
It's so much pressure. I big them up.
incredible he did such a good job funny enough like even my nails my nail tech is actually from LA and I used to live here and I moved to DC with him and I've been like missing my nail tech because like I mean of course we love our nail ticks and he messaged me my nail tech to be like hey I have family in DC my cousin's birthday is tomorrow so I'm flying out there do you need your nails and like lashes done I was like
Oh, babe, guess what? Loy is coming out here. It's just a coincidence. Such an amazing coincidence. You know I've been missing him. And he was like, that's insane. Why is he out here? I was like, apparently he has family. I don't know.
And Kyle actually set the whole thing up. no okay that's actually i'm gonna hype your man up for a second yeah babe that is next level shit to be like i'm gonna think about my girl's nails to the point where i am going to fly out her nail tech the trusted person that does her nails so she feels so gorgeous okay okay kyle now you're just like making everyone look bad nuts Holy, that's so nice.
And then you look down and you're like... Okay, so I'm in the car on the way to the plane. And he was like, you were so annoying in the car. It was hilarious. I just kept looking. So he gave me this bracelet for Valentine's Day. So I'm like, none the wiser. Like I already got my Valentine's Day gift the day before. Like we're on our way to our trip.
And I'm like looking at my bracelet and my hands and my nails. And I'm like, babe, like the handpicks, like the beach, like it's going to be so nice. And his head, he's like... Yeah, it is. It's like, you don't even know.
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Chapter 5: What were the challenges of Winnie and Kyle's long-distance relationship?
what was that i was sick i was like i don't even know what he posted like was it cute like what right like this man that i don't really know like he just posted me on his fucking story and it's not like and it's not like this is not something that's gonna be seen by people you both have followings where it's like what is what was that right okay so i dm'd him and i was like hey that what was that and he was like oh i was just congratulating you on like your puma deal i was like
Oh, that's so sweet. Thank you. Appreciate it.
Sweet.
And obviously in the pandemic, we have nothing to do. So I was like, cool. Like, so what have you been up to in the pandemic? You know, whatever. Small talk. And we were... Messaging back and forth for a bit, but it was like I would message and then like five hours would pass and I wouldn't realize that he responded. And then I would see it. And it was just like three days of like small talk.
And I was like, hey, you know what? I'm not really super good at DMs. Like here's my number. Text me.
and yeah then we texted for like a few days and then he started facetiming me and he was like super sweet he would like have an interview to do you know like everybody was doing that whole like zoom interview stuff yes and he had an interview to do he was like hey i have like some work to do i'll call you back in an hour and i was like yeah okay cool like you're gonna call me back in an hour an hour literally called me back and i was like
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Chapter 6: How did Winnie and Alex's personal stories align?
A man of his word. We love this. We love this.
Wow. And so it just naturally progressed. That's like I, girl, we have like this. I were so in simpatico with this. I'm like, I met my man like literally online, on Zoom.
What did you meet him?
So we had like a random meeting that my agent was having me meet like with like TV and movie producers just to see if like I would ever want to do something in that space. And he was like my last Zoom of the day. And I always joke to him because I had these like men that were like fucking 60. Yeah.
right there's anything wrong with you yeah but they were like 16 I'm like in my hoodie I'm like looking not that cute and then the last zoom of the day he was late so I like googled him and I was like wait he's fucking young and hot what the hell I'm like putting my fucking lip liner I'm over lining my lips I'm pushing my tits up I get on the zoom I'm like hello and he was just so cute and charming but also like not overly like oh my god I want to be in business with the caller daddy girl so I kind of loved it that he wasn't giving me too much of the time of day and then we ended up talking and then I flew to LA and met him and when was this
This was in 2020. You lived in New York, right? Yeah. And Kyle lived in LA. Yeah. I lived in New York and Matt lived in LA and we met in the pandemic online. Oh my days. No, and then we- What is this synergy? No, it's weird. I'm telling you.
That's nuts.
That's why I was so excited to talk to you today because then seeing your engagement, I was like, girl, we have too much in common right now.
That's crazy.
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Chapter 7: What is Winnie's ideal night out?
Do you drink? Yeah. What's your go-to drink? Cocktail?
Yeah. I like mix something. If I'm just getting something on the menu, I love a lychee martini with extra lychees. I like a martini. I like an espresso martini.
I put it on my espresso martini. I'm like, it's so good. I like sweet drinks. Yeah, okay.
But I do like a dirty martini as well. Oddly, I love olives.
Okay, when you're drunk, are you the life of the party? Are you the person like Irish exiting or are you the drunk crier? Or like who are you in your friend group?
Um... I'm like life of the party and like talker. Like I love to communicate. It's like all the inhibitions are down. It's like, I love you so much. Like you don't understand. Like you're the baddest. Like period.
I feel like I'd run into you in a bathroom at a party in LA and we would be doing this, but like more annoying. Be like, no, no, but you don't know. You don't get it. But you're so gorgeous. No, that's so girl coded. You're just like, shut up. Shut up.
No, you shut up. But it's so fun.
That's literally Matt is always like, but what could you guys have been talking about? And I'm like, what do you mean? What do you mean? There's so much to discuss. Oh my God. You get it. Okay. You're one of the most famous supermodels in the world. So I want to play a quick game just to like catch your vibe. Let's do it.
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Chapter 8: Would Winnie do a modeling shoot with snakes?
As she looks down at her brain.
My man, my man, my man. You know. No. I feel like also everything is communication too. So like now if it was like a...
Dior campaign I don't have any control and whatever it's just like babe this is a situation whatever I feel like we're also very understanding too and that's a part of our careers you know like you may come across someone whatever as long as like we're aware you know yes you're not being like shady and not talking about it if it's like up front and it's gonna really help your career I agree for sure boom yeah get your nipples pierced for the shoot hmm I don't know I've I actually always wanted my nipples pierced okay but like
The pain. Like, I feel like those are one of the piercings that don't heal very quickly. I have so...
I love girls that do it, but I could never do that. I am such a little bitch with pain. I would be like, I would, I couldn't, I just could never.
I love the aesthetic though.
Oh my God. Like a little like white t-shirt and you see, I'm like, girl, you're crushing.
I love the aesthetic.
I couldn't, but I don't know.
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