We're going on some of the most expensive dates in the world. Like this $500,000 date that includes the entirety of Disneyland, all for ourselves… a $100,000 date at this mega complex with a massive waterpark and indoor ski resort… a $50,000 private island date… Best date ever! a $10,000 date cooked by Gordon Ramsay… and we even convinced superstar singer Madison Beer to go on a date with my most awkward friend.
All starting with this $1 date: a Ferris Wheel! - Here's $1. - Ok.
- Ladies first. - Thank you. Take notes, men.
Is this safe? I see why it's only $1. The $1 date has now begun.
It's, uh, making a lot of noise. Why is it making that noise? It's just the wind, right?
I usually film 20, 25 days a month, and I don't really get to spend much time with my fiancee, so I literally picked this video so me and my fiancee could spend more time together. I love you, even if you didn't take me to Disneyland. Well… not yet.
But for the final date in this video, for the first time in history, Disney reserved the whole park just for us. That's it for the $1 date! Let's head out to the $10,000 dinner date— After you, babe.
Turn off the park. I'll see you guys there. And now, the $10,000 date where we're gonna be recreating our first-ever date with sushi.
- After you. - Thank you. She doesn't know this, but Gordon Ramsay's gonna be making us the meal for this date.
Thank you. There you go. You look really cute.
I picked this just for you. It's been a long time since my first date with Thea, and now that we're engaged, I'm really excited to explore the world's most expensive dates with my fiancee. You're probably wondering, "Why is this the $10,000 date?
" Why is it? Gordon Ramsay himself is gonna be cooking our meals. The Gordon Ramsay?
Yep. Come on in. Welcome to Lucky Cat Miami!
It's nice meeting you! How's it going? What an amazing night this is gonna be.
Oh, I'm excited. Yes. We're gonna kick off with some pea guacamole with some delicious crackers.
Did you say peacock? I said pea guac! Oh, pea guac, oh… Not peacock, babe.
To celebrate this $10,000 dinner, some seriously exclusive sushi. Ladies first. Cheers.
Yeah, this is good. We have a delicious gourmet fried chicken, wonderful fried rice, and duck bao buns. Duck tacos?
Bao buns! Duck tacos. Bao buns!
You can yell at me. I will do in a minute. You're pushin' my limits, man.
Enjoy. I want you to take the first bite. I knew you were gonna do that.
It's only the $10,000 date, and we already have the world's best chef cooking a romantic dinner for the 2 of us. Nothing could possibly ruin this moment. Chef.
What are you guys doin' here? No, no no, no. - I got you.
- Come on, man! Don't rip it! I'm not ripping it, chef!
I'm not ripping it! Oh my goodness, mate. Why are you disrespecting his restaurant?
This is supposed to be a romantic dinner! Nolan, mine's burning. That's it.
I'm done! What are you? An idiot sandwich!
That is worth 10K alone. You guys have turned it to a nightmare! For $10,000, Gordon had a romantic surprise for our final course.
This is nice! This is romantic! This is actually very romantic.
Aww. Thank you. This 10K date was amazing.
I can't imagine how insane these dates are gonna get later in the video. The $50,000 date is this entire private island, so me and Thea brought some friends with us to make this a quadruple date. Wait, what?
What is that? This is Tom, the turkey. Please tell me we're not eating Tom.
We are not eating Tom. I didn't know if this was like a Say-Hi-To-Your-Dinner thing as you arrive. We have this entire $50,000 island and everything on it to ourselves.
I say the best way to kick off an island date is to go jet skiing! Let's go! Best date ever!
You might recognize Grizz and Hase from the video where they spent 74 days in the wilderness together. The day I took that hood off and saw you was the best day of my life! And you saw these two when Josh spent 22 days in solitary confinement.
These three spent weeks away from their wives, so I thought I'd give them some quality time together. This is the best date we've ever been on! Does the wife approve?
I approve! This is how I make good with all the people I put in prolonged places. Oh my gosh, that was so close!
Hey, Jimmy! It’s Nolan! Yo!
Uh-oh, we're bouncin'. Nolan is flying solo for this date, but later on, he'll be going on a date with Madison Beer. I, uh— the great outfit… Everyone, the island is all yours.
Go do whatever you want! So we all enjoyed the luxuries of this $50,000 island date. All right everyone, heads up!
Like hitting golf balls that are also fish food right into the ocean. - Thea, you show me how it’s done. - I actually don't know how to do this.
Now we're getting couples' massages on the beach. There is just a person on my back. Very relaxing.
Grizz and Hase were playing some beach volleyball… against their wives, of course. And Josh and Kenna were having a picnic on the beach. I forgive you for taking him away from me for so long.
- Welcome in, guys. - Oh wait, there's rose petals. I mean, I laid those just for you.
For 50 grand, we all get these luxurious bungalows. Where do the petals lead? I mean, look where the petals lead.
Into the lovely master suite. I made a heart just for you. It is so pretty.
And you picked them yourself? - Oh, I made this myself. - Wow.
And as the sun was setting on this $50,000 date… To our loved one! Cheers! …Nolan was the only one at dinner without a date.
Until Tom the turkey showed up. Nolan, we found you a partner! Uh, I'm all good on Tom.
And after dinner, we did some couples dancing. Rate our dance move. Again.
Got it? Come on! And after dark, we had a beach campfire, and I had a surprise for everyone.
Cue the fireworks show! And lightning at the same time! - Nolan, your date showed up!
- Tom the Turkey! Yo, why are you standin' so still? That's it for the $50,000 date!
I'll see you guys at the next one. For double the cost of the previous date, we get this massive indoor metropolis all to ourselves. There's a giant theme park, the largest indoor water park in America, even its own weather control system so they can have the largest indoor ski slope in America.
Ooh, it's so cool. This is terrifying! And while Thea loves skiing… I haven't told her… I have no idea how to ski.
Babe, this is massive! You're scared? Don’t be scared.
I'm not scared. Nah. You're good.
Hey, what's over there? - What? - I'm freakin' terrified.
- What did you say? - I'm excited! Ok, you got it?
Babe, grab the straight— Babe, stop! How do I stop? Babe, I'm starting to think that you don't know how to ski.
No, I— I know how to ski. - How do I stand up? - I got you.
Ah! Oh, no. Babe, stop!
Babe, help! Thea, make me stop. Ok.
I got you. How do I stop? Legs together!
Legs closed, legs closed! What, are they not closed? Yeah, skiing is so much fun.
Anyways, let's move on with the date! With so much to explore in this shopping metropolis, it felt like doing ten dates in one! From winning prizes in an arcade… …getting a hole-in-one in mini golf… - Look at that!
- Yeah! …or building each other custom teddy bears. I love it.
And where I normally do these kinds of videos by myself or with my friends, doing this with the person I love most was kind of magical. Being able to do pretty much anything you could ever want to do on a date— It felt like being a kid in a candy store …literally! Ooh, chocolate.
Whoa. What is this? Uh.
Hey, ma'am? What is this? They're Hershey's.
Can we replace these with Feastables? Sure. Ok.
Oh! Much better! If you haven’t already, try Feastables.
It's the best-tasting chocolate on the planet. Let's keep the date going. We now have an entire waterpark to ourselves, and we just wanna take a relaxing swim together.
Isn't it crazy that we're in the middle of a mall? It's like as big as the ocean. Up next, we actually got Madison Beer to go on a date with Nolan.
Do you think Nolan has a chance with her? We're about to find out. For the $250,000 date, Madison Beer, the two-time Grammy nominee, platinum-selling artist, with over 3.
5 billion streams worldwide, is going on a date with… my awkward friend Nolan. - Hello! - Hey.
- Great to meet you. - How are you? Nice to meet you.
And while Nolan is on his date with Madison Beer, me and Tareq are currently tucked away in the bathroom with a walkie that communicates directly to a mic in Nolan's ear. Where are you from? - I'm from Long Island.
- New York? Yes. Where are you from?
Nebraska. Not much out there besides corn. - Cool.
- Yeah. No, he's talking about corn! In this seven years I've known Nolan, I have never seen him this nervous before.
So to help Nolan out, I spent $250,000 on Madison's dream date. From driving her favorite car, getting VIP treatment at an MLB game, and an over-the-top sushi dinner, all to give Nolan the best shot of securing a second date. Tell her you like her outfit.
A great outfit. Thank you. We told the waiter to help us wingman Nolan.
I'll be your server. Welcome to Bar Siesta. You guys look amazing.
I like your shoes my man. Dude, thank you. But it was quickly clear that it wasn't working.
How's the weather? How's the weather? Cool.
He’s falling apart. Nolan is not used to talking to attractive women. - You've watched the videos before?
- I watch all the videos. What's your favorite video? The one where they were underground for 100 days.
Madison Beer watches our videos. I never expected that. Same.
I don't really eat meat. Vegan? Vegetarian?
Pescatarian, 'cause I love sushi. They're getting to know each other, this is nice. - Sorry, I just got lost in your eyes.
- Aw, that's so sweet. Ohh, he hit it! He took the shot!
I was staring into the abyss. I don't… - Oh, not my eyes? - No.
As they finished eating, I had one last idea to help Nolan. I want you to tip the waiter $10,000. My card is in your wallet.
That guy was so nice. I think we should tip $10,000. I would love nothing more.
- Nolan has a gift for you. - We left a little something for you. Wait, are you guys serious?
- Thank you. - I appreciate it. - Here are the keys.
- Thank you. Let's hit it. Madison really loves animals, so their next stop on their date is an animal farm.
Nolan's only problem now was that the petting zoo was an hour drive away. Me and Tareq are still listening in. What's it like going up in front of thousands and thousands of people?
I just love my fans. They're the reason I get to do stuff like this and live my dreams. He's warming up and he's getting better with time.
We made it to the second part of the date. The Gentle Barn, a sanctuary that rescues abused animals. What made you start loving animals so much?
I have a lot of anxiety, and I feel like they just are a calming reminder of peace. I feel a sense of calm around you. You are smooth with it.
But visiting animals wasn't the only thing on our agenda. They're gonna give you guys $25,000, and I'm actually going to match them, and I’m gonna give you another 25,000. And then it was time for me to ask an important question.
You two ready to head to an Angels baseball game? - Let's do it. - Sure am.
Do you mind if me and my fiancee join you guys for the next part of the date? Am I allowed to say no? No, 'cause I paid for it.
I mean, you paid for it, right? And then we had an entire suite to ourselves at an Angels game. This view of the game is insane.
We got custom jerseys with our names on the back. And after almost all of us made it on the jumbotron… a crowd began forming around us. You'll be in a video, say "Hi.
" Anyways, we should probably head to the next part of this date. And for the final part of the $250,000 date— What are we doing, Nolan? Sushi dinner and an ice skating rink with some of the best sushi chefs on the earth.
I can definitely say I've never done anything like this. I gotcha, I gotcha. Thank you, Jimmy.
Tonight we prepared for you all a tasting menu. How much does this amount of fish cost? A couple thousand.
How do you think we got up to the 250K price tag? Definitely looks like my type of bite of sushi. Oh my God.
- That is so good. - Wow. And then we all enjoyed some of the best sushi I've ever had in my entire life.
This is the best date ever. - Thanks, Nolan. - Anytime.
The 250K date, I think we could all agree, was a lot of fun. Nolan, you had a question you wanted to ask. I do.
Oh, God. Oh, Jesus. Oh, God.
My shoe was just untied. Would you like to go on a second date to Disneyland with me? Yes.
Let's head on over! And now it is time for the most expensive grand finale date. We have Disneyland all to ourselves!
This is gonna be awesome. Let's go ride some rides! Disney won't just hand over their keys to anyone, but for this once-in-a-lifetime date, we were given the entire park for one night.
And with so much to do, we had to bring the boys, our friends from the island, and of course… Madison and Nolan. Yo, once we’re at the top, this is gonna have a crazy view. But our first stop is this absolutely insane Star Wars ride.
All right, that's cool. Holy smokes! Look how big this is!
Normally, people can wait hours for this ride, but my friends and I walked right in. Yo, strap in. All right, who's ready for the Star Wars ride?
Is now a bad time to mention I haven't seen the movies? What? This is crazy!
How did Disney build all this? This is wild. Oh my Gosh.
Nolan, protect Madison! Yo, can you believe we're doing this right now? Yeah, this is insane!
- That was awesome. - Once in a lifetime! This is crazy!
That was amazing! Every other cart was empty. We have this whole place to ourselves.
Disneyland is awesome! That was sick! And after that ride, what could be cooler… …than building your own lightsaber?
Oh, yeah! Coolest lightsaber! Up next, we're all gonna ride this giant Ferris Wheel.
We're back to where this video started. You could say it went full circle. I've never been on a Ferris Wheel that looks like that!
Yeah, this is massive! It feels like we're stepping into an old movie. Come on in, babe.
This is like the $1 date, but in Disneyland and much bigger. Much bigger! You can see the entire park up here.
Wow! How does this compare to our $1 date? I mean, it's so much better.
It's very romantic here in Disney. Wonder what Nolan and Madison are doing. Fist bump.
Let's go. Things are not looking good for Nolan right now. I can't wait to play games.
Yeah, that sounds fun. - Are you gonna win me something? - Of course.
Yay! Are you gonna win me something? Oh, you betcha!
Let's go! With his eye on the prize, Nolan challenged me and Chandler to a friendly competition. This is what you're competing for.
- A worm? Babe, do you want that worm? - Yes, I really want it.
Ok, boys, I'm gonna have to win this one. - All right, I wanna win this for you. - Please.
3, 2, 1… Go! - Nolan! - First one, first one.
Let's go! It's, like, curving. Two!
That's two! You need three to win. This is the grand prize.
It's all yours. For you. You can feel the tension in the air right now.
Gah, come here! But you know I couldn't lose to Nolan like that. Yes!
Yes! Oh my goodness! Let's run it back!
Yes! - Yay! - Here y’go, babe.
The Three P. Here we go! We won again!
That was fun! It's fun winning. There are no words to describe how special it is to have Disneyland all to ourselves.
And I think we all made memories that are gonna last a lifetime. Whoa, babe. There's a puddle.
You're a gentleman! No wet feet for you. Take notes, boys.
And to wrap things up, we have one final surprise. We're gonna be eating dinner in front of the Disney castle. - Oh my!
- What? All right, I don't know why Disney's going all out for us, but thank you guys. - Oh my gosh.
- Wow! - This is crazy. -This is beautiful!
Everyone, come on, sit down. Cheers to the greatest date in history. Cheers!
Yes! This was an awesome night. I'm glad I can enjoy it with all of you.
Cheers! Of all the dates I took you on, which one was your favorite? Definitely this one.
Yeah? Yeah, ‘cause everybody's here. We should do this more!
Rent all of Disneyland? Yeah. That was awesome.
And to wrap up the video, for the first time in Disney's history, they're going to do a private parade for all of us. Let's head on over. I gotta say, this date is gonna be so hard to top.
Huge thanks to Disney for absolutely blowing our minds with this experience. This was truly a once in a lifetime. If you don't have notifications on, make sure you turn ‘em on so you don't ever miss a video.
Chandler— Subscribe!
