Pop quiz; what does a century old cocktail, an Asian kid in a Jazz band, and an Artist who charges ugly people extra, all have in common? Answer; they’re all things we experienced on our dream date in New Orleans.
We decided to explore such adventures after reading Tim Ferriss’s Dream Date Challenge. He posed the questions; If you had to plan your ideal dream date weekend, what would you do? Where would you go? What adventures would you embark on? He asked readers to
He gave his favorite picks a first edition copy of his book, The 4-Hour Work Week. Then he posted a follow-up post where he challenged readers to pick one of the dream dates to do this past weekend.
That was just the kick-in-the-butt I needed to plan something for my wife and me. Luckily, one of the locations named was New Orleans, which is just under an hour away.
In this article, I’ll share with you our dream date weekend results, including how our dream date ended up being FREE, and some other recommendations on creating your own New Orleans dream date.
The Dream Date: New Orleans Weekend
The Budget: $500 or Less
The Plan: Take in the sights, tastes, and sounds of New Orleans culture. Relax and enjoy each other through conversation, laughter, and just being together.
Day 1: Off to a bumpy start
Drive to New Orleans - Charlene was really excited when I told her about our weekend. It’s been a rough couple of years (one I could dedicate an entire post to) and we desperately needed a getaway like this.
On our way we needed to get gas and pick up a couple of things at Wal-mart. To save time, I offered to run in and pick up the things we needed, while she filled up with gas. When I got out of the car I didn’t think about the large water bottle Charlene brought sitting beside me.
I didn’t realize the bottle tipped over when I got out. The passenger seat was completely flooded!. I knew she wanted me to drive, so the only option was for her to ride in the back seat the whole way.
We had a good laugh about me being the chauffeur and how funny we looked.
Check in at The W New Orleans - I reserved a room at The W, since it was close to much of what we had planned. New Orleans traffic was a pain with all the road construction, but we finally made it.
I pulled up to the hotel and it looked like the only thing offered was valet (which was completely crowded and backed up). I got out to confirm and they said that valet is in fact, all they offer. We figured $28 was too much to pay to wait for thirty plus minutes on valet. We remembered that Harrah’s offers free unlimited parking if you play.
Part of the plan was to enjoy playing some poker while we were in N.O. so we parked there. We ended up having to park on the roof of the parking garage which worked out well. We enjoyed a beautiful evening view of the city before making our way to check-in.
Go to the Loews Hotel, find Lu Brow, and order two Sazeracs - One of the recommendations on Tim’s blog was to go to the Swizzle Stick Lounge in the Loews Hotel and find Lu Brow, recognized as the best New Orleans bartender. Then, have her make two Sazeracs, one of the oldest cocktails in existence.
Unfortunately, Lu Brow was not there due to a loss in her family. We can certainly sympathize. Instead, Michael took care of us. He is a great guy and bartender. He gave us a history of the Sazerac as he prepared them, and made sure we felt right at home.
When he asked what brought us there, I couldn’t help but to tell him about the 4-Hour Work Week, Tim’s blog, and our adventure. He commented, “The 4-Hour Work Week huh? Sounds like a book I need.” Perhaps I made Mike a new Lifestyle Design convert.
We took our cocktails, which were ‘interesting’ to say-the-least, and found a cozy spot in the lounge. We talked, listened to beautiful music from the piano player and lounge singer, and took in the ambiance of the lounge. Before we knew it, time had flown by and we were off to enjoy some delicious food at Dickie Brennan’s Steakhouse.
Enjoy great food and conversation at Dickie Brennan’s Steakhouse - This wasn’t the restaurant recommended, but I wanted to customize the date to fit our own likes and dislikes, while still experiencing something new. We both love a good steak, so I decided we’d try the world renowned, Dickie Brennan’s Steakhouse.
It definitely lived up to our expectations. We enjoyed incredible Filet Mignon with Sauteed Shrimp. The steak could easily be cut with a fork, and almost melted in our mouths. Charlene made the comment that, “steak sauce would be an insult”.
We don’t know much about wine, so we opted to enjoy a beer with our meal. *Hears collective gasps from wine-lovers* Don’t worry, we’ll come around soon enough.
We talked about traveling the world, learning more about wine, and how much we love each other. We realized that moments like this should be sought after and never taken for granted.
Stroll through the beautiful display of Christmas at Miracle on Fulton Street - We left the
restaurant and walked down Bourbon Street, where we stood and enjoyed some good jazz, courtesy of these guys. My only question was, how did this Asian kid make the band?
We made our way to Miracle on Fulton Street, a beautiful local Christmas display. There we strolled, hand-in-hand, and talked some more. I couldn’t talk Charlene into sitting on Santa’s lap. I 
guess the effects of the Sazerac had worn off.
Poker at Harrah’s - We decided to go play some late-night poker at Harrah’s. We both love to play Texas Hold’em, the only game in the casino where you play aganist others and not the house. It’s a game that combines hand selection, math, and psychology. It also has a social element to it. We enjoyed laughing and talking with each other, and some new faces. We ended the night by making $95, minus what we spent on two Lucky Dogs (classic New Orleans chili hot dogs). Then we headed back to the hotel for some ‘alone time’.
Day 2: More fun and New Orleans culture
The French Quarter and Cafe Du Monde for beignets and Cafe Au Lait - We slept in, but finally managed to make our way to Cafe Du Monde. The cafe was completely packed, and it looked like we would be waiting forever for service. So we decided to grab a little lunch and then come back for beignets later.
We shared appetizers and a Philly Cheesteak while people-watching and talking about the rest of our day together. We noticed across the street was a Zoltaire machine. You should remember Zoltaire from the movie Big, where the kid makes the quarter in Zoltaire’s mouth and wishes to be “big”.
Subsequently, he wakes up as Forrest Gump, I mean Tom Hanks.
Anyway, that brought up the subject of what we would wish for if given the chance. After much discussion and contemplation I came up with “Good health, good friends, and a lifetime of breath-taking moments and adventures with my wife”.
We made our way through the French Quarter, looking and discussing the various artwork displayed around the park. We watched a street magician, and an entertaining group of guys doing various dances and stunts. Then, we listened to some great music outside Cafe Du Monde while we ate beignets and sipped cafe au lait without a care in the world.
We decided to end the day by going back to Harrah’s and try to win enough to pay for the weekend. And guess what? We did! After just a couple of hours of play we made $281. Here’s a breakdown of the numbers.
- Room at the W: $200
- Two Sazeracs w/ tip: $22
- Cab ride to restaurant: $8
- Dinner at Dickie Brennan’s: $80
- Lucky Dogs: $8
- Lunch: $20
- Beignets and Cafe Au Lait: $13
- Other tips for performers: $10
- Weekend Cost: $361
- - Poker Winnings: $376
- Total Dream Date Cost: -$15
Having a weekend full of fun, relaxation, and adventure with the love of your life, PRICELESS.
New Orleans date recommendations and what I would do differently
Not spend half the budget on a room - We’re not picky people, so looking back I should have found less expensive accommodations around the French Quarter. If you’re planning on exploring and experiencing the New Orleans culture as opposed to hanging out in the room, save your money and find a room somewhere else for around $100.
Take a carriage ride tour - They have several carriage ride tours that will carry you through the French Quarter starting at around $60 per half hour. The tour guide gives you the history of the area while you relax and take it all in. I hope we can do this our next New Orleans trip.
Get a custom portrait of yourselves - There are quite a few artists that do caricatures around the park. Prices are pretty reasonable from what I noticed. One artist had a funny sign that said “Ugly people $1 extra”. This is definitely on our to-do list for our next dream date.
Conclusion to a wonderful weekend
All-in-all it was a great weekend. I’m thankful that Tim Ferriss started the topic and that someone decided to post about New Orleans. It gave me the inspiration and boost I needed to plan a great spur-of-the-moment vacation.
It gave us a renewed appreciation for each other and living life to the fullest. I hope you’ll plan your own dream date getaway, there’s nothing like it!
If you have any other recommendations for things to do in New Orleans, please use the comments to share.