There are a few precious times a year when you get a compelling reason to ask a client to hang out. As riveting as it may be, your boss happening to be visiting from NYC does not count.  

Halloween, on the other hand, is one of those rare moments. Whether it’s classy, terrifying, or wholesome, here are three very different ways to do Halloween with your clients this year.

— Robbie

The Obscure is a boutique distillery that operates an elegant live storytelling and cocktail experience in the Arts District. 

From a Halloween standpoint, this is less guy-chasing-you-with-a-chainsaw and more of a classy, candlelit evening that leans into the New Orleans haunted-mansion aesthetic. 

The two-hour performance guides you through a tasting of three of their house-distilled spirits and three cocktails (they also offer mocktails). Your host tells the history, mythology, and bizarro inspiration behind what you're drinking alongside the theatrical elements going on around you. 

Their Insta has some fun videos like this that walk you through what the experience looks and feels like.  

Food isn’t served during the show, but there is a well-reviewed Cajun spot associated with the venue called The Rising Sun next door that you can check out beforehand. The website says they’re closed for scheduled maintenance, but I confirmed that they are indeed open from 6-10pm on Wednesdays and Thursdays. If you have any issues, Zinc is another good option around the corner.

Since there’s a decent amount of alcohol involved, I’d recommend eating beforehand and strongly consider getting Uber codes for your clients. 

When booking, you’ll notice there are different Chapters you can choose from. These are the stories and drinks programs you’ll experience. They told me that any of them are great for first-time attendees, so choose whichever suits the timing of your group.

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Added value: I like this one because it’s essentially a fun night at a moody, seasonal cocktail bar where there’s enough going on to make it feel like an occasion, but you still get a chance to actually talk and connect with your clients.

Delusion: Den of the Mosquito is a high–production, interactive horror play set inside the historic Beckett Mansion in West Adams.

If you have a client who loves horror, immersive theater, or is simply game for doing something completely different, this is an excellent Halloween idea to consider.

The Delusion team has been operating highly regarded, premium immersive theater experiences since 2011. As I was looking for unique Halloween ideas, this one kept coming up. 

This isn't a haunted house where you shuffle through a maze while people jump out at you. You and your group are actually part of the story and can influence where it goes. This year’s story takes place in 1920s New Orleans, and you are agents investigating a string of supernatural happenings. Here’s a trailer of the storyline for a sense of what you’re getting into. 

The actual Delusion experience takes about 50 minutes, but they recommend arriving early to grab a drink and settle into the “Open World,” a free-roam scavenger hunt that takes about 30–60 minutes to explore. You can also grab a bite. Leaning into the New Orleans theme, they have Creole-style food on site like gumbo, sausages, and beignets.

After you finish the actual immersive play, you can catch up with your crew, thank god you’re all still in one piece, and explore more of the Open World if you missed it earlier.

This one is supposed to be legitimately scary. Check out the full FAQs for the specifics, but if your client hates horror, physical activity (stairs, tight spaces, crawling), or the idea of participating in immersive theater, this is not your jam.

The flip side is that if they are into this type of experience, you’ll likely be the only one suggesting it, and you’ll have a hell of a shared memory to connect you going forward. 

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Added value: I’ve personally never done anything like this, and I imagine most clients haven’t either. Mutual risk is part of the idea here. You’re both out of your depth wandering around a dark mansion together trying to figure out what the hell is going on. For the right client, you’ll be laughing about that shared memory for a long time in a way that a more typical outing couldn’t achieve.

Carved is a nighttime Halloween walk through Descanso Gardens filled with light installations, old-timey fall stuff (eg. a short hay maze for kids), and seasonal artwork including some remarkably creative pumpkin carvings.

This is a great option for anyone interested in an experience that falls on the more wholesome end of the Halloween activity spectrum. It’s also extremely kid-friendly and worth considering if both you and your clients have kids and you’re open to getting everyone together for a weeknight wander through the gardens. 

You’ll follow a guided path that takes about an hour and you can grab a drink, hot chocolate, or food/desserts along the way. Here’s a quick Insta video for a sense of the experience.

If you want to make more of a night of it, the on-site restaurant, Farmhouse at Descanso, was recently renovated and has a strong farm-to-table menu.

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Added value: Most client entertaining experiences take you away from your family, and this is one of the rare ones where I think you can reasonably incorporate them. 

I’ve been to Carved the last few years including with a friend in the media world and her family. If you know a client well enough that inviting the family doesn’t feel weird, this is a totally different way to spend time together that can bond you in a more thoughtful way.

Ever been hanging with a client and conversation just runs dry? Whether it’s recent and topical, or general and evergreen, the Oasis is about giving you one idea for helping in that moment.

What was your best Halloween costume? 

Pretty straightforward topic with a lot of runway if you find yourself talking about Halloween. Everyone likely has one they’re proud of or at least one that they remember fondly. 

My best was when I went as the Publishers Clearing House guy. I put on a suit, made a huge check, got a few balloons, and proceeded to take “OMG I won $1M!” photos with everyone I could find. 

Being an economical and not forward-thinking guy in my 20s, I saved the giant check and trotted out the same costume the following two years until some girl I was trying to chat up called me out for having a check dated from two years ago. 🙃

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