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Happy Hour Ideas For Bosses By Alexis Davis

Happy Hour, but make it Bossy!

Sometimes there’s a negative stigma around bosses taking breaks. As a WOL boss, it is imperative to

take a moment to go out with friends to celebrate yourself even if isn’t a special occasion. When it

comes to taking breaks, who says they can only happen on the weekends? Here, at WOL we believe in

working hard but playing hard too. To be the best boss you can be, it is important to avoid burnout and

give yourself grace. Follow our guide to the best weekly happy hours in Washington, D.C. for an even

tastier reason to celebrate yourself during the middle of the week!

1. Ben’s Next Door

At this lively place in the heart of U Street, their happy hour is every day from 3-7 pm. Some of the local

favorites include their Hennessy Sangria and their Lemon Drip-Drip Martini. The Hennessy Sangria

includes Hennessy, brandy, Rioja wine, all-spice dram, and various fruit juices. The Lemon Drip-Drip is

their home take on a classic lemon drop and includes Malfy limon, vanilla, lemon, and Italicus. Their

happy hour food ranges from $4.95-7.95, talk about a steal! Some of the Happy Hour food standouts

include lump crab deviled eggs for our seafood lovers and the St. Louis dry rub ribs for those that like

their food from the land better.

2. dLena

The curators and owners of dLean know how to Mexican the right way! dLena is a perfect mix of upscale

and cozy. The exciting décor includes a variety of warm wooden tones throughout the restaurant with

low lights to help you relax or if you are with a romantic partner, it provides more intimacy. dLena’s

Happy Hour takes place in their bar area every day from 5-6:30 pm. As you’re reading this, you may be

wondering, how can you do Mexican without margaritas? Don’t worry! dLena has you covered with the

best margarita deals in the city. During their Happy Hour, all margaritas range from $6-7 with a signature

Mercado addition that includes serrano-infused Blanco tequila, passion fruit, agave, and hibiscus

rosemary foam. Going along with the $6 theme, the establishment also has habanero pepita salsa and

barbacoa tacos as a part of their Happy Hour that will leave you wishing you could eat Mexican 25/8!

3. Urban Roast DC

Urban Roast is one of the places that makes you instantly want to give it a 10/10 based on the overall

aesthetic. For our WOL bosses that love great food and drinks attached to a great opportunity to get a

bomb photo, Urban Roast was made for you! Their Happy Hour is from 2-6 pm. Some people focus on if

the cup is half empty or half full, at Urban Roast they only focus on if the cup is refillable! During their

Happy Hour, they have $8 sangria and $6 house wine which can be refillable under certain

circumstances. One of the highlights of Urban Roast includes its outdoor firepits. These firepits create

the perfect setting for our bosses that are not able to make Happy Hour until later in the day. With

summer coming to an end soon and fall on the horizon, Urban Roast will make the perfect transition

place to meet up with other bosses. Although it is not a part of their Happy Hour, their one-of-a-kind

s’mores are still worth the mention. You can roast your marshmallows over the firepit and choose from

a variety of s’mores flavors. One immediate attention grabber from the flavors is Urban Roast’s take on

the famous Girl Scout cookie Samoa including a caramello square and toasted coconut.

4. Bar Charley

Even as WOL bosses, we sometimes are not the most excited about Monday. Bar Charley gives us a new

reason to hit the ground running for the week with their all-night-long Happy Hour on Mondays! Bar

Charley is a very unknown place that usually isn’t too crowded, but after this great read, don’t be

surprised if you run into your favorite WOL boss here! Bar Charley makes each guest feel like they are in

their backyard with their picnic-style set up for those that chose to sit outside. Your fun Monday night

out can also be completed with some of Charley Cocktails. One of their signature drinks includes the

Which Doctor? This drink includes rum, pineapple, orange juice, lemon, demerara, bitters, and


Don’t forget WOL Boss, as you are navigating your week and determining how to be the most productive

you can be, it is important to take time to simply breathe. And who wouldn’t mind taking those deep

breaths in the midst of a relaxing happy hour? We can’t wait to see your take on your best causal happy

hour outfits as you pose in front of the listed aesthetics. See you at happy hour bosses!

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