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.
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!