Date Night: Angelo’s Wine Bar + The Recommendation

During the summer months, date night dining al fresco is one of life’s greatest joys. Conversation doesn’t reverberate in a crowded room but instead floats on the breeze as people lean back a little more in their chairs. Diners linger longer over chilled glasses of dry white wine, settling into a spot that is only available a few months out of the year. After dinner, a couple is ready for a bit of adventure and drama. The combination of Angelo’s Wine Bar and The Recommendation at Windy City Playhouse strikes the perfect balance of laid back and intense, relaxed and though-provoking.

Date night- Angelo's + The Recommendation

Angelo’s Wine Bar

Albany Park- 3026 W. Montrose

After seeing the decor and upscale feel of this eatery, you would never guess that Angelo’s Wine Bar has been around since 1962. Although the offerings have changed, the charm of the establishment has only increased. The staff greeted us warmly and we were able to have a pick of seating on a Sunday evening. The patio is simple yet elegant, bistro lights strung atop the fenced-in perimeter of the dining area and surrounded by brightly-colored flowers. Since our show started at 6 pm, we had time for a brief appetizer before hopping over to Windy City Playhouse to continue our date night.

Outdoor Patio at Angelo's Wine Bar- Chicago

Date Night Food and Drinks

I am the type of person who will ALWAYS order the sampler if such a menu item is available. At a brewery, I always love the lineup of child-size glasses nestled in a wood paddle so I can compare, contrast and find my favorite. Angelo’s offered a Flight & Bite, which included five 2 oz. pours of their wine on tap paired with five mini appetizers for $22. The wines were incredibly varied, ranging from a smooth and slightly spicy Grenache-Syrah-Mourvedre blend to a light and airy GrĂ¼ner Veltliner. Bites included craft sausage, Proscuitto, smoked cheese, Marcona almonds and more.

Wine and Appetizer Pairing at Angelo's Wine Bar- Chicago

After the show ended at 8:30, we scooted back to Angelo’s before last kitchen call at 9 pm to conclude our date night. I had spied Cacio e Pepe on the menu, which has been gaining popularity as a simple yet decadent dish made with three simple ingredients. My husband dined on their pan-seared scallops which included slightly crispy cauliflower, feta, and olives. Both dishes were divine, mine in its executed-to-perfection simplicity and his in the marriage of salty and savory flavors.


Angelo’s definitely has their share of specials. From “Taste of the Mondays” (featuring 1/2 off all 30 wines by the glass) to the weekend brunch all-you-can-drink Mimosa or Bloody Mary Brunch with purchase of a shared plate, there is something every day of the week. Bears fan? They also have $5 draft beers on game days, so the sports/beer fan in your relationship can be happy while satisfying the fine wine/dining partner.

The Recommendation

Windy City Playhouse- 3014 W. Irving Park Rd.
Tickets: $65-$100; sign up for the Rush Ticket List for potential day of tickets at half-off

The Bar

After a little fine wine and dine, you can scoot on over to the Windy City Playhouse mere minutes away. Parking has always been easy for me- there are plenty of spots along Irving Park on both sides. As you walk into the playhouse, you are greeted by music in the period of the show (Party Like a Rockstar, anyone?). Sidle up to the bar and peruse the specialty cocktail list, which includes show-themed libations such as Combination Pizza Hut & Taco Bell and The Drunk Tank. I love to keep these in mind and see where they fit into the performance. Cocktails are available for purchase before the show, during the 20-minute intermission, and after the final scene. My favorite bartender, Nolan, is onsite to entertain and whip up delicious concoctions.

The show starts promptly at the set time in an unexpected way, so pay attention and be prepared to immerse yourself in this story of privilege and the disparity between what is fair and what is real.

The Premise of “The Recommendation”

Do you know someone for whom everything simply falls into place? Especially early on in life, when their parents artfully arrange their path without thought of or principles or legitimate qualifications? Some beings are able to skate through life with charm and connections, not aware of the challenges and roadblocks of the hoi polloi. This is where The Recommendation starts- with Aaron Feldman as the golden boy entering his Freshman year in college. He is paired with Iskinder Ioduoko who does not share the same privileges and benefits that Feldman has reaped his entire life.

The Recommendation- immersive theater in Chicago
Photo Credit: Michael Brosilow

Although from vastly different backgrounds, the pair becomes friendly, moving through their college experience with humor that will bring back your own memories of this period in life. You watch as Aaron and Iskinder graduate to young adulthood, each set on their own path to (in)dependence.

The Recommendation at Windy City Playhouse
Photo Credit: Michael Brosilow

Your Date Night Experience

The audience moves from room to room in the show instead of just the actors shifting scenes, which emphasizes the immersive nature of this presentation. Limited to 34 audience members, each participant (yes, you do get to participate on an experiential level) gains a true sense of being a part of the story. Seating ranges from a dorm room bed to a jail cell bench, keeping you on your toes and more than a fly on the wall. You are completely involved in each scenario and emotionally-charged scene. Snack and beverages for the audience are interspersed throughout the show that incorporates different themes and moods, creating a unique date night experience.

The Recommendation at Windy City Playhouse
Photo Credit- Michael Brosilow

The actors are intense in parts, lighthearted and carefree in others. Since you are up close and personal, you are able to observe their body language, eye contact and microexpressions like no other performance you have experienced. I felt Feldman’s fear through the animal-in-a-cage expression, Iskinder’s faux confidence through his ramrod posture and stiff movements, and the insecurity and yearning of another character, Dwight Barnes, in his hunched shoulders and fidgeting.

Questions to Ponder

This show, dubbed a “psychological thriller” by many, inevitably raises questions about the fairness of life. Here are a few that came up for me- I love discussing an intelligent performance during our date night.

Have you been asked for help by someone in need, but paused to consider the ramifications for yourself?

How has your privilege or lack thereof influenced your life path?

How can someone seemingly stuck in a circle of criminal action or labeled a criminal break their cycle or stigma?

If you were applying for a job, would you accept help from an outside party even though you aren’t the most qualified for the position? If you did, do you think that makes you part of the problem or are you just taking advantage of opportunities?

How do recommendations or referrals tilt the playfield? Do you believe all recommendations or you take them with a grain of salt?

Overall Thoughts

Overall, this type of immersive theatre production is my absolute favorite and makes an entertaining date night. You are entertained and involved, often rapt and completely engrossed. Actors might speak to you on occasion, asking you a question or having you hold on to a prop. The only requests are that you don’t speak directly to an actor unless spoken to, and do not touch them as they move about the set. Keep an open mind, try to relate to different characters and situations, and stay curious.

Cheers to an experience for both your taste buds and your mind at these two excellent venues!

Disclosure: I received complimentary tickets to The Recommendation for review purposes. All opinions are honest and my own, as always.