Valentine's Day, Feb 14th, 2026 Jessica Holter and The Punany Poets present Love in the Upper Room A Black Date Night in Winter White on the South Side of Chicago

Jessica GGB Holter
Jan 8
3 min read

The Punany Poets Black Date Night, Love in the Upper Room Saturday, February 14th, 2026 Valentine's Day

Valentine’s Day often brings the same old dinner-and-movie routine. But what if you could step into a playful, immersive experience that feels like a romantic comedy come to life? On Chicago’s South Side, Love in the Upper Room offers just that—a unique Valentine’s date night that blends laughter, connection, and community in a vibrant, pressure-free setting. This event invites couples and singles alike to celebrate love with fun activities, a BYOB policy, and a complimentary Ice Bar by Chi City Cafe. Here’s why this Rom~Com experience is the perfect way to make your Valentine’s Day unforgettable.

💘 Love in the Upper Room — A Coffy Box Rom~Com

$66.63

February 14, 2026, 7:00 – 8:30 PM CSTUrban Society Enterprise

This Valentine's Day... Fall in Love Again!

From the moment you enter Love in the Upper Room, the vibe is lighthearted and welcoming. The event space is designed to feel like the set of a romantic comedy, with cozy seating areas, soft lighting, and quirky Valentine’s decor that sparks conversation and smiles. Unlike traditional Valentine’s events, this one encourages guests to relax and be themselves.

One of the standout features is the BYOB policy, which lets you bring your favorite drinks to enjoy throughout the evening. Whether you prefer wine, craft beer, or a special cocktail you’ve crafted at home, you’re free to sip and savor as you mingle. This adds a casual, homey touch that helps break the ice and keeps the mood fun.

Adding to the festive spirit is the complimentary Ice Bar by Chi City Cafe. This unique feature offers guests a chance to enjoy cool refreshments and specialty drinks served in an icy setting, creating a refreshing contrast to the warm, inviting room. It’s a perfect spot to pause, chat, and enjoy a creative beverage while soaking in the event’s charm.

Engaging Activities That Spark Connection and Laughter

Love in the Upper Room is not just about the setting—it’s about the experiences that bring people together. The event features several interactive activities designed to entertain and encourage connection without pressure.

Blindfolded Challenges

These fun, lighthearted games test trust and communication between partners or new acquaintances. Whether it’s guiding a partner through a simple task or guessing objects by touch, these challenges create memorable moments and plenty of smiles.

Pucker Up Butter Cup

This cheeky contest keeps things sweet and fun, inviting couples to show off their best (and most innocent) smooches. It’s a humorous way to celebrate affection and adds a bit of friendly competition to the night.

Each activity is designed to keep the atmosphere relaxed and enjoyable, focusing on shared experiences rather than performance or pressure. The goal is to foster genuine connection and laughter, making everyone feel included and valued.

Celebrating Love, Connection, and Community

What truly sets Love in the Upper Room apart is its emphasis on community and connection. This event is not just for couples but for anyone who wants to celebrate love in all its forms. Whether you’re single, dating, or married, the night offers a space to meet new people, deepen existing relationships, and enjoy the warmth of a supportive group.

The event’s organizers have created a space where guests can be themselves without the usual Valentine’s Day expectations. There’s no pressure to impress or perform—just an invitation to enjoy the moment, share laughter, and celebrate the joy of human connection.

This focus on inclusivity and fun makes Love in the Upper Room a standout choice for those looking to do something different this Valentine’s Day. It’s a reminder that love is not just about romance but about community, friendship, and shared happiness.