Battle Boo Bakery: Where Military, Veterans & Locals Connect

Battle Boo Bakery isn’t speed dating. It’s an intentional Valentine’s experience built around connection, teamwork, and community.

Hosted by the Black Veterans Expo inside Strugglebeard Bakery, a Black veteran–owned business, this night brings together military, veterans, and other locals who care about how they show up and where their money goes.

Instead of awkward small talk, you’ll connect through competition-based activities like karaoke, card games, and portrait drawing. We’ve curated these activities to magnify how you communicate, support one another, and move as a team. That’s how bonds are built in the military, and it turns out it’s a pretty good way to build relationships too.

Three couples will be selected to receive a $50 first-date tab at a Black veteran–owned business of their choice. The idea is simple: if your connection starts here, your first date and the memories that follow stay rooted in community and keep your dollars circulating in places where you’re valued.

Whether you leave with a Battle Boo, a Battle Buddy (a new friend), or just a better sense of what you want, you’ll walk away having shown up with intention.

Come connect.
Compete.
And maybe become one of the top three couples.

RSVP required. 21+.

Please note: this event will be photographed and recorded by Treazure, L.L.C., The Black Veterans Expo, and event partners. By attending, you may appear in photos or video used for marketing, documentation, or press, without compensation. Photo & video consent is required at registration.

Info: Arrive, check in, and start connecting. You’ll receive a Battle-Boo Bingo card to help break the ice and guide your conversations as you mingle.
To make connecting easier, we’ll also use a simple, optional system in the room: different cup colors show whether you’re Active Duty, a Veteran, or a Local, and small dots on name tags signal whether you’re here for dating or open to friendship. It keeps things honest, light, and low-pressure so you can focus on connection instead of awkward questions.
Meet new people, compare notes, and decide who you want to team up with for the night. This is your warm-up—no pressure.

Info: Once you’ve chosen your Battle-Boo, it’s time to team up and compete. You’ll choose one of three activity tracks:
Karaoke – Chemistry over perfection. Who had the best energy together? The crowd decides.
Portrait Drawing – Each partner draws the other. Funny, borderline disrespectful, wildly accurate—that's none of our business lol. The crowd favorite wins.
Card Games – Choose from Spades, Uno, or another deck favorite. Best of 2/3 or 4/5—you set the rules.
One couple will be selected from each activity track to become our Top 3 Couples.

Info: During the final 30 minutes, we’ll vote for the crowd favorites from each activity.
You don’t have to decide your date location on the spot. You’ll have until February 28 to reach back out and start your $50 first-date tab at a Black veteran–owned business of your choice.
If you need help finding a spot, we can provide recommendations.
If you’d rather support a Black veteran–owned business that isn’t a restaurant, we’ll support that too.

Event Venue & Nearby Stays

Strugglebeardbakery, 5221 South Harper Court, Chicago, United States

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