Valentine's Day Singles Event

Schedule

Sat Feb 14 2026 at 07:00 pm to 10:00 pm

Location

Union League Club | Chicago, IL

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Join us for an elevated singles gathering designed for genuine connection, in all the ways it can show up. This evening is for curious hearts and open minds, where a simple “yes” might lead to a romantic interest, a new friendship, a creative collaborator, an unexpected business connection, or a conversation that stays with you long after the night ends & reminds you what's possible when you show up.

This event isn’t about walking in with the expectation of meeting “the one.” It’s about saying yes to the experience itself. Yes to thoughtful conversation. Yes to easy chemistry. Yes to being in a room with people who are also choosing openness over assumption. Yes to connections you can’t fully predict yet.

Come dressed in cocktail attire, relax into the atmosphere, and trust that meaningful moments don’t always announce themselves in advance.

So often, fear tries to decide for us...assuming what an event will be like, who will be there, or what it might “say” about us. This night is an opportunity to quiet that noise, step out of assumption, and choose curiosity instead. No overthinking. No pressure. Just real people, great energy, and the freedom to see where connection might lead.

Join us in this welcoming space for authentic connection...and, the possibility of something unexpectedly wonderful.


Ticket Pricing: $85-$95

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Where is it happening?

Union League Club, 65 W Jackson Blvd, Chicago, IL 60604, United States

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