The Insider’s Market

Expert advice and exclusive tips from our matchmakers.

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The Art of Real Connection: Bringing Back In-Person Dating

We live in a world where digital interactions have replaced real conversations—but does it have to be that way? At Off Market, we believe nothing compares to face-to-face connection.

Learn how we’re bringing back intentional, in-person dating in Chicago—and why it’s more meaningful than any algorithm.

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5 Confidence Hacks for a Successful First Date

First dates shouldn’t feel like job interviews. With the right mindset and a few confidence-boosting strategies, you can walk into any date feeling calm, comfortable, and ready to connect. Discover 5 practical hacks that will help you feel your best and enjoy the dating experience.

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Why Dating Apps Aren’t Working for You (And What to Do Instead)

Dating apps promised to make finding love easier, but for many, they’ve only made it more frustrating. If you’re tired of endless swiping and shallow connections, you’re not alone. In this post, we break down why dating apps aren’t working—and how Off Market can help you find meaningful, in-person connections without the burnout.

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