We are back with a no-holds-barred Best of Dear Damona episode—because when it comes to texting mishaps, mixed signals, and dating curveballs, this one hits home every time.

In this candid conversation, Damona answers some of your juiciest dating dilemmas—from the accidental text that lands in the wrong inbox to what it really means when someone texts you “hey you” at 11:30 PM. She shares smart, compassionate advice on navigating confusing signals, staying grounded, and owning your truth in the dating game.

What you’ll learn:

How to respond and recover when you send the wrong text to your date

Whether it’s okay to ask for better photos—and how to do it playfully

The real timeline for exclusivity (spoiler: you don’t have to rush)

Why it’s okay to date multiple people—and how to know when to choose

How to disclose chronic conditions or disabilities with confidence

Why shared values matter more than shared hobbies

This episode is part of our Rewind Series, where we revisit some of the most powerful and timeless conversations from the Dates & Mates vault.

Subscribe to get every rewind episode and our Spring special bonus episodes the minute they are available.

DM Damona your questions on Instagram @damonahoffman or text 424-246-6255 to be featured on a future episode.

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