Relationship guide
Relationship questions, answered honestly.
A private conversation for the relationship questions you can't ask anyone else — breakups, an ex you can't stop thinking about, situationships, intimacy and trust, or the hard conversation you're still rehearsing. Here's everything people ask before they start.
The honest FAQ
What is Dorothy Relationship?
A private chat where you talk through one relationship with honest advice — from "is he into me?" to whether it's time to leave. Dorothy answers like a candid friend who remembers the whole story, not a generic advice column.
Is it free to start?
Yes — you can start asking for free, no card required. When you run out of free replies, the one-time $29.90 Curiosity Pack adds 5 Astro Dice rolls and 30 more replies.
What are Astro Dice?
A playful divination game inside the chat: each roll lands a planet, a sign and a house — for example Venus in Scorpio in the 7th — and Dorothy reads that combination back into your situation, like a mini astrology reading you can react to.
Can I ask about a breakup or my ex?
Yes — it's one of the most common reasons people come. Getting over someone, no-contact days, whether to answer that 1am text, on-off patterns you keep repeating, or trust and intimacy questions you'd rather not hand to a friend. It also works as a rehearsal space before a hard conversation.
Does Dorothy remember our conversation?
Yes. Your relationship gets its own private file: earlier questions stay in context, Dorothy checks summaries with you, and long-term review shows what changed — so the conversation picks up where it left off instead of starting over.
Is it private?
Yes. Everything travels over TLS, sensitive server content is encrypted at rest, nothing is used for model training, and server copies are kept at most 90 days. You can export or delete your data at any time.
Open the Relationship Room
The chat itself is one tap away — free to start, private by design, and it remembers your whole story between sessions.
Start talking — free