Rehearse awkward talks — what to say and how to say it. AI plays the other person, suggests lines when you're stuck, and coaches your tone so you walk in ready.
Best for breakups, work, family, neighbours, and everyday calls — one scene at a time, not court cases or long legal prep. For formal rights and process, try Pocket Lawyer.
Pick a situation — practise the talk, not the whole case file.
How it works
Legal rights or court process? Tricky Chats is for practising what to say. Try our sister site Pocket Lawyer for UK legal information (not advice).
Reply top-ups add
Reviewing your conversation to prepare feedback.
This may take a few seconds.
Synthesising the voice — usually a few seconds.
Before you start
Tricky Chats helps you rehearse one awkward conversation — what to say and how to say it at work, at home, or on the phone. The other person is played by AI, so you can try different lines before the real talk.
It's a practice tool, not professional advice or emergency support. It is not for legal rights, court process, or building a whole case — for that, use our sister site Pocket Lawyer (general UK legal information, not legal advice) or a qualified professional. If you or someone else is in immediate danger, contact local emergency services.
You can install Tricky Chats as an app on your device for quicker access from your home screen.
Legal stuff
Last updated: 30 May 2026
Tricky Chats ("the app", "we", "us", "our") is a practice tool that lets you run through tricky or awkward real-life conversations with an AI playing the role of the other person. By accessing or using the app you agree to these Terms & Conditions. If you do not agree, please do not use the app.
Tricky Chats is provided for general practice, entertainment and educational purposes only. It is not professional advice of any kind, including but not limited to legal, financial, medical, psychological, therapeutic, insurance, employment or counselling advice. The other person in every conversation is simulated by artificial intelligence and does not represent a real person, organisation or professional.
Nothing in the app should be relied upon when making real-world decisions. You should always seek advice from an appropriately qualified professional before acting on anything discussed in or suggested by the app.
Tricky Chats and Pocket Lawyer ( pocketlawyer.life ) are separate products operated by us. Tricky Chats is for rehearsing what to say in difficult conversations. Pocket Lawyer is for UK-focused general legal information (letters, process, options) — still not regulated legal advice, representation, or a solicitor–client relationship.
If your question is mainly about legal rights, court or tribunal process, or formal complaints, use Pocket Lawyer or a qualified professional — not Tricky Chats. We are not liable for treating Tricky Chats as a substitute for legal advice or for any outcome if you rely on AI-generated roleplay or coaching instead of professional help where that was required.
Tricky Chats is not a crisis or emergency service. If you or someone else is in immediate danger, call 999 (UK) or your local emergency number.
If you need urgent mental-health support in the UK, you can contact Samaritans on 116 123 (free, 24/7) or visit samaritans.org. For urgent medical advice in the UK, call NHS 111.
Responses, suggested lines, feedback, images and voices are generated automatically and may be inaccurate, incomplete, offensive or misleading. We do not review or guarantee any content produced by the app, and you use it entirely at your own discretion and risk.
To the fullest extent permitted by law, we exclude all warranties, conditions and representations relating to the app, which is provided on an "as is" and "as available" basis.
To the fullest extent permitted by law, we (together with our owners, operators, employees, suppliers and partners) accept no liability for any loss, damage, cost or injury — whether direct, indirect, incidental, consequential or otherwise — arising out of or in connection with your use of, or inability to use, the app, or any reliance on its content. This includes, without limitation, any outcome of a real conversation, decision, action or inaction taken on the basis of anything you saw, read or did in the app.
Nothing in these Terms excludes or limits liability that cannot be excluded or limited under applicable law.
You agree to use the app lawfully and not to misuse it, attempt to disrupt it, or use it to harass, harm or deceive others. We may suspend or withdraw access at any time without notice.
The app uses cookies and browser storage that are necessary for it to work. These are not used for advertising. Examples include:
By continuing to use the app, or by selecting "Accept" on the cookie banner, you consent to this use where required by law. You can clear cookies and site data in your browser at any time; some features may stop working if you do. See our Privacy Policy for more detail on server data and retention.
Paid reply top-ups unlock features such as generated portraits, read-aloud voice, per-line coaching during a chat, and continuing a saved conversation from PDF. Prices are shown at checkout (currently from £5 for 60 replies, £15 for 200, and £30 for 500 — one-time, no subscription).
Payment is processed by Stripe. We do not store your full card details on our server. After purchase you receive a license key by email; paste it on each device to use your reply balance. Top-ups stack on the same key.
Premium features that call AI or speech APIs are subject to fair use. We may suspend keys that are shared publicly, abused, or used to attempt to bypass technical limits.
Because reply top-ups are delivered digitally (license key) as soon as payment succeeds, statutory withdrawal rights may not apply once the key is issued — check applicable consumer law in your country.
If you bought by mistake or the key does not work, email TrickyChatsAdmin@gmail.com within 14 days with your purchase email and we will try to help (replacement key or refund at our discretion where Stripe allows). Top-ups are one-time — there is no subscription or auto-renewal.
You must be at least 13 years old to use Tricky Chats. If you are under 18, you should use the app with a parent or guardian's permission. The app includes scenarios about adult life (work, relationships, housing, health calls) that may not be suitable for younger children.
Tricky Chats is operated from the United Kingdom. For support, billing, or legal queries contact TrickyChatsAdmin@gmail.com. Website: https://trickychats.life.
We may update these Terms from time to time. Continued use of the app after any change means you accept the updated Terms. Material changes to privacy practices are described in our Privacy Policy.
Privacy Policy
Last updated: 31 May 2026
Tricky Chats ("we", "us", "our") is a web app at trickychats.life that helps you rehearse difficult everyday conversations with AI. This Privacy Policy explains what information we process when you use the app and your choices.
On our server
sessions.db). This lets the conversation continue during your visit
and powers features such as suggested lines and feedback.
In your browser (local storage & cookies)
We do not sell your personal data and we do not use third-party advertising trackers on the app.
To generate replies, coaching, speech, and images we send relevant parts of your scenario and conversation to AI providers configured on our server (for example Google Gemini and/or OpenAI). Those providers process data under their own terms and privacy policies.
Premium checkout may be processed by Lemon Squeezy (or another payment provider we configure). License validation may call Lemon Squeezy's servers.
Transactional email (license keys) is sent through the SMTP service configured in our environment (for example Gmail or your domain host).
If you are in the UK or EEA you may have rights to access, rectify, erase, restrict, or object to processing, and to data portability, subject to exceptions. Because most practice data is tied to an anonymous session id in your browser, the easiest way to erase it is to clear site data for trickychats.life. If you bought a reply top-up, the email with your license key and invoice includes a link to request deletion of server-side data tied to your purchase email. Other questions: contact us using the details below.
You may complain to the Information Commissioner's Office (ICO) if you believe we have handled your data unlawfully.
Tricky Chats is intended for users aged 13 and over. It is not designed for children under 13 and we do not knowingly collect their data. If you believe a child under 13 has used the app, please contact us so we can delete associated server sessions where possible.
Our server may be in the UK or EU. AI and payment providers may process data in other countries under their standard contractual safeguards.
We may update this policy from time to time. The "Last updated" date at the top will change when we do. Continued use of the app after an update means you accept the revised policy.
Questions about privacy or your data: TrickyChatsAdmin@gmail.com. See also our Terms & Conditions.
Notice
Sign in
Coach feedback
No coach feedback yet. Tap the coach icon beside one of your lines, or use How did I do? when it appears.
Suggested responses
Pick the response you think is most useful — it'll drop into your line so you can edit it (if you like) and click Send.
Generating options…
Leave this chat?
You haven't saved this conversation as a PDF yet. On the free plan, saving is how you get your full coaching notes. Save now if you might want to read them later.
Save your chat
Your session PDF is ready. Save it somewhere you can find it later.
With Premium, you can continue this chat later — tap Continue Chat in the header and upload the PDF you save. Your scenario, settings, and conversation are stored in the file.
Continue Chat
Picking up where you left off — from a PDF you saved after a practice chat — is a Premium feature.
On the free plan you can practice up to 8 of your replies per chat, then Save PDF at the end for full coaching. Upgrade for 25 replies per chat and to upload that PDF later with Continue Chat.
Continue Chat
Pick up a practice session you saved earlier. You'll choose a PDF exported from Tricky Chats (use Save PDF at the end of a chat).
What happens next
Install app
Install adds Tricky Chats to your home screen — like an app icon you tap to open next time. The install is free; you can keep using the free plan or upgrade when you're ready.
Premium adds:
Top up your replies
Top up as you go. No annoying subscription.
Already have a key?
Paste the key from your purchase email to add replies on this device.
We'll email your license key and invoice to this address.
Enter your email above first — your card details will load below, processed securely by Stripe.
Completing your purchase…
Confirming payment and preparing your license key.
Top-up complete
Your license key is active on this device.
Check your junk or spam folder for mail from TrickyChatsAdmin@gmail.com if the license email is not in your inbox within a few minutes. Mark it as not junk and add TrickyChatsAdmin@gmail.com to your contacts so future mail arrives correctly. Your key is below — you do not need the email to use Premium on this device.
Your license key
Reply top-ups
Free: 40 replies in total, up to 8 per chat. After your first purchase, faces, voice, coaching, and Continue from PDF unlock — and there is no per-chat cap, only your reply balance.
60 replies
£5 one-time
200 replies Popular
£15 one-time
500 replies
£30 one-time
Free plan: 40 replies in total, up to 8 per chat.
Paste the key from your purchase email (format TC5-… or legacy TC1-…). Check junk or spam for mail from TrickyChatsAdmin@gmail.com.
Premium unlocked
Paid features and extra replies are now on. Enjoy.
Set the scene
The questions marked optional you can skip — they just help the other person feel real.
We use cookies and local storage needed to run the app and remember your preferences. See our Privacy Policy and Legal stuff.