Ask any AI assistant to explain the confusing parts of a lease or contract

Pick one paragraph that confuses you

Open the contract and scroll until you hit a sentence that makes you pause — something with words like "indemnify," "perpetuity," "liquidated damages" or "subject to." Highlight that whole paragraph, or the sentence plus the one before and after it, so the AI has enough context. If the document is on paper, retype that one paragraph into your phone's notes app. If it's a PDF or a web page, you can usually press and hold with your finger, or right-click with your mouse, to copy the text.

You'll know it worked when you have a clean block of text ready to paste, with no private details like your full name, address, account number or signature line included.

Open any AI assistant in a new chat

Open the AI assistant you've signed up for — usually a website like chatgpt.com, gemini.google.com, claude.ai, copilot.microsoft.com, or the matching phone app. If you're not signed in, log in or sign up with your email; the basic chat is free on all of them. Tap "New chat" or look for a button near the top-left that starts a fresh conversation. The chat box is usually a wide text field near the bottom of the screen, with a blinking cursor.

If you don't see "New chat," look for a pencil icon, a plus sign, or a "Compose" button instead — every app puts it somewhere slightly different. On a phone, you may need to tap your profile picture first, then choose "New chat" from the menu that slides up.

You'll know it worked when you see an empty message box and the assistant either greets you or shows a blank screen with a blinking cursor, ready for your first message.

Paste the clause and ask for a plain-English explanation

Tap inside the message box and paste your paragraph — long-press on a phone, or Ctrl+V on Windows / Cmd+V on a Mac. Then type a short instruction right after it (or on a new line below). The instruction tells the assistant how to answer. Press Enter or tap the send arrow, then wait a few seconds. The assistant will reply with a plain-language version of what that clause actually means.

If the reply is too short or still sounds like a lawyer, don't worry — you'll sharpen it in the next step. If one assistant refuses to help or gives a strange answer, just try a different one. This kind of task is well within what all major assistants handle.

You'll know it worked when you get back 2–5 sentences that sound like a normal person talking — not a courtroom.

Ask what you're really agreeing to — and what to worry about

Stay in the same chat and type one or two sharper follow-up questions. AI assistants remember the conversation, so you don't have to paste the clause again. Push the assistant to point out the obligations, deadlines, money, and anything that could surprise you later. The more specific your question, the more useful the answer.

If the reply feels too general, push for a concrete example ("for example, what would count as 'structural damage'?") or ask for a one-sentence summary. If the assistant hedges a lot — "it depends," "you should consult a lawyer" — that's actually a good sign. It means the clause is genuinely tricky, and you've found the part worth a closer look.

You'll know it worked when you can list 2–3 specific things the contract is asking you to do, each starting with "you'll have to" or "the other side can" — not vague generalities like "this clause covers responsibilities."

Ask "what questions should I ask before I sign?"

One last prompt: ask the assistant to put itself in your shoes and come up with questions YOU should bring to the other party — the landlord, the seller, the service provider, or your own lawyer. This is where assistants earn their keep, because they've read thousands of contracts and know what people forget to ask. If the list is long, ask it to group by topic or pick the most important ones.

If the questions feel too generic, add a sentence about your situation. A first apartment, a freelance gig, and a used-car purchase all have very different gotchas, and a quick context line makes the answer much sharper.

You'll know it worked when you have a short list of questions you would not have thought of on your own, and at least one of them makes you go back and re-read the contract a second time.