When to Actually Hire a Lawyer for Your Arrangement
Most casual arrangements don't need a lawyer. A conversation, some written expectations, and mutual good faith will carry you through. But there are specific situations where spending a few hundred dollars on professional legal advice could save you thousands — or protect you from serious consequences.
Here's how to know the difference.
You Probably Don't Need a Lawyer If...
Let's start with the majority of situations where legal advice isn't necessary:
- Your arrangement is straightforward. Two people, clear expectations, modest financial involvement, and both people are happy with the terms.
- No one is giving up anything major. Neither person is quitting a job, moving cities, or making life-altering decisions based on the arrangement.
- The financial amounts are small relative to both people's income. A few hundred dollars a month in gifts or dinners is unlikely to warrant legal fees.
- Both people are on equal footing. Similar ages, similar levels of power and resources, and both people had input into the terms.
- You're just looking for a template. A written agreement that captures your mutual understanding doesn't require a lawyer to draft. Understanding what makes agreements enforceable is helpful background, but you don't need to hire someone for it.
You Should Strongly Consider a Lawyer If...
1. Significant Money Is Involved
If the arrangement involves monthly transfers of $5,000 or more, large gifts (jewelry, vehicles, tuition), or ongoing financial commitments, the stakes are high enough to warrant professional advice.
Why it matters: Large financial transfers can have tax implications, may affect divorce proceedings if either party is married, and create disputes that are expensive to resolve after the fact.
What to ask the lawyer: "How should these transfers be structured? What are the tax implications? How do I protect myself if the arrangement ends?"
2. Real Property Is Part of the Deal
If someone is being added to a lease, given use of a property, or promised a home or condo, a lawyer should be involved.
Why it matters: Property laws are complex and vary significantly by jurisdiction. Verbal promises about property are particularly dangerous because they're hard to prove and may not be enforceable without a written agreement that meets specific legal requirements.
What to ask the lawyer: "What are my rights to this property? What happens to my housing if the arrangement ends? Should this be a separate legal agreement?"
3. One Person Is Giving Up Employment or Career Opportunities
If someone is leaving a job, declining a promotion, or relocating for the arrangement, the personal sacrifice is enormous and deserves legal protection.
Why it matters: If the arrangement ends unexpectedly, the person who gave up their career is left without income and possibly without the arrangement's financial support. Without a legal safety net, they're extremely vulnerable.
What to ask the lawyer: "Can we create an enforceable agreement that provides a transition period or severance if the arrangement ends? What would that look like?"
4. Children or Custody Are Even Remotely Involved
If either person has children, and the arrangement could affect custody, child support, or a co-parenting dynamic, get legal advice immediately.
Why it matters: Family courts prioritize children's wellbeing, and a casual arrangement that affects a custody situation can have serious legal consequences for the parent involved.
What to ask the lawyer: "Could this arrangement affect my custody agreement? What should I disclose? What risks am I taking?"
5. You're Being Asked to Sign Something You Don't Fully Understand
If the other person presents a written agreement with legal language, penalty clauses, or terms you can't parse, don't sign it until a lawyer has reviewed it.
Why it matters: Some agreements contain unconscionable terms that are designed to benefit one person at the other's expense. A lawyer can identify these in minutes.
What to ask the lawyer: "Is this agreement fair? Are there terms that could harm me? What would you change?"
6. Either Party Is a Public Figure or High-Net-Worth Individual
If discretion is especially important because of one person's professional reputation or wealth, the confidentiality aspects of the arrangement may warrant formal legal structuring.
Why it matters: Confidentiality clauses in casual agreements have limited enforceability. A lawyer can draft a standalone NDA with stronger protections.
7. Something Has Gone Wrong
If the arrangement has already ended badly — threats, financial disputes, breach of privacy, harassment — a lawyer is no longer optional.
When to act immediately:
- The other person is threatening to share intimate photos or private information
- There are disputes over money or property worth more than a few thousand dollars
- You're being harassed or stalked after the arrangement ended
- You've received legal threats or a demand letter
How to Find the Right Lawyer
Not every lawyer is the right fit. Here's what to look for:
Type of Lawyer
- Family law attorney for situations involving marriage, divorce, custody, or cohabitation
- Contract attorney for reviewing or drafting specific agreements
- Privacy attorney for confidentiality concerns, intimate image threats, or reputation issues
- General practice attorney for initial consultations when you're not sure what you need
Qualities to Look For
- Non-judgmental approach. You need someone who will give practical advice without moralizing about your personal life.
- Experience with unconventional arrangements. Lawyers who handle prenuptial agreements, cohabitation agreements, or entertainment contracts are often a good fit.
- Clear communication. If the lawyer talks in jargon and can't explain things plainly, find another one.
- Transparent pricing. Ask about fees upfront. Many lawyers offer a fixed-fee initial consultation ($150-$500) where you can get answers to your core questions.
How to Have the Initial Conversation
Be honest and specific. Lawyers are bound by attorney-client privilege — they cannot share what you tell them, even if you don't end up hiring them.
Prepare:
- A brief summary of the arrangement
- The specific question or concern you need addressed
- Any documents or written communications related to the issue
- Your budget for legal services
What a Lawyer Can and Can't Do
A lawyer can:
- Review an agreement and identify problematic terms
- Draft enforceable provisions (like a standalone NDA)
- Advise on tax implications of financial transfers
- Help you understand your rights in a dispute
- Send a cease-and-desist letter if the other person is threatening you
- Represent you if things escalate to litigation
A lawyer can't:
- Make your casual arrangement a fully enforceable contract (see why)
- Guarantee any outcome
- Give you therapy or emotional support (they can refer you to someone who can)
- Undo decisions you've already made
The Cost Question
Legal advice costs money, and people in casual arrangements often hesitate to spend it. Here's a framework:
- If the arrangement involves less than $5,000 total: Legal advice probably costs more than it's worth. Focus on clear communication and written expectations.
- If the arrangement involves $5,000-$50,000: A one-time consultation ($200-$500) is worthwhile.
- If the arrangement involves over $50,000: Ongoing legal support may be warranted. Budget for it.
- If things have gone wrong: The cost of legal advice is almost always less than the cost of the problem it prevents.
The Bottom Line
Most people in casual arrangements will never need a lawyer. But knowing when you do — and acting on it promptly — can save you from financial loss, privacy violations, and emotional devastation. When in doubt, a single consultation is a small investment in a big peace of mind.
For more on the legal side of casual arrangements, explore our Enforceability Basics hub.
Disclaimer: This article provides general information to help you decide when legal advice may be warranted. It is not itself legal advice. Attorney-client relationships are formed through direct engagement with a licensed attorney in your jurisdiction.