Episode Description - Think Using AI in Divorce Daves Money? Think Again
If you've ever thought about using AI in your divorce to save money on legal fees, this podcast episode might drastically change the way you do it. Family law attorney Hillary Moonay, who co-chairs the Family Law Group at Obermeyer Rebman Maxwell & Hippol LLP and has spent 30 years in the trenches of Pennsylvania family law, shares the hidden risks AI poses in divorce cases, especially to clients who accidentally don’t use it well.
From privacy concerns to unintended legal consequences, Hillary explains where AI can create risks that most people never see coming. For example, uploading a custody evaluation to ChatGPT could expose your children to fraud. Using an AI bot to analyze what your attorney told you can dissolve your attorney-client privilege. Having AI draft your legal documents can produce legal garbage and end up costing you MORE than if you hadn’t used it at all.
Hillary breaks down the difference between using AI as a helpful organizational tool versus relying on it to make legal decisions, while highlighting the hidden details and nuances that generic AI-generated documents often miss.
If you're navigating divorce and trying to be smart about costs, this conversation offers a much clearer picture of where AI helps, where it hurts, and what questions to ask.
Show Notes
About Hillary
Hillary Moonay co-chairs Obermayer’s Family Law Group and manages the firm's Bucks County office. Her practice focuses exclusively on family law, all phases of the negotiation and litigation of domestic relations cases, including divorce, child custody, child support, alimony/spousal support, equitable distribution, prenuptial and postnuptial agreements, mediation, arbitration, and related issues. Moonay is the Past Chair of the PBA’s Family Law Section and serves on the Board of Managers for the AAML’s Pennsylvania Chapter. She also serves on the Domestic Relations Law Advisory Committee of the Joint State Government Commission, the bipartisan research agency of the Pennsylvania General Assembly.
Connect with Hillary
You can connect with Hillary through her LinkedIn page or through Obermayer's website at www.obermayer.com.
Key Takeaways From This Episode with Hillary Moonay
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Transcript
Think AI Saves Money in Divorce? Think Again
SPEAKERS
Karen Covy, Hillary Moonay
Karen Covy (00:10):
Hello and welcome to Off the Fence, a podcast where we deconstruct difficult decision-making so we can discover what keeps us stuck, and more importantly, how we can get unstuck and start making even tough decisions with confidence. I'm your host, Karen Covy, a former divorce lawyer, mediator, and arbitrator turned coach, author, and entrepreneur.
Without further ado, let's get on with the show. With me today, I have the privilege of speaking with Hillary Moonay. Hillary co-chairs the Family Law Group at Obermayer Rebman Maxwell & Hippel LLP and manages the firm's Bucks County, Pennsylvania office. Her practice focuses exclusively on family law, including divorce, child custody, child support, alimony and spousal support, equitable distribution, pre- and postnuptial agreements, mediation, arbitration, and related issues. Hillary is the past chair of the PBA's family law section, and she serves on the board of managers for the AAML's Pennsylvania chapter. She also serves on the Domestic Relations Law Advisory Committee of the Joint State Government Commission, which is the bipartisan research agency of the Pennsylvania General Assembly.
Hillary, welcome to the show.
Hillary Moonay (01:38):
Thanks, Karen. Nice to see you.
Karen Covy (01:40):
I am so thrilled to be having this conversation. This is the hot topic of the day, I have to tell you, and I'm sure you know that. I like to start when I'm talking to people by asking how they got into family law. But in your case, I'd like to know not just how you got into family law, but how you got interested in AI.
Hillary Moonay (01:54):
I actually started family law in law school. I was part of a family law clinic at the University of Michigan. We were very fortunate to have clinics where you work on actual cases. I loved it from the start and began doing some regular litigation. I am grateful that I fell into the family law group at Obermayer, which was really small. I started at Obermayer as a summer associate, came back, left for a few years, and now I've been back for a while.
Our family group at Obermayer basically started with two partners and one associate. When that associate left, I asked to jump in because I knew what I wanted to do. Now, our family law department has grown to over 20 attorneys, and we span the region, which is great.
As far as AI, it was a matter of either I get in and learn about it or I fall behind. I feel like AI came at us fast and furious. There was a bit of a trickle where you heard mentions of it, and then all of a sudden, here we are.
Karen Covy (03:09):
Bam. It was a big moment. ChatGPT hit the scene and it was all anybody could talk about.
Hillary Moonay (03:15):
Yes. You had ChatGPT and people played around with that. Really, over the last year in particular, it has grown exponentially. In addition to basic ChatGPT, you now have legal services. You have Copilot on Microsoft and Protege on Lexis. Those are the ones we primarily use and that I'm most familiar with. Our firm has a very specific AI policy, and I imagine other firms do or will soon as well.
Karen Covy (03:51):
Talk to me about that. When you say you have an AI policy, what does that mean?
Hillary Moonay (03:58):
Sure. Our policy first outlines what AI platforms we can use. We can only use closed platforms, which is why we're using Copilot and Protege. Uploading client information into the world is essentially not a good thing.
To give a quick example, we had a client who took his custody evaluation and put it into ChatGPT. Our reaction was, "Oh my goodness, you realize you just put all that information out into the world." A lot of it is confidential and privileged. But he's a client; he's not a lawyer. Now, we also had an opposing lawyer tell a judge that he ran the evaluation through ChatGPT as well. The judge was quite honestly appalled. Having these policies in place making sure attorneys follow them is a way to keep confidential information confidential and protect privacy. Also, as part of our policy, you have to check all of your work. You cannot blindly rely on AI because we've seen attorneys get sanctioned for that.
Karen Covy (05:32):
There's so much to unpack there. If I understand how this went down, did the lawyer take the fall for the client?
Hillary Moonay (05:40):
No, those were actually two different things. Our client put the evaluation through ChatGPT, which we knew because he sent it to us. We'll get to the problems with clients doing that separate from the privacy issues a little later.
The other incident involved an opposing attorney telling the judge that he put the evaluation into ChatGPT. I don't even recall why he told the judge he did it, but he said, "Well, when I put it into chat..." and we were all like, "Wait, what?" This was totally unrelated to our client. He didn't even realize that what he was saying was raising eyebrows from both our side and the judge.
Karen Covy (06:22):
Let's dive into this because this is an area that every lawyer I've ever spoken to about AI instantly recognizes, yet almost no client even thinks about: confidentiality and privilege. To start, we all know there's attorney-client privilege. If a client is talking to a lawyer, everything said between them stays between them. How does using AI affect that privilege?
Hillary Moonay (06:59):
I think that can be a major issue. We haven't seen a ton of it yet, but I'm waiting for arguments to start that information is no longer privileged because it was put into an open AI platform. For instance, a client could testify, "Well, I looked at the evaluation on ChatGPT and saw this mental health diagnosis." I am waiting for an opposing counsel to argue that none of that information is confidential anymore. I haven't seen much of that yet, but it's also hard to warn our clients about it because they don't always listen, or they do these things before we even think to caution them.
Karen Covy (07:42):
They do it before they even ask you. For people listening, just to make sure they're tracking the conversation: attorney-client privilege only extends to things you say to your attorney and your attorney says to you. If you take that conversation—whether it's a voice recording, a written transcript, or whatever—and upload it to an open platform like ChatGPT, you are uploading it to the world and breaking that privilege. Now, all of a sudden, things your opponent could not have seen or discovered before are potentially in their hands.
I was speaking with a bunch of local attorneys here in Illinois the other day, and we were talking about exactly the same thing. This technology hasn't been around long enough for these issues to make their way up through the trial and appellate courts to get definitive rulings. But once we do, you could find out that everything you thought was confidential is not confidential at all anymore, which is really scary.
Hillary Moonay (09:12):
That could be a massive problem.
Karen Covy (09:14):
Plus, explain to people the ramifications of uploading a custody evaluation that contains your children's names, birth dates, conversations, and sensitive information. What happens when you upload something like that to an open AI tool?
Hillary Moonay (09:18):
It puts it out there, and you don't know if the next person searching is going to stumble upon it. You are putting your kids' names and birth dates out there, which opens them up to regular, run-of-the-mill identity fraud because someone now has their name, birth date, and perhaps where they live.
I also worry from an emotional health perspective regarding what the kids might later find or see. What is being put out on the internet that may later be discovered about them? Maybe they have a certain diagnosis or behavioral issues. All of this is usually included in a custody evaluation, so you never know how that's going to show up later and affect your child.
Karen Covy (10:11):
A custody evaluation is usually conducted by a mental health professional, correct?
Hillary Moonay (10:21):
Correct.
Karen Covy (10:22):
And it may include psychological testing information as well.
Hillary Moonay (10:25):
Yes. It can contain sensitive history regarding both parents. Maybe you had a mental health history, a criminal history, or things you didn't really want to publicize to the world, and now you're putting that all out there too.
Karen Covy (10:41):
That's crazy. I know some firms have started adding an AI disclaimer to their client agreements, essentially telling them "don't do this with AI" because people just don't know.
Hillary Moonay (10:59):
Yes, we've talked about that. It's funny because we keep adding things to our agreement letters; they are up to five pages now. At some point, with all the things we feel we need to include to protect clients from themselves sometimes, there's just more that has to be written in.
Karen Covy (11:17):
Lawyers get a bad rap because people complain about a 5- or 10-page agreement. That's true, but there are so many things lawyers are trying to protect their clients from, which is what makes the agreement read like War and Peace.
Hillary Moonay (11:34):
Yes, 100%.
Hillary Moonay (11:39):
I told a client yesterday that my job is to advocate for her, advise her, and protect her legally, and that might not always mean what she wants it to mean.
Karen Covy (11:49):
Tell me about that.
Hillary Moonay (11:51):
We were having a discussion after a mediation session. She said, "I didn't feel like you were supporting me." I told her, "What me supporting you looks like may be different from your perspective. Me supporting you is making sure I'm protecting you legally, advising you properly, and advocating for you properly. I am reading a room differently than you might be reading it. When I tell you that's enough and to stop talking, it's not because I'm not supporting you—it's because I'm doing my job." Sometimes that's what we have to do, and people don't always want to hear it.
Karen Covy (12:26):
I remember as a young lawyer back in the day, I was arguing a case in front of a judge. It was a motion hearing, so it was all legal arguments with no testimony. The other side kept jumping in, going on and on, and I was chomping at the bit to interrupt and say my piece. The judge was just listening to them, and it was almost like the judge and the other lawyer were having a private conversation. Finally, I was able to butt in and said, "But Your Honor, blah, blah, blah..." The judge just looked down at me and said, "Counsel, when you're winning, it's often wise to keep your mouth shut."
Hillary Moonay (13:17):
That's so true. But sometimes in the moment, you just can't help it.
Karen Covy (13:24):
I learned from that moment on to keep my mouth shut, but that was a lesson I had to learn even as a lawyer. A client doesn't know that they are often shooting themselves in the foot.
Hillary Moonay (13:34):
That was exactly the conversation we had. I said, "Look, I am always supporting you, it's just that I'm doing it the way I see best." To her credit, after that, she said, "Okay, I understand now. I just didn't know why, and I wanted to understand." I told her that was perfectly fine and she can ask anything she wants. But that's why we do certain things.
Karen Covy (13:56):
Speaking of asking, a lot of clients these days are asking AI chatbots for legal advice, saying, "Here's my case and situation, what should I do?" Or my favorite: "Can you draft me a settlement agreement or a parenting agreement?" I see you putting your hand over your face. Talk to me about that. Tell clients what you wish you could tell them when they're sitting there.
Hillary Moonay (14:26):
I understand that clients aren't familiar with family law. They haven't been eating, breathing, and sleeping this for the last 30 years like I have. They are trying to understand, help, and educate themselves, and that's great.
The first thing to know about AI is that it can only give you what you give to it. If you aren't giving it specific rules—for example, if you just say, "Draft me a custody agreement for two children with 50-50 custody"—it's not taking into account Pennsylvania-specific or Illinois-specific laws and requirements.
Secondly, it's not taking into account the specifics of your situation. The rules and prompts you give to AI are the most important thing when trying to do this. You need to tell the tool, "Please draft me a parenting agreement with 50-50 custody for children of these specific ages. The parties live 50 miles apart, one child has soccer every day after school and goes directly to lacrosse practice for the rest of the night." You need to be incredibly specific because what those platforms can't do on their own is take into account your family's unique situation.
You may have kids on different school schedules, one in public school and one in private school. They may have completely different vacations or school days. If the parents live 50 miles apart, it's not practical for 50-50 custody to look like a standard alternating week split. It may look more like one parent having all of summer vacation, winter breaks, and long weekends. You may have kids with special education or medical needs. AI platforms can't draft for that unless you tell them.
Karen Covy (16:56):
Have clients ever brought you an AI-drafted custody agreement?
Hillary Moonay (17:03):
Yes, and quite honestly, it makes me want to poke my eyes out. Even if it's just basic, without taking into account all the complex variables, it doesn't read coherently for court purposes.
For a simple example, many states use the term "parenting time." That's a very clear phrase, but we don't use that in Pennsylvania; here, it's "custodial time." Because the majority of states use the phrase "parenting time," the AI will generate something using that term. Certain states, like Texas, have very specific custody template rules. If the AI is pulling from something like that, it makes no sense here.
Ultimately, it takes more work for me to fix it. I could write a proper Pennsylvania custody agreement or stipulation much more efficiently and cost-effectively from scratch than trying to revise something that makes no sense and is likely missing crucial items.
Karen Covy (18:28):
That is so important, and I really hope people hear you say that. People use AI for many reasons—one is for their own understanding, but another is because AI is free and their lawyer charges hundreds of dollars an hour. What I hear you saying is that using AI to generate a document and bringing it to a lawyer actually costs them more.
Hillary Moonay (19:00):
It often does. I have a client who likes to send me AI-generated memos on lots of different topics. He will freely admit they are generated with AI, but they can be seven pages long and I have to comb through them for a single piece of information. Sometimes there is just nothing in there that helps me because it's too dense.
I would much rather you send me a bulleted list of the things you think are important. We can faster and more efficiently either have a conversation, respond via email, or put it into a proper document you can use for court. It's a much better use of their time and money.
I am okay with AI for certain things, though. For example, if a client is coming in for the first time and they ask a chatbot, "What questions should I ask a potential divorce attorney during a consultation?" That's great because it helps them start thinking about things, and then we can have a productive conversation. It also does a good job of organizing financial information if you feed it the right data.
One of my colleagues mentioned on our department call this morning that she uploaded custody factors to Copilot. We have specific custody factors in Pennsylvania, as do many states. She then uploaded a court transcript and asked Copilot to pull out testimony that supported each factor. She said it did a pretty good job. Even as lawyers, we are using it to cut down on billable time. We aren't going through transcripts line by line initially; we use AI to start. It can be cost-effective if both the lawyer and the client use it the right way.
Karen Covy (20:47):
And to remind people of what you said earlier, you are using Copilot within a closed system. The information uploaded from a transcript or potential custody agreement stays within the law firm environment; it doesn't go out into the public ether. It stays confidential and privileged.
Karen Covy (21:19):
You mentioned organizing data. In a lot of divorce cases, there are questions about financial spending. Clients want to know what a spouse has really been spending money on, if there is a new significant other, or if there are expenses that should be flagged. Is it okay for a client to upload a credit card statement and ask AI to organize it into categories or flag unusual items? Or should they black out certain information first?
Hillary Moonay (22:02):
They should absolutely redact or black out certain information first: any names, addresses, and account numbers. To some extent, I even tell clients to blank out the specific total amounts if they are wealthy and spend a lot of money on their cards, just because I am super sensitive about what information is put out there.
Once AI helps you organize it into categories like food or travel, you can always go back to your original statement and cross-reference the amounts. For sorting and organizing data, AI is super helpful. It can help clear up assumptions; sometimes parties think certain suspicious things are going on, but when you look through the sorted categories you realize, "Okay, this is just how we live, we just spend a lot on food." Alternatively, if you didn't travel but your spouse's credit card categories show thousands of dollars in travel, it piques your interest and lets us know we need to look into that further.
Karen Covy (23:18):
AI is good for figuring out what questions to ask a lawyer, and it's good at sorting, organizing, and analyzing financial data like credit card statements. What else is AI good at for a client?
Hillary Moonay (23:36):
It can help organize their thoughts. If a client is reading through a legal memo I've drafted, it may contain heavy legal terminology. It's helpful for clients to ask AI, "Simplify this for me. What do these cases actually say?" When we write briefs or memos for the court, we use legalese, which may not be as clear to a layperson. AI helps drill it down so clients don't get caught up in the complex legal language.
I have also told clients it can be good for things like deposition, direct exam, or cross-examination prep. Not for the exact case specifics, but if you want to ask an internal tool like Copilot, "I had an affair during my marriage and I'm afraid this is going to affect my alimony. I'm going to be cross-examined on this, what questions should I expect?" It will throw out basic questions to help prepare you. Your lawyer should always be preparing you for that, but it helps you see the general areas of focus. If it surfaces something your lawyer hadn't brought up yet, you can bring it to them and ask how to handle it.
Karen Covy (25:26):
We've talked about how clients use AI. Talk to me a little bit about how judges feel about it and what they are expressing from the bench.
Hillary Moonay (25:35):
I think judges can generally tell when something is written by AI. I almost always can. There are certain giveaways, like AI using a lot of dashes. It seems silly, but it's a stylistic thing; I don't write with dashes, and it's not typically what you see in formal legal memos and briefs.
The biggest issue for judges regarding AI is discerning what is true and what is not. Take protection from abuse matters, for example. Judges are increasingly concerned about whether evidence is AI-generated. Were these text messages actual exchanges between the parties, or were they fabricated by AI?
Karen Covy (26:38):
Thinking like a lawyer, that would be an absolute nightmare.
Hillary Moonay (26:43):
As lawyers, we rely on our clients to provide us with the information we use to litigate. It used to be much harder to manipulate evidence, but it's not so hard right now. What if someone takes a text string, puts it into an AI tool, and prompts, "Here is our text string, modify it to make it sound like he was more violent toward me"? It outputs a realistic-looking printout. People can do all sorts of things now, including changing pictures. We've seen it all over the place.
Judges worry deeply about the validity of the information they are receiving. We have also seen issues with AI "hallucinating" cases. Every attorney ethically must check every single case—putting eyes on the specific case name and citation—before it goes into any submission to the court.
Karen Covy (27:53):
To our earlier point, as a lawyer, you now have to look up every single case that either you or your opponent cites for anything. Back in the day, you knew certain benchmark cases and what they said, and you'd only look it up if something sounded unusual. It's not just a question of whether a case exists, but whether it actually says what the AI claims it says.
Hillary Moonay (28:34):
That's the bigger piece of it. Even if the case exists, it may not say anything close to what the AI decided it says.
We had a really fun program at the AAML (American Academy of Matrimonial Lawyers), which is based in Chicago. Our Pennsylvania chapter had an AI retreat in the fall. A professor came in to talk to us about AI, and our chair split us into teams for a Jeopardy-style game with questions put up on the screen. We didn't know what she was doing; we just thought it was a standard family law trivia game.
All of a sudden, these completely unfamiliar cases would pop up. The screen would say a case stood for a proposition like, "Alimony isn't awarded when someone has had an affair"—which isn't even true. We were all looking around saying, "None of us have ever heard of this case, this is so weird." The twist at the end was that the entire game was completely AI-generated. We were all blown away. It finally made sense, and that's when it clicked for all of us: holy cow, this is a real problem. It was outputting legal propositions that made zero sense.
Karen Covy (30:12):
That's crazy. The troubling thing about AI is that whatever it says, it says with gusto and 100% confidence, so you assume it must be true.
Karen Covy (30:30):
What about the things AI leaves out? As a lawyer, you know what is supposed to be in a document, but how can a client spot omissions?
Hillary Moonay (30:41):
They can't, and that's why it's so hard when clients have agreements drafted independently. They will come in and say, "My husband and I signed this agreement that we had AI draft." You look at it and realize there is no real financial disclosure included, and there is no waiver of financial disclosure. In order for a marital settlement agreement to be valid, full disclosure is a strict requirement. If it's not there, the agreement can be completely overturned later because they didn't know what they didn't know.
Karen Covy (31:13):
Let me play devil's advocate here. If I'm the client bringing you this document, saying, "Well, we did this and we thought it was good enough. What's the harm?"
Hillary Moonay (31:24):
The harm is that a year from now, if your spouse decides that the trust or inheritance you had—which might be three times the size of your marital estate—wasn't properly disclosed, they are going to come back, try to overturn the agreement, and drag you back to square one.
Karen Covy (31:45):
The challenge is that you don't know if the agreement AI wrote for you is good or bad until you actually need it to be good, and by then it's too late to change it.
Hillary Moonay (31:57):
Exactly. Years down the road, a spouse comes back and says, "We divided our small estate 50-50 and went our merry ways, but now my ex-wife is traveling the world and taking the kids on exotic vacations. I don't know how she's doing this because we never had that kind of money." It turns out she received an inheritance during the marriage that may or may not have been marital property, but because it wasn't disclosed, it could have a major effect on how the marital estate should have been divided.
Karen Covy (32:30):
If people take anything away from this, it's that family law is deeply nuanced. Yes, there are written statutes and cases, but how that law is interpreted and applied is incredibly specific. At least as of 2026, I don't think AI can replace a lawyer yet.
Hillary Moonay (32:58):
Not yet. I know clients are trying to keep costs down, and that's a big reason why they use it. But there are other ways to keep costs down and still have it done right. Mediation can be incredibly cost-effective.
I have a client right now where she and her spouse agreed on all the terms themselves. They both have attorneys, but they worked out the core terms on their own. However, I am drafting the actual agreement and reviewing it with the opposing attorney. Because of that, I can go back to the clients and point out what's missing.
To give you an example, their notes said my client, the wife, was going to decide whether or not to keep a car, and she had until the end of August 2026 to make the choice. Based on the timeline of everything else, they are going to be legally divorced by then. I told her, "That's fine, but if you decide to keep it and the title has to be transferred to you after you are already divorced, you will have to pay transfer taxes on that vehicle because you are no longer married. If we do it ahead of time while you are still married, you don't pay a transfer tax." It could be a lot of money or a little money, but there was no way for her to know that on her own. So, we moved the decision date up so the vehicle transfer happens prior to the divorce decree.
Those are the little things clients won't know. You can still work with your spouse to come up with the basic terms of an agreement—perhaps even using AI to brainstorm ideas of what is fair—but then you must go to your attorney to dot the i's and cross the t's.
Karen Covy (34:54):
And to draft the actual documents. People still come to me for consultations bringing these AI-generated documents, and I have never seen one that would fly. It is always harder to fix those.
Hillary Moonay (35:12):
It is honestly harder to fix them. I would much rather start with what I know is a solid base where nothing is missing, rather than try to patch up an AI agreement.
Karen Covy (35:22):
Because you know what you want to see in every agreement, and it's already built into your proven templates. With an AI document, you have to meticulously search through what they've given you to see if a specific clause or paragraph is there, and that takes much longer.
Hillary Moonay (35:42):
Yes, and it can also completely miss assets. There may be financial components that parties don't think to ask about. They might assume, "Well, that asset was his from before we got married, so we didn't include it." I have to tell the client, "That's fine, but you were married for 30 years. In Pennsylvania, the increase in value of that premarital asset during the marriage is considered marital property. It's fine if you want to waive your right to it, but you don't know what you don't know."
AI tools can only give you information based on the exact prompts you feed them. If you don't tell the AI that there is a premarital 401(k) that has been growing untouched for 30 years while you've been married, it won't include it in the agreement because it doesn't know it exists.
Karen Covy (36:36):
Hillary, this has been such a helpful conversation. I wish I could put this out on loudspeakers and shout it from the hilltops.
Hillary Moonay (36:46):
Me too, Karen.
Karen Covy (36:50):
If people are interested in learning more or want to work with you—because clearly, you know your stuff—where can they find you? What is the best place?
Hillary Moonay (36:59):
The best place is our website, obermayer.com (O-B-E-R-M-A-Y-E-R.com). My profile is on there with all of my contact information.
Karen Covy (37:11):
For anyone listening, we will link to everything in the show notes. Hillary, thank you so much. I really appreciate you sharing your expertise.
Hillary Moonay (37:21):
It was so nice chatting with you, Karen. This was fun.
Karen Covy (37:24):
For those of you watching or listening, if you enjoyed today's conversation and want to hear more just like it, do me a big favor: give the episode a thumbs up, like and subscribe to the podcast, subscribe to the YouTube channel, and I look forward to seeing you all again next time.
