

How Not To Suck At Divorce: Divorce Advice and Relatable Humor
Morgan Stogsdill and Andrea Rappaport
How Not to Suck at Divorce guides anyone who’s divorcing or even just considering divorce. Hosted by Morgan Stogsdill and Andrea Rappaport, the show delivers equal parts strategy, empathy, and humor.
Morgan Stogsdill is a powerhouse family law attorney and head of family law at the largest firm in the United States. She’s seen every curveball, knows the difference between drama and strategy, and helps clients avoid costly mistakes. Andrea Rappaport is a comedian, marketing pro, and divorced-then-happily-remarried mom who has made the exact painful mistakes we beg you not to repeat. Together, we’ve built a podcast that blends courtroom-level insight with compassionate, practical moves you can use the second the episode ends.
Our community is loyal, our guests are leaders, and our episodes are packed with value. In short: listening to How Not to Suck at Divorce will help you avoid major divorce mistakes.
We launched this show to fill the gap between “funny but fluffy” podcasts and “useful but soul-crushing” legal jargon. The goal: actionable empathy. With scripts, checklists, and boundaries ready, you’ll make fewer panic decisions and save money, time, and sanity.
What We Cover
Should I stay or should I go? Decision-making frameworks, acronyms, and step-by-step exercises for clarity.
Co-parenting and high-conflict personalities. We unpack narcissist dynamics, manipulation tactics, and non-reactive communication. (We even created a framework called “WTF” to help you remember it when your brain is on fire.)
The BIFF method and conflict de-escalation. With Bill Eddy of the High Conflict Institute, we translate his tools into real-world texts and emails you can send without blowing up your case.
Tech safety and AI mistakes. Steven Bradley, former FBI agent and digital safety expert (“Tech Cowboy”), explains how tech evidence, AI hallucinations, and smart device trails can help—or hurt—your case.
Prenups, financial transparency, and power dynamics. Guests like Katie Post share what to include, what to avoid, and how to start the conversation before things go off the rails.
That’s our recipe: expert interviews + practical tools + humor that keeps you breathing. Episodes are short enough for a dog walk but deep enough to change your next decision.
Who You’ll Hear
We curate guests who’ve sat in every chair—lawyers, therapists, digital forensics pros, financial planners, safety advocates, and survivors who turned their mess into a roadmap.
Bill Eddy (High Conflict Institute): BIFF and EAR techniques, parallel parenting, and communication guardrails.
Steven Bradley (former FBI “Tech Cowboy”): Digital breadcrumbs, evidence handling, and how AI can backfire in divorce.
Dr. Nadine Macaluso (therapist, trauma specialist): Love-bombing, trauma bonds, and healing after divorce.
Joanna Strober (Midi Health): Resilience, perimenopause, career pivots, and financial autonomy.
Core Topics
Divorce Strategy & Family Law: prenups, mediation vs. litigation, custody agreements, relocation, settlement strategy.
High-Conflict & Safety: coercive control, gaslighting, DARVO, BIFF vs. gray-rocking, protective orders, tech hygiene.
Co-Parenting & Parallel Parenting: calendars, school/holiday schedules, and communication protocols.
Money & Power: financial disclosure, tracing assets, budgeting, and managing fees.
Mindset & Mental Health: compartmentalizing, trigger management, boundary scripts, and choosing the right therapist or coach.
Our show is both resourceful and entertaining. You’ll laugh, take notes, and walk away feeling less alone. With 160+ episodes and weekly updates, How Not to Suck at Divorce has become a trusted resource worldwide.
Whether you’re in the middle of a divorce, just considering it, or rebuilding afterward, this podcast helps you breathe easier, protect your sanity, and avoid the mistakes that cost people the most.
You’ll get through this. We promise. You’ve got this… and we’ve got you.
Morgan Stogsdill is a powerhouse family law attorney and head of family law at the largest firm in the United States. She’s seen every curveball, knows the difference between drama and strategy, and helps clients avoid costly mistakes. Andrea Rappaport is a comedian, marketing pro, and divorced-then-happily-remarried mom who has made the exact painful mistakes we beg you not to repeat. Together, we’ve built a podcast that blends courtroom-level insight with compassionate, practical moves you can use the second the episode ends.
Our community is loyal, our guests are leaders, and our episodes are packed with value. In short: listening to How Not to Suck at Divorce will help you avoid major divorce mistakes.
We launched this show to fill the gap between “funny but fluffy” podcasts and “useful but soul-crushing” legal jargon. The goal: actionable empathy. With scripts, checklists, and boundaries ready, you’ll make fewer panic decisions and save money, time, and sanity.
What We Cover
Should I stay or should I go? Decision-making frameworks, acronyms, and step-by-step exercises for clarity.
Co-parenting and high-conflict personalities. We unpack narcissist dynamics, manipulation tactics, and non-reactive communication. (We even created a framework called “WTF” to help you remember it when your brain is on fire.)
The BIFF method and conflict de-escalation. With Bill Eddy of the High Conflict Institute, we translate his tools into real-world texts and emails you can send without blowing up your case.
Tech safety and AI mistakes. Steven Bradley, former FBI agent and digital safety expert (“Tech Cowboy”), explains how tech evidence, AI hallucinations, and smart device trails can help—or hurt—your case.
Prenups, financial transparency, and power dynamics. Guests like Katie Post share what to include, what to avoid, and how to start the conversation before things go off the rails.
That’s our recipe: expert interviews + practical tools + humor that keeps you breathing. Episodes are short enough for a dog walk but deep enough to change your next decision.
Who You’ll Hear
We curate guests who’ve sat in every chair—lawyers, therapists, digital forensics pros, financial planners, safety advocates, and survivors who turned their mess into a roadmap.
Bill Eddy (High Conflict Institute): BIFF and EAR techniques, parallel parenting, and communication guardrails.
Steven Bradley (former FBI “Tech Cowboy”): Digital breadcrumbs, evidence handling, and how AI can backfire in divorce.
Dr. Nadine Macaluso (therapist, trauma specialist): Love-bombing, trauma bonds, and healing after divorce.
Joanna Strober (Midi Health): Resilience, perimenopause, career pivots, and financial autonomy.
Core Topics
Divorce Strategy & Family Law: prenups, mediation vs. litigation, custody agreements, relocation, settlement strategy.
High-Conflict & Safety: coercive control, gaslighting, DARVO, BIFF vs. gray-rocking, protective orders, tech hygiene.
Co-Parenting & Parallel Parenting: calendars, school/holiday schedules, and communication protocols.
Money & Power: financial disclosure, tracing assets, budgeting, and managing fees.
Mindset & Mental Health: compartmentalizing, trigger management, boundary scripts, and choosing the right therapist or coach.
Our show is both resourceful and entertaining. You’ll laugh, take notes, and walk away feeling less alone. With 160+ episodes and weekly updates, How Not to Suck at Divorce has become a trusted resource worldwide.
Whether you’re in the middle of a divorce, just considering it, or rebuilding afterward, this podcast helps you breathe easier, protect your sanity, and avoid the mistakes that cost people the most.
You’ll get through this. We promise. You’ve got this… and we’ve got you.
Episodes
Mentioned books

Oct 20, 2022 • 1h 2min
38. Healing From Infidelity with Dr. Randy Heller
Today we have fan favorite Dr. Randy Heller to discuss how to heal from infidelity. Betrayal often has a huge impact on the divorce process because it adds fuel to an already raging fire. We want to help you move through the anger so you can make good decisions during your divorce. This is a heavy issue but we promise, by the end of the episode, you will feel better. If you're new here, Dr. Randy Heller is a licensed marriage and family therapist, licensed mental health counselor, certified Supreme Court family mediator, credentialed collaborative divorce family specialist and facilitator, parenting coordinator, certified hypnotherapist, and the founder and Clinical Director of The Family Network. Like, wow. Dr. Randy talks about the different types of infidelity. It's not just cheating. Infidelity can also be lying, stealing, and hiding money. Infidelity can be any type of betrayal. We talk about: Triggers after the betrayal How to trust your attorney after having your trust broken by your spouse How to deal with the pain of infidelity How to heal Because levity is important, we didn't skip our obsessed segment today. This week Morgan is obsessed with Meyers hand soap. Her fave scents are Rosemary, Rain, and Daisy (it doesn't smell like flowers). Post-pandemic Morgan is especially appreciative of how well it lathers and cleans. We're not affiliated with Meyers but if they want to slide into our dms, we won't be sad. You can find Dr. Randy Heller here: thefamilynetwk@aol.com 646-717-6718 mycollaborativeteam.com No matter what you're going through, we're here for you. We love hearing from you so don't be shy. Slide into our dms: @hownottosuckatdivorce @theandrearappaport @divorceattorneychicago If you're liking our little show, it would mean the world to us if you rated and reviewed us right in your Apple podcast app or wherever you listen XO

Oct 13, 2022 • 58min
37. Putting Your Children First in the Parenting Agreement with Malissa Tigges
This is no episode for babies (no offense, babies). We're getting into some real, REAL stuff in this episode. This is one of the biggest concerns our listeners have so we wanted to dedicate an entire episode to how to put your kiddos first in your parenting agreement. Today, we have therapist Dr. Malissa Tigges with us to talk about how to create a parenting agreement that prioritizes the welfare of your kids. Dr. Tigges is a licensed clinical and forensics psychologist with over 10 years of experience working as a psychotherapist and an evaluator. She helps people make the best decisions possible when developing their parenting agreements. Dr. Tigges, Morgan and Andrea answer: What do divorcing couples need to understand when putting together their parenting agreement? How to design the parenting agreement so it's appropriate at each age of the children. The biggest mistake divorcing couples make when creating their parenting agreement. What is the main difference of a parenting plan that involves a younger child vs. a teenager? Can you modify a parenting agreement? Who should you consult with to ensure your parenting agreement is the best for your child? Should you open the parenting agreement email after having a few drinks? What is co-parenting therapy and is it necessary? What do you do when your rights are being violated during the divorce process when you're drafting the parenting agreement? What's the best schedule for co-parenting? 50/50? Week on, week off? Every other weekend? The answer may upset you, but it's important to understand. Is there wiggle room in a parenting agreement if there's a special trip or long weekend planned? Dr. Tigges also shares her absolute "must-dos". Here is where you can connect with Dr. Tigges: @drmalissatigges on instagram, tiktok and facebook Dr. Tigges is licensed in Florida but if you're not in Florida, your state may allow you to do telehealth with Dr. Tigges so if you need guidance, reach out! OBSESSED: This week Andrea is obsessed with a non-medicated inhaler that has been scientifically proven to calm anxiety. It's called CalmiGo. It measures how much air you exhale and will vibrate when you exhale properly to help you regulate your breathing. It helps Andrea feel more grounded and has made her realize how shallow she typically breathes during the day. It's genius. CalmiGo sent the inhaler to Andrea after she posted the instagram reel of the time she was in the hospital for a panic attack. But please know, we do not recommend products just because we got one free. We will only recommend products we truly love and use. And this is one of those, for sure. If you go to Andrea's IG and click the link in her bio, you'll get a $30 off coupon. Don't miss the very end of the episode because we talk about how it has just been discovered that honey bee venom can kill breast cancer cells. Amazing! There's also a new study on a possible cure for lupus and other autoimmune diseases AND, new developments on slowing the progression of Alzheimer's. We love ending the show with some positivity :) To our one listener in Honduras, we see you and adore you. Thank you for being here with us. xo We'd love to know what you think of the show! Please email us at hello@hownottosuckatdivorce.com or dm us at: @theandrearappaport @divorceattorneychicago You can also reach out to us through our website: www.hownottosuckatdivorce.com We read every message and reply personally because our community means the world to us and we want you to know we're here for you. You got this and we got you.

Oct 6, 2022 • 52min
36. Divorce and Finding Your Community with Rob Roseman
Andrea and Morgan are back with best friend of the podcast and fan fave Rob Roseman! Rob is the host of the popular podcast WTF Divorce and a single dad who felt the very common feeling of isolation when he went through his own divorce 2.5 years ago. Rob shares his story and the three discuss how to avoid isolation and find your community so you can not just survive, but thrive. Morgan, Andrea and Rob discuss: Is it helpful to find others who are going through a divorce or does that make it even more difficult? Trauma bonding during divorce. How Rob and Andrea met. How finding divorce friends is like dating. How Andrea's painful divorce and isolation led her to the podcast and our wonderful community with the absolute best listeners. Why Morgan started this podcast with Andrea and what surprised Rob about her reason. *** Be sure to listen until the end because Andrea and Morgan get real about friendships during a divorce. If you're not already listening to Rob's podcast, following him on IG, and all over his website taking advantage of all his free resources (including a search tool to find divorce attorneys and therapists in your area), we highly recommend you do so now! Here is where you can find Rob: @wtfdivorce www.wtfdivorce.com WTF Divorce Podcast If you're struggling to find your community, please reach out to us and we will be here for you. Email us at hello@hownottosuckatdivorce.com or dm us at: @theandrearappaport @divorceattorneychicago You can also reach out to us through our website: www.hownottosuckatdivorce.com By the way, we love that you love our new OBSESSED segment, because we love it too! This week Morgan is obsessed with Sand and Fog candles. If you like candles that actually do what they're supposed to, smell up your house and last, these are for you. They're pretty, smell incredible and they won't break the bank. They even have candles that are meant to clean up pet smell. This week Morgan is burning Juniper Mint, yum. She also highly recommends Clean Linen. We're not affiliated with Sand and Fog and they didn't pay us to review them...Morgan just truly adores them and wants to share the love. Sand and Fog website That's all for this week, friends. Don't forget, you got this and we got you xo.

Oct 1, 2022 • 58min
35. Tinder for Divorce Attorneys with Max Leinoff; How to Find the Right Divorce Lawyer
This week we're talking about how to find the right divorce lawyer. It's like Tinder for Attorneys! To break it all down, we have Max Leinoff on the pod. Max is a family law attorney in Miami, Florida with Leinoff and Lemos, P.A. His firm was voted one of the Best Law Firms by U.S. News and World Report for 2021 and 2022. Max answers: What three things you must hear from your divorce attorney What should you do if your divorce lawyer disagrees with you? The importance of expressing your goals honestly with your divorce lawyer Who will you be working for when you hire an attorney? Is it a bad sign if they have other associates helping you? What questions should you ask divorce lawyers before deciding who to hire? These may surprise you. What is a no fault state when it comes to divorce? How can you work with your divorce attorney to move things along swiftly and smoothly? "When you're looking for an attorney, you don't want a yes man or a yes woman." - Max Leinoff If you're in Florida, here is where you can find Max Leinoff: Max@LLPA.com www.llpa.com (305) 661-1556 - office Also, Max shouts out his lovely wife, Katy, who is an incredibly talented, professional artist who has worked with Vans and was recenly featured on the Ralph Lauren website. You can see Katy's work on instagram @katyilana. We checked her out and now we're obsessed with her, too! We had so much fun with Max, we made him participate in Spin the Wheel, Andrea's favorite segment (Morgan hates it). What embarrassing thing will Max have to do? Stay to the end to find out. Don't missed our OBSESSED segment: This week, Morgan is obsessed with Portillos. We ordered Portillos during the photoshoot for this season, because Morgan and Andrea love nothing more than a great cheeseburger. The photographer kept shooting because watching the us chow on Portillos in fancy dresses was too good to miss. If you're not from Chicago, you may not know how amazing Portillos is. They are iconic. They're best known for hot dogs, burgers and Italian beef (and cheese fries and chocolate cake shakes). If you're not in Chicago, you can have their food shipped to your door. Life-changing. We're not affiliated (yet)....we're just obsessed. We'd love to know what you think of the show! Please email us at hello@hownottosuckatdivorce.com or dm us at: @theandrearappaport @divorceattorneychicago You can also reach out to us through our website: www.hownottosuckatdivorce.com We read every message and reply personally, because our community means the world to us and we want you to know we're here for you. You got this and we got you.

Sep 22, 2022 • 1h 9min
34. The Do's and Don'ts of Divorce with Rebecca Armstrong
Oh friends, you won't want to miss this episode. Morgan and Andrea are back this week with top Dallas family law attorney, Rebecca Armstong, talking about the things you SHOULD and SHOULDN'T do after you file for divorce. Rebecca, Morgan and Andrea answer: What 3 things should you do after you file for divorce? What 3 things should you absolutely NOT do after you file for divorce? Do I need a therapist if I'm going through a divorce? Can being in therapy be used against me if I'm going through a divorce? Why should I go to an annual checkup at the doctor during a divorce? Can I record my spouse during an argument and use it during divorce proceedings? Will my spending habits be scrutinized during a divorce? What advice did Oprah give Andrea about her own divorce? Texas friends! You can reach our fabulous guest Rebecca at: www.armstronglawtexas.com 214-741-9906 As always, we love hearing from you so feel free to slide into our dms: @hownottosuckatdivorce @theandrearappaport @divorceattorneychicago You got this and we got you xo

Sep 15, 2022 • 38min
33. Divorce and Discernment Counseling with Dr. Bill Doherty
Would you benefit from Discernment Counseling? This week, we find out. The founder of discernment counseling, Dr. Bill Doherty, joins us on the podcast. Not only did Dr. Doherty develop a specific type of counseling for couples where one is considering divorce, he's also been on Oprah not just once, but twice! From Harpo to How Not To Suck At Divorce, Dr. Doherty is moving up in the world, that's for sure. Discernment counseling is when one person is leaning OUT of the relationship and considering divorce and the other person is leaning IN and wants to try to make things work. This type of counseling gives people clarity and confidence based on a deeper understanding of what has happened in the marriage. Dr. Doherty answers the questions: What is discernment counseling? Does discernment counseling solve problems in the marriage? What are the differences between couples therapy and discernment counseling? How long is discernment counseling? What are the three paths of discernment counseling? How do I know if we should try couples therapy or discernment counseling? Stay until the end because Dr. Doherty blows the lid off traditional therapy and tells us he favorite type of wine (you won't believe his answer). You can find Dr. Bill Doherty and search for a local discernment counselor at discernmentcounselors.com. Please hit the 5 stars in your podcast app, we need the external validation, but more importantly, it helps our podcast show up in searches so we can help those who are struggling through the divorce process. Remember, you got this and we got you. Slide into our dms, we love hearing from you! @theandrearappaport @divorceattorneychicago

Sep 8, 2022 • 37min
32. Divorce Prenups with Katie Post
Divorce and prenuptial agreements go together like champagne and charcuterie. The prenup queen Katie Post joins us. Katie is a family law attorney, like Morgan, and an expert on prenup agreements. Prenups can play a huge role in divorce settlements. But they are often a total mystery so we decided to break it all down for you. Katie answers: What are the three things EVERYONE needs to know about their prenuptial agreement? Should I get a prenup? Do I qualify for a prenup? Is it true only wealthy people get prenups? Does getting a prenup make me a gold digger? What does a prenup cover? Can a prenup impact my business? What is maintenance? How can I get a prenup thrown out? We'll also discuss the one huge mistake you should not make when writing up your prenup, divorce and prenup law in Illinois and other states, and the type of attorney you should use to draw up a prenup. Also, Andrea will share some wild prenup stories. Be sure to stay until the end for a really sweet story that will make your day. You can find the Prenup Queen, Katie Post, here: kpost@beermannlaw.com You can also contact Katie at 312-621-9700 As always, we love hearing from you! Slide into our dms with questions, comments, grievances or love here: Morgan on IG @divorceattorneychicago Andrea on IG @theandrearappaport And don't forget to follow our show's new IG for more tips and divorce humor: @hownottosuckatdivorce You got this and we got you xoxo Please tag us on social, and send us your fave photos of Kanye West!

Sep 1, 2022 • 28min
31. Divorce and Alcohol Addiction with Soberlink's Chris Beck
Today we're talking about divorce when alcohol addiction is involved, with Soberlink's Chris Beck. Alcohol addiction is on the rise and it can exacerbate the already difficult process of divorce. We know how delicate and important this issue is so we want to remove the stigma and speak openly about how it impacts both parties and how to make navigating divorce with alcohol addiction a little easier. We talk about a device called Soberlink that Morgan has been using for several years in her family law practice. Soberlink combines a breathalyzer with facial recognition software and wireless connectivity to produce a confirmation report of sobriety that can be sent to anyone who is a part of the monitoring agreement (lawyers, coparent, rehab facilities, etc). This reduces conflict and gives the coparent assurance that their child is being cared for by a sober parent. It also gives the parent with the alcohol addition the opportunity to be in their child's life. It's truly a wonderful device for all involved. We loved our conversation with Chris because it's so clear how much he cares about keeping families together during divorce when one person struggles with alcohol addiction. Keeping families together during and after divorce is our mission as well so his words really resonated with us. Plus Chris made us laugh, and he made Andrea cry so it's very well-rounded just as we like it. Thank you, Chris! Tap here to go to soberlink.com to learn more about their tech, programs and examples of family law orders. You can also check out soberlink on: Twitter @soberlink Facebook @soberlink We'd love to hear from you! Are you divorcing someone with an alcohol addiction? Do you have an alcohol addiction and you're worried how it will play out? Have you used Soberlink? @hownottosuckatdivorce @theandrearappaport @divorceattorneychicago Remember, you got this and we got you.

Aug 25, 2022 • 47min
30. Is It My Marriage That's Making Me Miserable? with Dr. Randy Heller
Listener fave Dr. Randy Heller is back with us today to discuss one of the most common questions we get: Is it my marriage that's making me miserable? Dr. Heller shares what people should do if they're feeling depressed, stressed and overwhelmed and an easy exercise to do to determine if it's the marriage that is the root of the problem. We also talk about how to start to feel better, regardless of the decision we make in our marriage. You can find Dr. Randy Heller here: thefamilynetwk@aol.com 646-717-6718 mycollaborativeteam.com No matter what you decide, you got this and we got you. We love hearing from you so don't be shy. Slide into our dms: @theandrearappaport @divorceattorneychicago

Aug 18, 2022 • 43min
29. When I Knew It Was Over with Mike Draper
We're back with Season 3! We thought we'd kick off the best season yet by starting at the beginning of the end . . . when you know it's over. We welcome guest and retired husband Mike Draper to the show as he shares his story of when he knew it was over and what life after divorce is really like for a single dad. Check out Magic Mike, I'm sorry, I mean Mortgage Mike on IG @mortgage_mike As always we're keeping it real and keeping the levity because this process is tough enough. But you are never alone. You got this and we got you. We MISSED you and love when you slide into our dms so reach out! @theandrearappaport @divorceattorneychicago


