Jacob Behrendt
Pretty huge Dilemma Podcast
Join Jacob every Thursday as he dives into random thoughts and questions that pop into his head - some big, some small, but all with a pretty huge dilemma attached. It's authentic and unpolished, just him working through ideas, figuring things out, and getting better with each episode. No audience, no pressure, just an honest exploration of dilemmas, one thought at a time.
Author
Jacob Behrendt
Category
Podcast website
Latest episode
Jul 11, 2026
Where to listen?
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Episodes
My House Got Volunteered | Pretty Huge Dilemma #48 11.07.2026 34:40
Someone tried to volunteer my house for a holiday party and I quickly thwarted that idea. Also some thoughts on why fireworks keeping you up at night might actually be an insurance issue, the Toy Story characters who aged well and the ones who didn't, and a case for comedian encores that would revolutionize the event. Like, Subscribe, and Comment to support the show!
Fireworks Are Overhyped & Pushing Pills in History | Pretty Huge Dilemma #47 04.07.2026 30:52
Officially decided fireworks are not worth watching anymore and the dogs are the only ones who had it right. Also what year could he go back to and actually be a useful doctor? Turns out not many, and the answer is mostly just prescribing pain pills and hoping for the best. Plus a witch debate that nobody asked for but got resolved anyway. Like, Subscribe, and Comment to support the show!
Bad Driver Stickers & Too Friendly Service | Pretty Huge Dilemma #46 27.06.2026 38:45
People should be given bad driver stickers instead of tickets occasionally. Also, a food order that came with too many questions and an employee not knowing what is on the menu. Lastly, why do trash cans need to be cleaned? Sounds like a waste of water and soap to me. Like, Subscribe, and Comment to support the show!
Not a Facts Based Show | Pretty Huge Dilemma #45 22.06.2026 34:25
The podcast got some NASTY comments that need to be addressed. Evidently people thought this podcast was going to be 100% right about everything all the time. After dealing with this dilemma, Jacob brings up a home feature everyone should install. Lastly, do you think some of the state boundaries should move? Might be time to change some things up. Like, Subscribe, and Comment to support the show!
Netflix Debut & Backyard Clean-up Gone Wrong | Pretty Huge Dilemma #44 13.06.2026 35:40
It has been decided bless you is a pointless social norm and is done saying it. Also attended a Netflix taping and can't wait to see if I make on the big screen. And a backyard situation that may have caused some minor household tension. Like, Subscribe, and Comment to support the show!
Pickup Basketball Return and AI Taking Over | Pretty Huge Dilemma #43 06.06.2026 33:02
This week covers AI tools are running the podcast behind the scenes, surviving a pickup game with zero points and multiple airballs, and a partial break down of the Enhanced Games. Like, Subscribe, and Comment to support the show!
Fireworks Mishap & Major vs Minor League Sports | Pretty Huge Dilemma #42 30.05.2026 39:12
A conversation about summer sports somehow turns into fireworks stories, minor league baseball debates, and realizing some childhood decisions probably should not have worked out as well as they did. Some ideas sounded smarter at the time. Like, Subscribe, and Comment to support the show!
The Gym Class Decathlon | Pretty Huge Dilemma #41 23.05.2026 28:56
A normal conversation somehow turned into breaking down gym class athletics like it was professional sports analysis. From dodgeball strategy and Wiffle ball physics to the realization that gym class may have had the most complete athletes of all time, a few topics probably got analyzed way more seriously than they should have. Like, Subscribe, and Comment to support the show!
Motivational Hater & Fixing Festivals | Pretty Huge Dilemma #40 16.05.2026 27:19
What started as a pretty normal conversation slowly turned into debating things that probably didn’t need this much thought put into them. Somewhere along the way we got into raw fish at elevation, music festival survival tactics, and why MLB position players throw like somebody’s dad during batting practice. Like, Subscribe, and Comment to support the show!
The Denver Vacation Spiral | Pretty Huge Dilemma #39 09.05.2026 37:08
Thought a quick Denver trip would be simple until every part of traveling started becoming its own dilemma. From rental car problems and tipping confusion to Casa Bonita and the realization that vacations somehow create more work when you get back home. A few things went smoother than expected… a few definitely didn’t. Like, Subscribe, and Comment to support the show!
Watching Contractors & Unique Cooking Habit | Pretty Huge Dilemma #38 02.05.2026 31:09
Trying to figure out what you’re supposed to do when a contractor is working in your house and why it somehow feels awkward every time. Trying to watch them without obviously watching them. Also, I get into shipping delays that still don’t make sense, phone storage struggles, and a kitchen hack you have to try! Like, Subscribe, and Comment to support the podcast.
Casino Trip, Negotiating Prices, & Cemetery Taxes | Pretty Huge Dilemma #37 25.04.2026 27:14
Trying to handle contractor quotes without folding right away and why that’s harder than it should be. Also little trip to concert at the casino caused me to lose money way faster than expected and working to justify what I ate to push down my emotions. Make sure to Like, Subscribe, and Comment to support the podcast. #comedypodcast #casinotips
Expired Friendships & Space Toilets | Pretty Huge Dilemma #36 18.04.2026 36:10
Even in full home contractor mode, the dilemmas don’t stop. Talking through random homeowner realizations, social media annoyances, space travel thoughts, and a clip I can't stop laughing at. Just another episode of figuring things out in real time. Make sure to Like, Subscribe, and Comment to support the podcast.
Debunking Migraines & Space Travel Problems | Pretty Huge Dilemma #35 11.04.2026 27:47
This episode continues the trend of questioning random observations and fixing everyday frustrations. We get into controversial health opinions, question whether migraines are misunderstood and explore why astronauts might be built different. We also dive into why pharmacies should be run more like Chick-fil-A drive-thrus. Like, subscribe, and comment to support the podcast.
MLB Preview & Stand-Up Fear | Pretty Huge Dilemma #34 04.04.2026 36:28
This episode covers everything from making MLB predictions for fun to the very real anxiety of possibly signing up for Kill Tony. We also get into Iowa’s unexpected run, questionable wrestling traditions, and what it actually means to call podcasting a hobby versus a career. Nothing should be be taken too seriously. Like, subscribe, and comment to support the podcast.
March Sports Calendar is Broken & How to Fix It | Pretty Huge Dilemma #33 28.03.2026 34:57
March is absolutely broken. Too many college postseason games stacked at the same time… there’s physically no way to watch it all. Meanwhile, my food review series has quietly turned into me eating candy every week. Not ideal. So now we’re solving two dilemmas: fixing the March sports calendar so humans can actually enjoy it and figuring out how I got here nutritionally. Like, Subscribe, and Comme...
Midwest Travels: Weird Food & Small-Town Life | Pretty Huge Dilemma #32 21.03.2026 34:26
Join me on a chaotic trip through Iowa, from bizarre Midwest salads to mystery shrimp in a landlocked state. Served with a side of “Iowa look-alike” observations and gardening intimidation tactics. Insights you won't get anywhere else! Like, Subscribe, and Comment to support the podcast!
Childhood Friends to Podcast Arguments | Pretty Huge Dilemma #31 14.03.2026 48:43
A childhood friend joins the podcast and we go through how we got to this point. Couple rough moments we barely made it through. Along the way we debate whether a California roll is a complete waste of money, and somehow end up discussing the genius behind the ranch milkshake. Like, subscribe, and comment to support the podcast.
Godfather Planning & Critiquing Hibachi | Pretty Huge Dilemma #30 07.03.2026 37:38
After a long day of yard work and pickleball, I still found the energy to tackle some very important dilemmas and deliver truly one-of-a-kind insights. Is showing strategic interest now just to secure a future Godfather title the right move? And could the entire delivery system of hibachi be… improved? Like, subscribe, and drop a comment to support the podcast.
Medieval Times & Modern Pettiness | Pretty Huge Dilemma #29 28.02.2026 42:12
This episode starts at Medieval Times, where grown adults fully commit to cheering for knights like it’s the championship game. Then we get into the only acceptable way to get even with a car repair shop: aggressively taking the free waiting-room snacks. And finally, the moral dilemma of wanting to support local farms but not wanting to pay free-range prices if it only saves a couple bucks. Petty?...
Gas Laws, Dad Powers, & Wrestling Loyalty | Pretty Huge Dilemma #28 21.02.2026 42:13
We’re diving into everything AND the kitchen sink this week! Why my desk clutter expands to fill any room but everything has a placeMy theory on which weight class makes the best head coaches. A business plan to make cooking dinner easier. Help us grow the podcast! Like, subscribe, and comment your thoughts
Rainforest Cafe Air Quality Plan | Pretty Huge Dilemma #27 14.02.2026 40:08
This episode is full of small dilemmas and big overreactions. Hard to decide whether it’s better to buy one air purifier or enough plants to turn my house into a Rainforest Cafe. Waking up not being and one of your body parts not working properly is a terrifying way to start your day. Make sure to Like, Subscribe, and Comment to support the podcast!
Girl Scout Cookie Rankings | Pretty Huge Dilemma #26 07.02.2026 45:41
In part two, we create definitive rankings of all the girl scout cookies we could get our hands on. This might be the most serious and intense discussion we have ever had. Do you agree with the rankings? Like, Subscribe, and Comment to support the podcast!
Anti-AI Stance and Waste Buying Flowers | Pretty Huge Dilemma #25 06.02.2026 28:02
Ashley is BACK! This time with more dilemmas that need solving. First, we break down why she doesn’t like using AI and why it makes her uncomfortable. Then I shock her by knowing her favorite flower. Then lost those point by immediately revealing how much they cost and why I refuse to buy them. Like, Subscribe, and Comment to help grow the podcast!
Past My Skiing Prime & Being Class Distraction | Pretty Huge Dilemma #25 31.01.2026 43:14
This episode is full of honest confessions and questionable moments. We talk about being past the age for risky activities, an embarrassing first date, and an action in class that brought every to a halt. Make sure to Like, Subscribe, and Comment!
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