Dear Jackass

Hello, Desperate!! If you are reading this, you've probably run out of options. Congratulations and Welcome to rock bottom!! Let me help you–because you clearly need it!!! jackassadvises@gmail.com Click on the About link below for the not-so-fine print/disclaimer.

recent posts

  • Podcast Episode: False Phallusies. Why do men feel it’s necessary to flaunt their phallus by mean

    Pip: Welcome to Dear Jackass — where the advice is unsolicited, the problems are deeply human, and today someone got a face full of evidence that modern dating is not going well.

    Mara: erica1837 is behind the advice desk this episode, and we have one letter that cuts right to it — unsolicited photos, the cowardice behind them, and what a person is actually supposed to do when that happens.

    Pip: Let's start with the phallus problem.

    False Phallusies

    Mara: The question on the table is a simple one with a complicated cultural answer — why do men send unsolicited photos, and what should a person actually do when it happens?

    Pip: The setup is almost too perfect: a compliment about a face leads immediately to an escalation, and the response in the column is direct — "I think the real reason men do this is because they are too cowardly to just say what they mean and get to the point. Do you want to get laid because I do."

    Mara: That's the real diagnosis here. It's not confidence — it's a workaround. The photo is a test balloon because asking directly feels too exposed, so instead the risk gets offloaded onto the recipient.

    Pip: And the recipient, for the record, did not ask to be a test site.

    Mara: The column offers several counter-moves. Ask him if he thinks it's handsome. Send back something equally unwarranted. Or — and this one is genuinely tactical — tell him it's cute, that you miss yours, and that you sometimes regret having it removed. The column's word for what follows is "crickets."

    Pip: That is a scorched-earth solution and I respect it completely.

    Mara: There's also a structural note worth taking seriously. The column points out the letter writer could have ended the text conversation at any point — it was in text. The exit was always available.

    Mara: The column closes with advice that is, on its surface, absurd and, on reflection, not wrong at all — get a dog, or find a woman who has one, probably drives a Subaru, and shares the pet with an ex.

    Pip: Honestly, as a lifestyle prescription, that holds up.

    Mara: The throughline is that the behavior isn't mysterious — it's just low-stakes gambling with someone else's comfort. The column names it plainly and the counter-strategies follow from that naming.

    Pip: Which raises the larger question of what we expect from people when the barrier to bad behavior is basically nothing.

    Mara: Dating, cowardice, and tactical exits — all in one letter.

    Pip: Same time next week, when the Jackass desk presumably has more mail, because it always does.

  • Hey, out of nowhere–on a scale of 1 to “backing your dad’s car into the steps and bending the door the opposite way” how’s your parking game holding up these days?

    Dear Backseat Driver:

    You have quite the memory. (Although I don’t know how anyone could forget about that.) That was twenty-five years ago!

    If you recall, that was not my fault. Aside from the fact I am a donkey and shouldn’t have been driving in the first place, I wasn’t the one who left the door open. The two in the back seat were fighting over who was sitting where and never shut the door all the way. I didn’t know, and when I backed up, it opened all the way and caught the stairs. All of this to pick up a pizza! Happy 20th Anniversary, Mom and Dad! (I should have seen this as a sign for those two. Who could have known they only had 5 years left?)

    Dad would have killed me if you all hadn’t been there. But it wouldn’t have happened if you all hadn’t been there, either. So this is one of those catch 22 situations. I will allow you to claim innocence on this one as you were just a passenger. But this is one of the only times you were innocent. How did my bed break again? Why did we have to sleep on the floor after that? You wild animal! Ha!

    I’m reminded of a time when the police showed up at my house–and we both thought they were coming for us about that car chase from the night before. Remember those five guys we were gonna fight at Taco Bell in Barberton and they took off–so we chased them in my Cadillac? Fun times!

    To answer your question: my parking game is beyond your scale! I haven’t torn off any doors or gotten into any accidents. And you’ll be happy to know I also got a new bed!

  • False Phallusies. Why do men feel it’s necessary to flaunt their phallus by means of pictures? Just recently encountered what I thought was a nice guy, exchanged numbers, and chatted a few times via text. He sent me a pic of his face, and I responded “very handsome.” He responded back with “If you think I’m handsome…” next thing I know–BAM!–hit in the face with a phallus. How is one to find a decent human this day and age? Best regards, Frustrated in phallus land.

    Dear Frustrated:

    Nice play with words here. Very clever. Are you a writer of sorts or just passing through? I have some questions and comments. Before I do, I must say…be glad you were only figuratively hit in the face with a phallus. I imagine it’s even more insulting literally.
    1. Your first problem is obvious. You were looking for a MAN. If you want a decent human–look for a woman!
    2. Have you seen his face in person or just in texts? How’d you get his number? If you’d already met in person, he only sent the face pic as a prelude to what was to come.
    3. You should have immediately asked him if he thought it was handsome. Then you should have started sending him other unwarranted dick pics–as I am sure you have some. (Do any women not?) Then you should have asked him if he thought those were handsome.

    This reminds me of a story about an old boss who was one of two owners of a company I used to work for. We were all at lunch one Friday, as always, and they were all drinking (I didn’t usually drink with them) and they were talking about something wildly inappropriate (and technically illegal) for a work setting (as always.) And this dumb, big-eared hillbilly was talking about his penis, and he said “He may not be big, but he’s cute.” I’m fairly certain only closeted gays think penises are cute. And I’m sure he’s secretly had more than any slutty women I know. That’s probably why his ears stick out so far. Guys grab onto them while he’s giving them BJs. He’s probably better than his wife at it. Back to your dilemma–

    I highly doubt this guy (or most guys) think it’s cute. They’re just hoping you do. You should have responded with something that would be completely disgusting or repulsive so his tiny friend would go back to his home where he belongs and he changed the subject. Then you could have removed yourself from the conversation. It was in text, though, so you could have at any time, anyway.

    I think the real reason men do this is because they are too cowardly to just say what they mean and get to the point. “Do you want to get laid because I do.” (When don’t they?) Instead, they play these stupid games because for the most part, they don’t easily meet some random nymphomaniac who’s as slutty as they want to be, so they have to test the waters. You don’t jump into a pool or lake if you can’t swim and hope you can touch the bottom.

    You should have told him it was cute and that you miss yours and that sometimes you regret having it removed. That would have stopped all communication. And if not–you have bigger problems and need other advice!!

    Or you should have said it was cute and sent him a pic of someone else’s dick and told him it turned you on. Crickets from there!!

    My advice: get a damn dog! Or—look for a woman who has one. She probably drives a Subaru, played college sports, and shares her pet with an ex.

  • Just curious, been reading your advice and you seem to be wise beyond your years for a little donkey. If you could be another animal, what would it be and why?

    Dear Curious George

    This is a question I am often asked, but here it goes. People often say they would want to be a bird so they could shit all over people they don’t like–or maybe even people they do. That’s so cliche and lacks imagination. They also clearly never thought that one through. I mean–who the hell wants to wake up so damn early every day, sing upon waking, and carry lice? Who wants to constantly build new homes only to find someone destroyed them? Who wants to fly south every winter? Sounds like a lot of exercise to me! Sure–the early bird gets the worm, but who the hell wants worms? I want pizza and cake. Nothing more. Nothing less. And maybe toss in a few veggies for good measure. And some whiskey just because. Why would anyone want to chew their children’s food up and spit it into their mouths? Really? Dirty little birds. No thanks!!

    It might be cool to be a Rooster. I don’t have to work for my food. I just stay home and eat whenever I like. And I wake everyone up when I get up. I have a nice yard and don’t have to deal with city people or noises. And when my owner says he has a giant cock, I can laugh because we all know he’s talking about me.

    I definitely wouldn’t want to be a donkey again. It’s overplayed since those damn Shrek movies. It got old real quick–like Home Alone. I mean, how many times can you forget your damn kid at home before a prison sentence happens? And how can those criminals be that stupid more than once? And don’t even get me started about The Fast and the Furious. What number are we up to now? 11? At their ages, who can believe they are either fast or furious at this point? They need to retire. As does this tangent.

    Maybe I’d like to be a lioness–the Queen of the jungle. She’s the most feared creature out there. She has the respect of everyone. She can eat anything she wants, doesn’t have to concern herself with her environment, and she stays warm in the winter. That sounds ideal!

    On second thought, I do think I would want to be a bird. Only I would want to be a free-roaming parakeet. I would fly around and tell everyone about themselves. And there would be no repercussions because I am a protected species. I would fly around and run my mouth–just like I do now–only in a much more fun and distinctive voice. I’d fly through the hood and tell those little hoodrats to pull their pants up, turn their shit music down, and stop smoking shitty weed. I would fly through the streets and stop at intersections and spew road rage because these assholes are either not using their turn signals or they’ve had them on for the last five miles. And don’t get me started on slow people in the fast lane. I’d fly into bars and instigate fights then fly away. I would fly to the schools in the suburbs and tell all of those little bastards they are not thugs, gangsters, or drug dealers. I would go to baseball games and taunt players. I would tell batters to swing at balls then tell them they’re going slow when running bases. I would go to ice cream stands and dive right at people so they’d get scared and drop their ice cream so I could have it. And I guess–if there’s time–I’d shit all over the people who deserve it. You know…help Karma along its way.

  • What do you wear to a CrossFit Competition when your wife is competing and has a bigger dick than you?

    Dear Body Builder:

    Are people still doing that? CrossFit is so 2017. I thought everyone left that for Planet Fitness sometime around the pandemic. Then they can work on their tan and bring all their friends for $20/month. And let’s not forget the free pizza. There are a few roads I can take you down to answer this. Why choose just one? Buckle up!

    First off–if your wife has a bigger dick than you, I gotta ask…is she trans?
    Secondly—doesn’t the spouse of every CrossFit bitch have a bigger dick? I’d bet so. CrossFit is like the Keto diet of diets. It’s a cheat. A quick fix. And beats the hell out of your body. And for what? To prove you can work out with a bunch of other douchebags in a smelly garage and roll around a giant tire and once a year go to some sort of bullshit CrossFit tournament where you compete against other garages? Get the fuck out of here, tiny dick! If you say burpees, I say, get me some beers. If you say box jumps, I say from one case of beer to the next.

    I once had a friend whose husband was a CrossFit instructor. And he competed in the douchebag Olympics. I’m not saying he has a tiny dick (don’t know or care) but I will say that vaginas are like tin roofs. If you don’t nail ’em enough, they end up at the neighbor’s. And that’s exactly what she did. Only he wasn’t her neighbor–if you get what I’m saying. Her husband has no idea. Good thing their kids look like him and not the “neighbor.”

    Did you know stress can take the sex drive out of men? Cause them problems with old one eye? Not having a penis myself (thank God), I had no idea. Women are wonderful that way. Men are always ready, and they are the ones who have trouble getting laid. I don’t know a single woman who couldn’t go out and get whatever STD she wanted any given night. Because there’s always a man somewhere. Back to CrossFit.

    That’s one hell of a spouse to attend and support the Douchebag Olympics! I would almost bet they are also a Brown’s fan. There’s no commitment like it! Hats off to anyone who would sit through that painful nonsense. It’d be like watching golf or NASCAR. It’s boring as hell until someone gets hit with a ball or gets too drunk and rolls their golfcart into a pond or gets a flat tire and crashes. It’s just not exciting. Until it is. But there’s no possible excitement at CrossFit. Someone splitting or shitting their pants during a dead lift or box jump might be hilarious–until you smell it. Add a bunch of people who smell like sweaty gym socks. I’m gagging at the thought.

    To answer your question: what do you wear–a dress and a picnic basket. And there better be a sandwich for her in there, you little bitch! And while you’re at it–make me one, too!


  • Why can’t people get fined for keeping holiday decorations up in their yard way past the holiday? Nobody wants to see the light up sleigh and reindeer amongst the tulips or Santa on your roof strapped to the chimney with the 4th of July fireworks in the sky.

    Dear Scrooge:

    What trailer park do you live in? They have yards? And a chimney?!? That’s fancy!

    I know these people you speak of. They go to Walmart in their finest pajamas and never clean the dog shit from their yard. They don’t mow the grass until they get a citation, and there are cigarette butts all over their driveway. They’re trashy but have that Christmas Spirit!

    You might be looking at this the wrong way. Maybe they didn’t leave them up way past the holiday but instead prepared early for the next. Christmas in July is only about two months away, you know. Or maybe…the neighbor gained so much weight that they are now too fat to climb their own ladder and have no way to remove Santa or bend over to pick up the sleigh and reindeer. Maybe they wanted to experience Christmas in a tropical place, but this is as good as it gets for them–because let’s be serious–even if they could afford to go on a vacation, the airport isn’t going to allow them to check their trash bags of clothes. Maybe they died in the house months ago, and instead of wishing for a fine, you should be calling the police to do a wellness check. You’ll know soon for sure when the weather really heats up.

    I could go on and on with the possibilities, but let’s be serious. There’s only one reason these decorations are still up: they are their finest possessions, and they are proud to give off Clark Griswold vibes all year long.

    Why don’t they get a fine, you ask? There are a few reasons. 1. Because we still have freedom in this country to be as trashy as we want. 2. Because even if it were illegal, the law has too much shit to do to worry about Santa’s reindeer getting a pickle tickle or enema from the tulips and other perennials. 3. Because you clearly don’t live in a place that has HOA fees. Perhaps you should look into that.

    If it bothers you that much, Grinch, find some neighborhood kids and pay them to steal their Christmas Spirit. Timmy needs new crutches, Scrooge.

  • My neighbors act like untreated grass is a cry for help. Meanwhile, their personalities need aerated. Where do we begin?

    Dear Peg Bundy:

    When did you move to Wisteria Lane? Didn’t you know this is one of those seven deadly sins. Thou shalt not let thy grass go untreated. You sinner!

    Where do we begin? Where DON”T we begin?!?

    I know these neighbors. The woman goes to church every Sunday while the man drinks beer and feeds his porn addiction. He makes a lot of money in some office because he kisses ass and not because he actually knows anything. She stays home and drives a minivan. They only have sex the one way, in the same place, twice a year, and they are both in denial that he prefers the company of men. She goes to Pilates and Yoga to pass the school days and secretly consumes 3 bottles of wine each day. They eat at home most of the time, and when they do go out, their asshole kids are unruly bastards, and they drink and ignore them for two hours.

    Since they are nosey, judgmental, and lead perfect lives, there are only two possible ways to deal with them: embarrassment or fear. Join the conversation. Help them out. I always say, if someone wants to talk then you should give them something to talk about. Go with a scenario that might be believable then run with it. Treat it like your last shot at an Academy Award and own it like you stole it. Then the last thing they will be worried about is the condition of your lawn.

    Here are some ideas.

    Tell the woman you can’t afford to treat your grass because your husband is still paying off the mob, and you are just glad they let him leave the family. Then ask them if they ever see a black Rolls Royce or Bentley drive by. Tell them if they do, they should go inside and stay there for 24 hours. They will pretend to feel bad for you but also scared for themselves. And they will stop talking to you altogether.

    Tell them you can’t afford to take care of the lawn because you paid your brother’s bond and are saving up for his prison sentence. They will either ask you why he went to jail in the first place and what he did that prison might be his future or they will just assume you are trash and leave you alone. They will feel bad for you but disgusted at the same time.

    Tell them you are having money troubles and ask if they could loan you some. They will scatter like hood rats in police lights because no one wants to lend anyone money anywhere.

    Tell them your first husband was abusive, and every time you didn’t keep up with the yard work, he would hit you. You finally couldn’t take it anymore and ran him over with the riding mower, and out of silent protest you refuse to do more than absolutely necessary. They won’t be able to decide if you are serious but will think you are nuts, either way.

    The next time they mention the lawn, ask them if they feel ok because they are seeing things. Convince them your lawn has been treated, and the weeds are a figment of their imagination. The lady will ask the other neighbors about the condition of your lawn but not before she pulls out another bottle of wine and considers whether she has a problem.

    Tell them you are getting some goats from a farm, and those goats told you they love to eat weeds. Convince them you are the goat whisperer. They will be pissed that you are getting goats but also afraid to say anything in front of you because you are clearly nuts.

    Whenever I am assessing a comedy crowd or my audience in public, I live by one rule: become someone you think they will find completely repulsive and let them think it’s you. Because let’s be serious…they will never think it’s them, anyway.

  • My 4-year old is still learning manners, but half the adults in public seem to have opted out entirely. Is there a remedial class for grown-ups?

    Dear, Mrs. Garrett

    I am guessing by your question, you are not or haven’t ever been a teacher. I am also guessing you didn’t ride the short bus or sit in classes with kids who did. There’s a short answer for this, but that wouldn’t be fun, would it? I shall take the long way–you know–like men do when they’re secretly lost and don’t want to tell you for fear you will make them ask someone for directions. The days before smart phones and google maps were wild. Even Mapquest was a bit primitive. Did you ever get directions that told you to drive to the edge of the Atlantic Ocean and swim 2,000 miles across? Fun times.

    Anyway, before I get to the point, I commend you on teaching your child some manners. For your sake, I hope this child is a girl. Because teaching little boys manners once they’ve realized they can pee anywhere they want is damn near impossible. Hats off to you, either way.

    This also reminds me of a time my mother and I were sitting in a hospital room with my grandmother who was just admitted with pneumonia. The nurse was asking grandmother if she had any pain anywhere. My mother pointed at me and chimed in, “yeah–a pain in my ass.” I acted appalled and offended and asked grandma, “Did you hear that, grandma? Didn’t you teach her any manners?” Grandma looked at me with complete demented seriousness and said “I couldn’t. I didn’t have time.” Mom and I burst into laughter, and the nurse got completely uncomfortable and said she needed to leave for a minute but would be back.

    I’m guessing you don’t have a stick up your ass like that nurse, but it is difficult. The problem you are having is you are asking the wrong question. There’s no point to teaching your child manners because they no longer exist. It’s like teaching her how to tie her shoes when they make plenty that have snaps, velcro, or slip on. Don’t let this kid become one of the short bus riders. Don’t let her get behind. Teach her important skills like the proper time and place to use profanity, martinis should be shaken and not stirred, and if 1 middle finger is good then 2 is better. Teach that kid gun safety, self-defense, and why it is important to have a good lawyer.

    To answer your question, no. There isn’t an adult remedial class for manners. And the reason for that is simple: these same people were already in all of the remedial classes, and they never showed up.

    If you teach this child to act wild and crazier than the crowd, everyone else will find manners out of fear. And that, my friend, is good enough.

  • Why would my ex-boyfriend’s girlfriend stalk my social media, stare me down, and shoulder check me in the hall 2 years after we broke up? How should I handle this?

    Dear, Rocky

    Are you even old enough to be on the internet? I remember when this was all farmland…you know…before Google. Well, you probably don’t know what I’m talking about. Google wasn’t always a thing. It’s been around since 1998 or something, but most of us weren’t wealthy enough to know about it for another decade. And by then there was internet porn and a million ways to steal music off the internet and turn it into ringtones for our cell phones. We didn’t care about Google because we were too busy naming our top 10 friends on Myspace, trying to navigate facebook–which was for college students only, and talk to all our friends on AIM. Does any of this make sense to you? It might be past your bedtime. Get a translation tomorrow. I wouldn’t want your parents to know you were up late reading complete nonsense. But since you managed to get online when you should really be sleeping, I will help you out.

    The reason you are being treated this way is simple: the girl secretly wants you. You know…like little boys would do in kindergarten. They were mean to the little girls they liked. Reciprocate the attention, love, and affection. I’m sure she will appreciate that. And might I ask–who’s bigger? Can you take her? Are you male or female? I’m guessing female–but this story would be even more interesting if you weren’t. It has some Shakespearean undertones…a sort of love triangle if you will. Ask one of your teachers who Shakespeare is and what these triangles were all about. It was the 1500’s. Everyone wore tights, acted like whiny little bitches, loved people who didn’t love them, and wanted to destroy anyone in their way. So basically–the same as they are now. (Why are men & boys wearing tights?) I guess we haven’t evolved much in the last 510 years–unless you’re talking about the furries. I digress.

    The real reason is simple: the girl is stupid. And like Gump’s momma said, “stupid is as stupid does.” Be flattered. If she’s formed this much of an opinion of you, it’s because you’re still talked about. And if you’re still talked about, it’s because your ex isn’t over you. He secretly wants you back. Or he’s convinced her that you broke his heart and it’s because you’re a shitty person instead of the truth: you’re just not into clingy crybabies–which she obviously is. And her last resort is violence (like any other barbarian) because she knows if she doesn’t try to take you out, there’s a chance you might want him back, and she can’t handle that. Suddenly–the participation trophy won’t suffice. Maybe get her one anyway–even if you don’t want him–just to prove a point.

    Now that I think about it, your ex might be a genius. He’s getting the attention he wants while trying to get two females to fight over him. That’s the high school equivalent of man-inches. Boys can say they’re still growing. But once you’re 25, and it’s still 3.5 inches, there are no more excuses. It is what it is, and you were better off to stay home that night. Don’t be stupid with her. Be flattered.

    If you must do something to stop this: I suggest a restraining order. If that’s too costly, switch teams. Flirt with her. Make them both think about you that way. Then take him back while she’s distracted. And as soon as he thinks there’s a chance, toss him to the curb, switch teams, and buy a Subaru. BECAUSE LESBIANS DON”T HAVE THESE PROBLEMS.

    And if all else fails, date one (or both) of their dads and become the wicked stepmother.

  • How do you handle a complete controlling lunatic who has no fucking clue what’s going on?

    Dear, Spider Web:

    That is quite a conundrum you’ve spun there. The answer is quite simple: you drink. A lot. And when you can no longer ignore him–because I am certain it’s a man–you leave. Because it’s not worth the jail time. But if you think is worth a little jail time, do it on a Wednesday. You’ll be out by Friday and can resume normal life. And by then, it’s the weekend. And who doesn’t love weekends? We all live for those, don’t we?

    All controlling lunatics have one thing in common: they have no control over anything in their miserable lives. So they try to control every little thing. They’re too stupid to realize that the only things they can control are their own actions…unless they have tourettes syndrome, schizophrenia, epilepsy, or extreme Autism. Or they are possessed by the devil. Then they’re fucked. We’re fucked. Everything’s fucked. I should hope this lunatic is more of the normal, narcissistic type of control freak. He probably has no friends, a tiny dick, and no girlfriend. (And I bet his hands are soft, too.) Just like the man who invented 40-hour work weeks. That guy’s gotta be dead by now. Just wait it out. I’m sure this guy will be, too. He probably has a little man complex and a huge ego. Wait it out. The Viagara will either give him a stroke or wear off, and everyone will know he has a little cocktail weiner like Justin Timberlake. Did you see that video clip of his concert? That harness revealed everything. It’s shit like that that makes it obvious God exists because there’s no way that gherkins got anyone pregnant without Divine Intervention. Back to tiny dick lunatic–

    What you gotta do is humor him. Tell him what he wants to hear, let him keep thinking he’s more than a fart in a hurricane, and do whatever the hell you want when you walk away. Because at the end of the day, your peace and self-preservation are worth far more than appeasing someone who’s never happy. It’s like trying to walk up the down escalator. It’s a waste of time. And when you’ve humored him as much as you can handle–walk away. Take your toys and your friends and go home. Leave him on the playground by himself. Then he will know how much control he truly has. He probably already knows, but he’s never going to admit it. Let the trash take itself out.