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

    • How do I talk my wife into a 2.5some with a midget?

      Dear Jolly Green Giant:

      I should assume by the question that you are, in fact, a person of normal size? In the legs, I mean. Not the third leg or Asian gerkins or whatever else you may have down there.

      Let’s get one thing clear: they’re called little people! Or at least that’s what the angry Chuckie Doll who lives in the building next door tells me. Also–don’t call them Chuckie dolls. Getting hit by a midget is like getting kicked by a toddler. I’d rather swing on a grown man. In prison. With nowhere to run and hide. Trust me on this.

      I have some questions. Is your wife of normal size as well? Do know any little people or are you just hoping to find one? If so–where does one look for them? I know three, and I didn’t go looking for them. Two I went to high school with, and this other one, well…she just appeared at my complex pool one summer day and thought she didn’t need to follow the rules. The deck said no diving, but she was diving into that bitch like she was practicing for the Midget Olympics, and she just won the gold! I was jealous. But that feeling soon drown when she told someone else at the pool she wasn’t going to the club that night because it’s loud, and all she smells is farts. Can you imagine? You are eye level to all the assholes!! And everyone farts because the music is loud and you can blame the smell on anyone. How disgusting!! I’d be finding a bf or gf that would let me ride them around town like a horse. No more assholes for me!!!

      Are you a man or a woman? Do you have a fetish, or is this a bucket list thing? Do you want the midget to be a man or woman? Are you wanting your wife to participate with said midget or just watch you? Does she drink? Do you? Will you need to? Will she?

      I guess you have to ask yourself this: what’s it worth to you? What are you willing to give your wife if she does this? Does she owe you any favors? You could always handle it The American Way: bribery or blackmail. You better hope she has none on you, though.

      Are you going through a midlife crisis? What are you wanting to get out of said 2.5some? Have you ever had a threesome? You might want to do that first because let me tell you…unless you and your wife are freaks, you can’t handle a midget!! The one I know is easier than velcro shoes and so kinky she would make Christian Gray blush. She’ll be jumping on you like she’s in the WWF and the fight is almost over!

      I’ll leave you with this: take your wife out for a nice dinner. Buy her flowers, a new car, a highland cow, whatever the fuck she wants. Then tell her this is your midlife crisis gift, and you prefer she be there. Then after she lets you come back to the bedroom from kicking you to the couch for two months, get that bullshit out of your head cause it’s never gonna happen!

      Look at it this way, Jolly Green: if she says no, then you don’t have to end a night by disappointing two women!

    • I’m premenopausal, and these hot flashes are killing me. One minute, I’m fine. The next, I want to rip off my clothes. I’m curious if I should get HRT or if there is a better solution. I’m concerned about the side effects.

      Dear Muumuu dresses:

      Why are you even asking me for advice? If you are old enough to have these issues, then you are also past the age of giving a rat’s ass what anyone anywhere thinks about any damn thing!!! Do whatever the fuck you want! Better yet–do something 10 times crazier, blame it on your age, and let everyone else think you are medicated and just missed a dose!

      I don’t know if you should get HRT, but I’m definitely on board with THC, ecstasy, and maybe banging your PCP–if he’s hot! Plan your midlife crisis. Go all out! Exhaust all possibilities before you get the granny dresses and compression socks because what immediately follows is a walker and a broken hip! Let’s not get old just yet! Your mind still seems to be intact.

      Life’s short, so there’s no point in being uncomfortable. If you are hot and need to rip those clothes off…there are only a few places I suggest you don’t do that. 1. The police station. Aside from the fact it is extremely dirty, they will arrest you. Try putting clothes on while also in handcuffs. 2. While driving. If you get pulled over…see 1 above. 3. Riding any public transportation. It’s hard telling what disease you’ll contract there. 4. While baking, cooking bacon, or shaving your legs. I know lefty and righty have already headed south for the second half–and you don’t want nipple issues on top of these flashes. You think you’re burning up now!!

      I would say, let nature take its course. If muumuus are cool, get ’em. See if they have some without sleeves. If not, invent them! Give up clothes. Go to naked campgrounds, beaches, and yoga. But beware–you’ll see more weiners than the Ball Park Distribution Center. And who really wants to see that?!? Unless you’re already a lesbian. If not, then welcome to your new midlife crisis!

      The solution: don’t trust the government, big pharma, or any doctor. Don’t add to or take away from anything–unless it’s your clothes. This time of life gives you a chance to be naked–because before you know it–you’ll be cold all the damn time and wearing sweaters in the heat of summer.

    • How do you deal with in-laws that try to control your life?

      Dear Mrs. Yoder:

      First of all–why did you get married to begin with? How long have you been married? Do your in-laws just try to control you, or do they control your spouse as well?

      I am almost certain I know the answers. I am guessing you are a female, straight, and your in-laws already control your husband. How old are you? I’m guessing young. If I were to guess the situation…it would be like this…

      You are newly married because you wouldn’t be questioning the control if you weren’t. They would either already be controlling you, or you would be ready to check out.

      And the reason they are trying to control you is because they control him. It’s a weird Oedipus Complex–but instead of the son wanting to marry mommy, mommy has some sickness of wanting to marry her son. That’s why she won’t get him off the tit. Is she also religious? I would guess so. She probably thinks she’s protecting her son by being contentious about everything where you’re concerned. And his parents think he’s too damn stupid to run his own life–which he is–but they are just as fucking stupid if not moreso since they’re older. And he just won’t unlatch. It’s better that he stretch out her tits than yours, anyway. I digress.

      The problem is, they think you are the devil for trying to get him to think on his own, and they probably use religion as a weapon to brainwash him and convince him you’re the problem when in reality he probably has a porn addiction and would rather hump the blankets than his wife. Sounds like he’s either into mommy or other men. Is he Amish? If so, his name is probably Oedipus Yoder–in which case, you need to climb the fucking fence and come back among the land of zippers and dolls with faces. And if he has a sister, she better run because she’s probably next.

      My advice, Mrs. Miller, is simple: Get a divorce and run as fast as you can. Because unless you wanna share mommy’s tits, you’ll never have his attention.

      Climb the fence. Find a boyfriend. Buy some pants with zippers. Sign him up for every dating site that exists. Do you have pictures of him at his most vulnerable? Use those for the profiles. Carry a permanent marker with you. Write his contact info everywhere you can. And sign him up for porn addiction meetings, sex toy shop giveaways, and applications for every gay bar in town. Because if we were being honest, he’s afraid of women and prefers men, anyway.

    • Why does my boss always answer a question with another question?! Like why make it more complicated than it needs to be?!

      Dear Confused in the Corporate World:

      Let me start my answer with questions. Is this boss a man? I would bet my (jack)ass on it!

      What types of questions are you asking him? Are you asking him in person or virtually?
      If you are asking for a raise, and he responds with a question–he doesn’t think you deserve one. And even if he thinks you do, he’s worried that will take away from the bottom line and his raise. So that’s a polite “no.”
      If you are asking follow-up questions from a meeting–he wasn’t listening, either! He was probably drinking wine from his coffee cup and even blowing on it to look legit. And He was probably wearing nothing below his shirt and tie but some tidy whiteys with skid marks. And maybe some flip flops. Because he has to take the dog out on his leash because a tree fell in the back yard and he’s been too lazy and cheap to get the fence fixed.
      If you are asking for time off–he’s thinking of who he can pass your work to if he approves it because he’s certainly not going to do it! He has to walk the dog, you know!
      If you are asking him about promotions or positions or anything involving staffing–he doesn’t really care as long as it doesn’t result in him doing more work. And actually, if he thinks he can do less…there goes the hamster wheel.

      This situation you speak of reminds me of undergrad. I had this evening class, Grammatical Structures. The professor was a lovely man. He was short and small in stature. He wore a hat that looked like something a train conductor would wear. So, I called him the conductor. A few of my friends were in that class, but otherwise it was a snooze. The textbook was called Doing Grammar. My best friend, Jim and I would always say “do grammar before grammar do you” among other obnoxious things to entertain ourselves. (I wrote my first movie during that class. I was so productive. And bored.) Anyway, this class was a split 400/500 level class. Half the students were in grad school. They were all teachers in their mid to late 50’s. They all worked in the same district and knew each other. It was like a tiny cult. And they did the same irritating bullshit. Every time the professor would say something, one of those assholes would raise their hand then ask him the very thing he just said. Like–weren’t you old fucks listening? Turn up your hearing aids, dickheads! I called them the postmortems. I thought no one besides my friends knew of my nickname for them–only to come to class one day, and none of them were there. The professor came to the back where Jim and I sat and asked me where the postmortems were. I laughed nervously, wondering if he knew he was the conductor.

      Back to your dilemma, Confused. The real reason your boss answers questions with more questions is simple. He does this for a few reasons. He wants to confirm he understood you because he wasn’t listening. He wants you to figure it out yourself. And most importantly, he really doesn’t know the answers.!!

      The solution to your problem is simple: do whatever the fuck you want and tell him later. It’s better to ask for forgiveness than permission. And if he continues to respond with questions, ask him some extremely personal and uncomfortable questions just to make him squirm a little. Or…respond by asking more questions. Play his game. All day. Because even a salaried employee is paid by the hour.

    • How and when do you just give up?

      Dear Quitter:

      I have questions. And always answers. It depends, my friend. What are we giving up?

      If it’s meth–right after that last tooth falls out. You don’t want your dental bill to be more expensive because they have to remove any first. Get ready for new pearly whites! And don’t forget a gold one!

      If it’s underwear–never. Because skid marks. Plus you’ll really learn how farting releases particles. It’ll be shit glitter in your pants. And who wants ball chafing? Or kitty rash?

      It it’s other people’s opinions–yesterday! Because who gives a fuck what anyone else thinks?!? Most people aren’t even smart enough to ride the short bus.

      If it’s sleep–that depends. I know I turn into the hulk if provoked. And then an MMA fighter. Followed by a whiny toddler. Let me sleep!!

      If it’s drugs or alcohol–why?? Who doesn’t want to be numb? Too bad smoking weed makes people dumber. Many of them were already licking the windows on the short bus. Now they’re licking the seats. Naked. Because they misplaced their pants.

      If it’s bad habits–define bad. It’s all in how you look at things. Optimism turns bad into good.

      If it’s a relationship–Tina Turner said it best. “What’s love got to do with it?”

      If it’s work and your boss–see the answer for other people’s opinions! YESTERDAY!! Because why care and work hard for some ungrateful shitbag who drinks all night, sleeps all day, and chases girls who are young enough to be his daughter–only to go home and jerk off alone, anyway?? The true mind fuck is this: the ungrateful millionaires we work for are taking way more from us than people fucking the system. You don’t have to work for the man if you become him.
      How to go about this: buy your boss a condolences card and tell him you’re sorry for the loss of one of the best employees he’s ever had. Then buy a sheet cake for your coworkers, congratulating yourself for moving on. But before you do all of that–make sure you’ve made the most of your situation and gotten anything and everything you can. Use up all your vacation. Or…you could do the unthinkable: call ICE and have him deported. If that doesn’t work, call a local prison and tell them you think he escaped. Whatever you do, make the exit unforgettable!!

      Most importantly–if it’s this page: Never!!! Because the nonsense will get better and better. And eventually, it’ll be like shit glitter. Everywhere!!

    • 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!