Is it okay to fail?
Hell yes. It’s necessary.

why does it bother me that my boyfriend is bisexual even though I spent a decent part of college hooking up with other girls at parties
Because there’s a double standard with regard to male bisexuality in our culture, and you’ve unthinkingly made it a part of your value system.

“Hooking up” sounds too juvenile and “sexual relations” too Bill Clinton-y. How should I talk about sex with my therapist?
Don’t modify your language to suit your therapist. Say whatever the fuck you want. Whatever gets it out of your mouth is best.

Found $100 on the ground, not attached to a wallet so I can’t really return it. I feel guilty spending someone else’s money, but just keeping it doesn’t mitigate their loss. Where would you donate it, charity makes everyone’s world better right? Sidenote: Should I have just walked past it? Kind of feel weird that I even picked it up.
If you want to donate it, give the hundred to Planned Parenthood. It’s okay to keep it, though. You haven’t done anything wrong.

Are there any sports where women could hold their own if we had integrated men’s/women’s teams?
Baseball, soccer, tennis, and golf leap to mind, but what the fuck do I know?

Have you seen the series Transparent? Should I start watching?
Yes. It’s amazing. The performances are so damn good. The Pfeffermans are a brilliantly written family of spoiled rotten narcissists, each of whom you’ll either love or love to hate. Give it three episodes and you’ll be hooked.

Would you bother taking an ex to court for money they owed you? Or just write it off as an expensive bullet you thankfully dodged?
If the amount belongs in small claims court, I’d let it go.

How did you find drug connects in your new town?
I’ve deliberately chosen not to find drug connects in my new town, but if you’re asking for yourself, the answer is to hang out with people who do drugs.

Do you listen to vinyl?
I have a small but respectable collection.

Where’s the line between empathy and enmeshment?
Empathy and enmeshment aren’t really on a spectrum, but what I think you’re really asking is, “at what point does my concern for others become an unhealthy level of over-concern.” The answer to that question is the point at which you start allowing your personal boundaries to break down or be violated.

Should I become a psychiatrist or should I become a lawyer? Help, I can’t decide.
Split the difference and become a forensic psychologist.

I have never been in love. I like who I am when I’m with him. But I’ve got this knot in my chest, sometimes I want to cry. Everything about this terrifies me. I’m not ready to share myself.
Yeah. Cupid doesn’t give a fuck whether you’re ready to share yourself. Welcome to being in love.

How do I start to recover from what seems to be PTSD from a rape? It’s been six months and I’m starting to feel it.
I highly recommend EMDR therapy for PTSD. That shit really works.

I’m 24. Just found out he’s 37. First date this week. Is that too old?
Some people will think so, but then again, who gives a fuck what some people think? What do you think? Besides, it’s just a first date. Go. See what it’s like. Maybe you’ll appreciate dating a little older, maybe not, but you won’t know until you try.

We recently shifted to a long distance relationship. Is it unreasonable for me to expect more effort in mental or emotional needs because the physical aren’t being met?
It’s not unreasonable, but that doesn’t mean it’s possible. You’re gonna have to ask your partner for what you want. Be specific.

What makes a spark between two people?
Chemistry.

Do you think Republicans are bad people?
Some of them. Mostly, they’re just people with bad ideas.

How can you call yourself a feminist and then sincerely endorse Clinton? Do you hate women, or are you just rich?
Yikes. This level of black and white thinking is kind of a red flag. Is everything okay with you?

How/why did you pick your handle “Dear Coquette”?
I didn’t really pick it. It picked me when I started writing professionally. Coquette is a double entendre and sly nod to my former and less appropriate handle from the early days of Tumblr. If you’re new and don’t know what I’m talking about, stick around for a while. You’ll figure it out.

I’m embarrassed by how much I’ve revealed to you over the years.
Since I can’t reach through my computer and slap you upside the head, please slap yourself upside the head on my behalf. (Do it out of love, though, because you’re being ridiculous.)

are politics + economics just our egos fighting each other over who is right?
Nope. Politics and economics are just our species fighting over who gets the limited resources.

I have an opportunity to work in New York doing what I love. I currently live and work in Miami, where I’ve spent all my 25 years. I’ve been pushing to leave, but now when I have the chance, I’m terrified. I feel like I’m at a standstill.
Go. Just do it. You’re ready. It’s the perfect time, and being terrified is half the fun.

You answered a question I wrote a while back about cocktails, and while I still love them, my drink of choice is now Scotch. Should I be concerned that my tastes are so easily influenced?
Is your drink of choice now Scotch because I led you to the simple discovery that whiskey is fucking delicious, or did you stop drinking cocktails because I said that nine times out of ten they’re too sweet for my taste? If it’s the former, you’re fine. If it’s the latter, you should be concerned about how easily you’re influenced.

“I need to be loved to feel worthwhile.” This is the answer that came up when I asked myself in half sleep why I would feel depressed if I saw no friends this week-end, because I don’t have real friends in this town I have lived in for more than three years. Is this fucked up?
It’s not fucked up if you can shorten your phrase to simply, “I need to be loved.” We all need to be loved, but feeling worthwhile can’t ever depend on someone else’s love or approval. That’s super unhealthy. It’s the primary ingredient in every enmeshed and codependent relationship.

I wish I could have told you everything, so you could have warned me.
It wouldn’t have mattered. The person you were then wouldn’t have recognized the warning. Some shit you just gotta learn the hard way.

My mom found my copy of The God Delusion. She cried.
Good.

This is kinda random and really nitpicky, but why do some of your @ replies on Twitter begin with a period before the user’s Twitter handle? It’s just something that I’ve noticed over the years.
That’s a thing people do if they want an @ reply to show up on their main feed like a regular tweet. It’s the equivalent of inviting everyone in the room to listen in on your conversation.

You’re definitely looking for deep connection. Is it because you moved to a new place? When I moved across the country I was super desperate for connection.
The exact opposite, actually. I moved to a new place because I was looking for a deep connection.

I keep getting this fleeting empty feeling inside my chest. I’m not even sure if it’s emptiness or dread. It feels like when a coke comedown hits although I haven’t done hard drugs in years. It lasts a few seconds each time and it’s happening more frequently. What is going on with me?
That’s what’s known as a limited symptom panic attack, but since technically you’re describing mild chest pain with increasing frequency, I’m supposed to tell you to go see your doctor. If you do, make the trip worthwhile and ask for some Xanax.

Sex is disappointing. I am still attracted to him. What now?
The term “disappointing” is vague, but it implies room for improvement and a willingness on your part to give out gold stars. If you’re into him and you’ve got the patience, then you know what they say. Practice makes perfect.

Can someone have a legitimate relationship with a person whose identity they fetishize? (Legitimate in this circumstance is defined as loving, long term, and egalitarian.)
Sure. I know plenty of Jewish guys in loving, long-term, and egalitarian relationships with Asian girls.

Why does him not wanting to fuck me anymore hurt even though I’m in love with someone else?
Because even when it’s appropriate, rejection is still rejection.

He’s an arrogant, asshole, condescending lawyer, but I’m so into him. Why am I so into him?
Because you haven’t learned your lesson. (Yet.)

Are all talented artists insecure, hypocritical, high-maintenance and generally toxic? Or is it just that I’ve been exposed to an unfortunate select few who were actually human garbage?
I mean, not all of them are, but yeah, you’ve stumbled into reliable territory with your characterization.

Supreme Court nominees aside, don’t you think Cruz would be marginally better in terms of how other countries view America?
Set the balance of the Supreme Court aside because you’re concerned how other countries might view America? Are you fucking kidding me? That’s like setting aside the cure for cancer because you’re concerned what other people might think if your hair falls out.

It doesn’t bother you that Megan Kelly is racist?
Dude, she’s a Fox News anchor. I don’t wanna date the woman. The fantasy was a hot older lesbian hate fuck. The fact that she’s racist kinda makes it hotter.

Why do people care so much about your age?
People want to know my age so they can triangulate my wisdom.

I miss your long-format personal writing. Please tell me something good.
Okay.

Are feelings rational?
Feelings are emotions that have come into awareness. It’s not that feelings are irrational. It’s just that rationality doesn’t apply to feelings. Rationality applies to thoughts. The way you think about your feelings and any subsequent behavior can be rational or irrational, but that speaks to the thoughts and behaviors, not the feelings themselves.

Love will never be possible for me because no one will ever live up to my standards. I want someone who’s smarter and more confident than me. Someone to make me a better person. Mostly I want a man and not a boy. So how do I go about solving this problem?
There is only one problem here to solve. You want someone to make you a better person. Fuck that. It’s poison. You will never be happy as long as you expect someone other than yourself to make you a better person. You can have all the rest of it, but you have to take responsibility for your own self-improvement.

My boyfriend of five years just told me he would buy me razor blades if I would kill myself with them. I feel low.
Yeah, you are a victim of emotional abuse. That’s real shit, and it has the same cycle with the same long-term damage as physical abuse. Five years is enough, wouldn’t you say? I know it’s scary, but I think you might find that you’ll feel surprisingly less low if he was out of your life.*

*I got your second letter. You don’t need a breakup. You need immediate domestic violence intervention. Your situation is very serious. Please send me your email and let me know what city you live in, and I will try and help point you to some local resources. 

We’ve been together three years. Aren’t the trust issues supposed to go away after a while?
Time isn’t what cures trust issues. Integrity is, but all the integrity in the world can’t get through without open, honest communication. That’s why it’s taking so long.

Why am I always suspicious of men who express an attraction to my looks? What am I afraid of?
It’s not that you’re afraid. It’s that on some fundamental level, you don’t believe them, and so that automatically makes you suspicious.

Hypothetically, let’s say I get permission from his wife to fuck him. Isn’t it still unethical because I’m responsible for taking away time from his home and kids?
Nah, if they’re in an open relationship and you get his wife’s permission, it’s no more unethical than if he took that same amount of time to go play a round of golf. Parents are entitled to personal recreation, and I’m sure he knows better than to be off fucking you instead of showing up to a parent/teacher conference.

On Friday we informally (on snapchat) joked (but not really) about not seeing anyone else but each other. On Saturday I had amazing (unplanned) sex with someone else…
If you’re writing me, you must be feeling guilty. That’s a good thing, because it means you have a conscience, and you also like this guy. If you want to be exclusive with him, make it a real conversation, and stick to your word.

What do people like you who happily go around saying ‘fuck the police’ think would really happen in a world without police?
There are many versions of a world without police. Some are a feudalistic horror show, and some are a utopian ideal. We haven’t reached a point in our sociological evolution where police aren’t necessary, but we have reached a point where it’s okay to acknowledge that they are, at best, a necessary evil. If you’d like to know more about what I mean when I say fuck the police, feel free to read, “On fucking the police.”

Do you think you’re in your last lifetime? I’m betting you’re an old soul and have learned a lot of past life lessons. Hence why you’ve become an “Accidental Guru.” Maybe you are more of a real one.
There is only one life.

Was Amber Rose’s tweet about Kanye liking assplay homophobic and super awful? I feel like its small change compared to his whorephobia and misogyny but I’m afraid I’m biased.
Weigh in please.
It’s a fine line, but these days I think it’s a stretch to call that tweet homophobic. Her reply was definitely an attempt at emasculation, but I interpreted it as an assertion of sexual dominance, not an accusation of homosexuality. After all, the hashtag was #FingersInTheBootyAssBitch, not #FingersInTheBootyAssFaggot. Admittedly, the type of toxic masculinity that is emasculated by sexual dominance is the same type of toxic masculinity that equates assplay with homosexuality, which is why I say it’s a fine line. Still, that’s not on Amber Rose.

I’m happy again and I’m really afraid something is going to happen.
You may be in a happy place, but you’re not nearly as happy as you could be, because you haven’t gotten rid of your underlying anxiety. All you’ve done is shifted it into the future. Well, guess what? Something is going to happen. Eventually, life will come along and kick your ass. The trick is to let that be okay. An even better trick is to also let it be okay whenever it happens. I don’t mean roll over and take it. I just mean accept the inevitability of it. I know it’s easier said than done, but that kind of acceptance is the antidote to anxiety.

What’s the cutoff date for being with someone you’re not in love with? Where’s the line?
You gotta draw your own lines, but being in love isn’t a binary state. It’s fluid and messy and emulsified with all kinds of other emotions. If you’re in a relationship where too many of your physical, mental, and emotional needs aren’t being met, ask yourself, is it possible that they ever could be? If so, would it be worth the effort? They are tough questions, but if you can answer them honestly, then the day you’re absolutely sure that your answer is a firm no, you’ve found your cutoff date.

I’m at a university that has a much larger male population. I have my pick of guys, he has virtually no chance with anyone else. How do we deal with this power imbalance?
In a healthy relationship, that wouldn’t create a power imbalance. It only creates a power imbalance if one of you uses it as emotional leverage, and that would be a pretty strong indicator of something unhealthy. You asked this question because it’s obviously come up, but I don’t know whether he’s wielding it as a source of insecurity or you’re wielding it as an excuse to take him for granted. Either way, you two better button that shit up, or it’s gonna be the thing that ends the relationship.

Wait, so what is the difference between overfunctioning and underfunctioning relationships?
No, I wasn’t clear on that. An overfunctioning/underfunctioning relationship is a type of relationship in which one partner overfunctions and the other partner underfunctions. Think of it as being lopsided, but also reciprocal. One partner usually gets blamed for being dysfunctional, but it’s really both of them together who cause the dynamic.

I got pulled over for speeding and the cop let me off with a with a warning but gave me a ticket for not having a seatbelt on. I took the seatbelt off after I got pulled over. I should be happy that I got off on the speeding, but why does the seatbelt ticket bother me so much?
Think of it this way, if you hadn’t taken off your seatbelt, the cop would have written you up for speeding. You were gonna get a ticket no matter what. It’s not that he let you off with a warning so much as he wrote you up for the violation with the least likelihood of him having to show up for traffic court. (If you have the time, contest the violation. Fuck the police.)

I’m aware that I’m being manipulated but in the face of sad puppy eyes and other various circumstances I seem to let it happen. How do I build up my sad puppy defenses? This same person manipulates everyone else I know and it’s infuriating. No one seems to be immune.
This is one of those times when it’s smart to use your temper. (Don’t lose your temper. Just use it.) Train yourself to get a little angry when you’re being manipulated. That’s the best defense against sad puppy eyes. (You’ll get a bratty reaction, but if the manipulation no longer works, it will quickly stop.)

At what point do complementary personalities in a relationship become incompatible personalities?
When the things you have in common form dysfunctional patterns of behavior.

How do I stop craving Chinese food?
I find the quickest way is to eat some Chinese food.

My pride says no and my curiosity says yes. What do you say?
Let your conscience be the tie-breaker. (I am not your fucking conscience.)

If you’re all about killing your ego, why do you refer to yourself as a guru?
Because my ego isn’t dead, and it has a very dry sense of humor.

When you talk about love, I feel like it’ll never be possible for me. What’s wrong with me?
Nothing is wrong with you, but you should ask yourself one question: Why do you feel like love will never be possible? When you can clearly answer why, write it down. Pin it up on the wall and stare at it. That answer is not you. That answer is your enemy. That answer and all of its triggers and sources are everything you should rail against and reject. Now pull that answer down off your wall and light it on fire. Fuck that shit.

I have daddy issues. He has mommy issues. How do we capitalize on this kinky shit without forging a disturbing codependency?
Your use of “kinky” implies that the daddy/mommy thing is playing out in your sex lives. If that’s all it is, you two are fine. (Well suited for one another, actually.) If it’s more than just kink, and your respective parental issues are about enmeshment, then codependency might become a problem. Just watch out for unhealthy patterns of behavior that you recognize from your respective families, and if you catch yourselves becoming your parents, maybe jump into a little couples counseling before things get out of hand.

Does “nice guy with an edge” exist? Where do I find him?
Don’t look for a nice guy. Look for a good man. And what the fuck is an edge? Seriously. Do you want him to ride motorcycles? Do you want him to slap you around a little in bed? Do you want him to be an unpredictable asshole because you’re bored easily and crave chaos? Shit, I don’t know what you’re into. Figure yourself out first and then come at me with something other than a meaningless cliché.

With all this talk of cities, may I ask what you think of Montreal? And what do you think it would take to make a move from Chicago to Montreal not a completely stupid idea?
Okay, first of all, why would you move to a French speaking city that isn’t Paris? Second of all, why would you leave Chicago for a place where the weather is even shittier? Third of all, if you’re gonna move to Canada, why wouldn’t you live in either Toronto or Vancouver? I mean, Montreal? Okay. You must have your reasons, but I don’t know what you want me to tell you.

Was I more lovable when I was skinny?
No, no, no. Stop thinking like that. The moment you equate your conformity to conventional beauty standards with your worthiness of love, you are well and truly fucked.

If you were out hunting and your shot happened to accidentally and unfortunately hit somebody in the face, who would you rather have as the recipient: Dick Cheney or Karl Rove?
Cheney. That’s not even a hard question.

I’m not a fan of republicans and I don’t like Jeb Bush, so why do I feel sorry for him?
Because he’s a sad little goober, and you’re very empathetic.

Bernie or Hillary? Why?
Because the alternatives are Trump or Cruz.

wait so *are* you advocating voting for hillary to keep a republican out of the white house? please go on.
Of course I am. I’m voting for Bernie in the primaries, but I’m happy to vote for Hillary in the general if/when she gets the nomination. It’s not just to keep a Republican out of the White House. Hillary is more qualified to be an American President than any other candidate in this entire election cycle. I like Bernie’s ideas better, but Hillary is a fucking boss. She would do an amazing job.

How much sexual harassment warrants pepper spraying an individual? I get harassed often on my walk home. From the routine “show me your pretty smile” to the occasional wish of anal rape. My fear is that in pepper spraying someone that is making me feel threatened that I will end up with an assault charge. What is the best way to go about ensuring my safety when using pepper spray?
Pepper spray is a weapon of self defense. Never use it as a retaliation to verbal street harassment. Feeling threatened is not the same thing as being in fear of imminent bodily harm. You’d better know the difference, because if you use pepper spray on a dude, one of you has committed assault, and if it wasn’t him assaulting you first, you’re fucked.*

*So if someone put their hand up my skirt, or grabbed my boob, could I mace them in the face then? Because for me that constitutes bodily harm.
Yes, absolutely. If someone deliberately makes harmful or offensive physical contact with you (especially if it’s sexual), that’s assault. You can totally mace a dude if he’s grabbing your boob or has his hand up your skirt. That constitutes self-defense. What you can’t do is chase the guy down when he runs away or find him later and then mace him. That’s no longer self-defense.

Why do people hate Hilary Clinton so much?
Because she’s a woman. If she were the exact same candidate, but a man, she would be respected by those who currently hate her. (Except for the folks who hate her from the far left because of her corporate centrism and war record, but those are the same type assholes who got George W. Bush elected by voting for Ralph Nader in 2000.)

I’m 26 and I have to get the hell out of the bay area. Somewhere less expensive with lots of green things. Suggestions?
For some reason, I feel like Asheville, North Carolina would be the perfect place for you. If you need a bigger city than that, go with Nashville. If you wanna stay West of the Rockies, go with Portland. Maybe also consider Denver, Austin, and New Orleans.

I’m finally on the right dosage of meds and seeing a therapist and a psychiatrist. I’m MUCH better, but I still lose some hours to panic and despair. Even with the klonopin. Is this just how it’s going to be forever? What the fuck do I do?
No, this is not how it’s going to be forever. It will take time, and I know right now you can’t tell the difference between a couple years and forever, but I promise, if you keep putting in the work, you will keep getting better.

You can’t just say you want a starmate after your history of shooting down everyone who yearns to have one such person. Maybe that’s karma for you.
A) That’s not how karma works. B) I don’t shoot down people who want to be in love. I shoot down people who believe in romantic destiny. C) I can say whatever I want. For instance, go fuck yourself.

Why can’t I help but feel that billionaires are better than me?
Because you think they earned it.

Where do your authority issues come from?
My authority issues come from consistently being wiser and having more integrity than those in authority.

Senpai notice me.
Hai.

How do the most toxic people still manage to have friends and admirers?
What’s toxic to you may be a drug for someone else. You’d be amazed at how many people crave poison.

People often wonder what the meaning of life is, the point of existence. There is none. So what’s wrong with committing suicide? It’s just skipping to the inevitable end anyway.
A meaningless existence is almost always preferable to a meaningless annihilation, and inevitability is the absolute worst reason to skip to the end.

How do you deal with the loneliness of seeing your close friends get married when you choose to be single? I’m worried that our lives will become too different and we’ll drift apart.
I wish I could tell you otherwise, but that’s exactly what will happen unless you, as the single person, put a lopsided amount of effort into maintaining the friendship. It sucks, but that’s life.

I want to cut my hair short, get tattoos down my back, quit my job, travel the world for a few months. I can’t stop thinking about death. I’m scared, but I don’t know why. Nothing about my routine changed but everything around me and inside me is starting to look different. What the fuck is happening?
Welcome to your first existential crisis. Cutting your hair and quitting your job to travel are perfectly fine, but I’d recommend not getting any tattoos until you’re on the other side. (You’ll know what I mean once you get there.)

Should I get an MFA in English first or just move to LA and try to make it as a TV writer with a BA in Psychology?
If your goal is to be a TV writer, absolutely do not get an MFA in English. Immediately move to LA and (if you must) get an MFA in screenwriting. (If you get into USC, it might even be worth it.) Start pounding out scripts, get good at pitching, and prepare yourself for a life of rejection and instability.

How much “ass-sucking” is too much when writing a cover letter for a part-time job?
Any amount is too much. Just be cordial. Make cover letters as short as possible. Introduce yourself, ask for an interview, and sign the fuck off. Let your resume do the talking.

How do you tell the difference between someone who just talks about enlightenment and someone who’s actually experienced it?
If you’re in a position where you need to tell the difference, that should be an indication in and of itself.

Has doing Dear Coquette affected your life in any way?
Profoundly.

There are days I think I’ll have been a success if I get off this planet without killing anyone. I don’t know what my question is. I don’t know what I want you to say. I just needed to get that out.
Your standards are a bit low. As for your question, what you’re really asking is, “Why am I filled with so much anger?” I don’t know the specific answer in your case, but I can say for sure that you’ll have been a success if you get off this planet having come to terms with the source of that anger.

Married. Children. Crush/in love with someone else that I can never be with. More depressed than I’ve ever been. Losing my mind. Selfishly sending you this because you have to read it and I cant tell anyone else. I don’t have a question. Sorry.
You desperately need a therapist, preferably the type who specializes in relationships, like an MFT, or a couples counselor who also takes on individual clients. Go do that for yourself. I know you think you’re a piece of shit, but you’re not. You need someone to talk to, and you really do deserve some help.

I’m in my last quarter of college and single for the first time in my adult life. Currently weighing two dudes and want your recommendation for this life stage: seriously hot asshole with a big dick or stellar personality guy with a small one?
Both. I’m totally serious. Not only can you date both. You should date both, especially if this is your last quarter of college. Don’t try and boyfriend-up a few months before graduation. That’s a recipe for bad decisions.

Can people go through completely life-altering events like the death of a loved one and still be materialistic or superficial? Can people reach enlightenment without facing a metaphorical or physical death?
First question: very easily, yes. Second question: no, because enlightenment is itself a certain kind of death.

What are your thoughts on how the presidential race is shaping up? And do you think Cruz or Trump is scarier?
Cruz is much, much scarier. I would honestly rather have Trump as president, if but for no other reason than (and I know this sounds crazy) his Supreme Court nominees wouldn’t be bible-banging wingnut conservatives.

What was the first album you bought?
Little Earthquakes by Tori Amos. I remember being so excited that I showed it to my piano teacher. I wanted to learn how to play some of the songs, but he scolded me for listening to music that was too adult for my ears. I stopped taking piano lessons shortly thereafter.