I’m 33, single, newly unemployed and for the first time in my life able to say “fuck it” and do some extended, no-return-flight-booked traveling. Where would you go?
I could name a bunch of cities, but fuck that. As of tonight, it’s Springtime in the Northern Hemisphere and Autumn in the Southern Hemisphere. You know yourself. Pick your favorite season. Pick a place where you’ve always dreamed of having a love affair, and then just go.

If denial is drinking piss from a golden chalice, is acceptance drinking Dom Perignon from a party cup?
Yeah, okay. I can get behind that metaphor.

How do I accept the inevitable?
By realizing that it doesn’t matter whether you accept it or not.

What are your favorite movies about LA? I’ll be moving there next year and I’d like to imbue myself with the city beforehand.
LA Story, The Big Lebowski, Magnolia, Wonderland, Jackie Brown, Point Break, The Player, Clueless, Beverly Hills Cop, LA Confidential, Drive, Swingers, Kiss Kiss Bang Bang, and Boogie Nights.

I woke up naked next to my ex. How do I justify this?
It happens. No need for justification. (Just don’t make a habit of it.)

I’m 21 male and bored of sex and not attracted to anyone. HOW DO I GET MY DRIVE BACK?
Stop watching porn. (Give it at least a month. If you don’t notice a difference, hit me up in the comments and we’ll go from there.)

Do people generally submit enough concise questions for you to do a fun-sized advice post, or do you edit the questions to make them fun-sized?
I get a shit-ton of fun-sized questions. After all these years, my readers just kind of know the difference between fun-sized and regular sized, so there’s no need to edit them at all.

Are you addicted to anything?
Nope. Never have been, but with my history of decadence and drug use, it’s not really fair for me to take credit for that. I won the genetic/environmental lottery with regard to addiction. It’s just luck that I’m not predisposed to addictive behavior, and I know that about myself.

How many books do you own?
Dude. That’s kind of like asking how many people I’ve slept with. (I honestly have no idea, but it’s a lot.)

Why am I constantly looking for a husband?
Because that’s what you’ve been programmed to do.

What if I don’t find someone to spend my life with?
Share your life. Don’t spend it. Quit worrying about the what-ifs.

I burned all my bridges. I cry all the time. I don’t believe in self-love.
Sounds like a good place to start. (I’m not kidding. You’ve burned it all down and wrung yourself out. Now comes the change, the whole “rising from the ashes” part. Step out into some new shit. It’s time for what’s next. It’ll be scary, but you can do it.)

Just had amazing sex four times in less than 24 hours. A couple years ago I was sending you messages at 4 in the morning, crying and tortured about my experiences with sexual violence. Life can be good.
Yes it can. (And for all of you out there who are crying and tortured, just know that this can be you too. A couple years may seem like forever, but it’s not. Healing takes time, but shit really does get better.)

I recently realised that my entire identity and existence is based on/revolves around other people’s opinions on my worth, and buying shit to try and keep up with this. Like, the whole thing, and a constant inner monologue berating myself for not achieving this bullshit standard. I’m disgusted with myself and want to change. What do I do?
Keep realizing it, every day, over and over again, until the realization itself becomes a part of your identity. Nurture a sense of your own self-worth. Develop some fresh self-respect. Let those traits become the voice of your new inner monologue, and I promise, the change will come.

If New York is just eight million people agreeing to be uncomfortable with each other for the privilege of living in New York, and LA is twenty different cities swirled together, each with half a million people, none of whom are aware that the others exist, what’s the Bay Area?
The Bay Area is five million people who secretly think they’re better than everyone in New York and LA.

What are your thoughts on Deray McKesson running for mayor of Baltimore?
I think he would make an excellent mayor, and I would urge all of my readers in Baltimore to vote for him.

Do you have any exes that you would consider getting back into a relationship with?
Nope. There are a few I’d fuck for old times sake, but none I would ever revisit emotionally.

What kind of writing do you like best?
The kind that teaches me.

What is your deepest flaw? The worst of your bad habits?
At my worst, I’m arrogant, and I have a tendency to self-sabotage.

At what age do guys learn to take care of themselves and get their shit together, because I’m twenty-one and all I see are twentysomething babies.
Unless life comes along and forces their hand, these days it typically doesn’t happen until their late thirties.

He loves baby talk. I can’t keep this up anymore. He’s great otherwise.
Yeah, this one’s easy. Enforce a zero tolerance policy on baby talk. Don’t put up with that annoying bullshit for a single second. Make it painful for him. You’ll be surprised how quickly his behavior changes when there are consequences.

Are all beauty standards cultural or are some grounded in biology?
Everything about the human condition is grounded in biology, including culture itself. We are animals, after all. We may be gifted with the cognitive ability to recognize our own social constructs, but that doesn’t change the fact that we’re a bunch of talking monkeys.

I’ve had a couple dreams that your identity has been revealed. Why is that?
Those dreams are about you. I’m guessing that you’ve got some kind of secret that’s causing you some anxiety.

So, I’ve got the job and the guy, the baby and the house are on their way. What now? Just stay the course?
Like you’ve got a choice.

Why do the Underwoods need a “Tom Yates” (or a “Meachum”) and what role does Tom particularly play for us viewers?
The Underwoods don’t have children. There’s just the two of them, and a dyad is an unstable relationship unit. They consistently need a third person to make their relationship unit a triad, which has a stabilizing effect. This is actually a real thing that happens. Most normal couples without children do this with a mutual friend, but the Underwoods aren’t a normal couple, so they have to carefully and mutually groom a third person to fill that role. For viewers, Tom’s role is that of an audience surrogate. He allows us to be a part of the Underwood relationship while still having a conscience.

Do you have a favorite character on The West Wing?
I always had a soft spot for Toby Ziegler.

My life is a fucking mess. We’re both intelligent people. You seem to have it together. How?
Dumb fucking luck.

What’s your Myers-Briggs personality type? I know it’s dumb but I’m so curious.
I’ve answered this question sarcastically in the past, but now that I’ve got a flourishing comments section, I’ll let you all take a few guesses before telling you. This should be fun.

Your advice has indirectly resulted in attempted suicide. So thanks for that.
We both know that’s not the way it works, indirectly or otherwise. Still, you felt the need to reach out, and I want you to know that I heard you. If you’d like to reach out again, please do. I’m here.

How do you get over the fear of abandonment?
Identify and then come to terms with the life events that formed your underlying fear of abandonment.

please make the screaming nightmare stop
I just spoke with Abraham Lincoln. He told me he’d visit you in your dreams and take care of business.

how do i break the cycle of abuse when i’m so in love
Stop using what you think is love as an excuse, have some fucking self-respect, and end the fucking relationship.

My best friend in the whole wide world just called me ecstatic, announcing that she is having twins with her boyfriend who just last month put her in the hospital. They’ve only been together about three months, but I know of at least 3 incidents of him hurting her. Right now she is over the moon… tell me there is way for me to get her out of this situation with minimum damage, please.
Nope. She’s fucked for life three times over, and there is absolutely nothing you can do about it. Sorry. (I mean, there’s an outside chance that he beats her into a miscarriage and goes to jail, but that’s pretty fucking dark for a best case scenario.)

I just had an abortion. Thank goodness this was an easily available option to me. I am so grateful.
Amen and fuck yeah.

Coke, I’m terrified.
Nah, you’re just anxious. There’s a difference.

Are some people worth more than others?
Yes.

Does it ever stop being complicated?
Yes.

Could anything be considered art?
No.

My friend posts pictures on Facebook and Instagram of herself doing yoga every damn day. Every fucking day. I introduced her to yoga and she took it further than I thought she would. I should be proud and happy but why does it just irritate me?
Because she is an asshole.

Best city in Arizona to live in?
Los Angeles.

What’s your favourite number from 1-100?
17

If New York is just eight million people agreeing to be uncomfortable with each other for the privilege of living in New York. What’s LA?
LA is twenty different cities swirled together, each with half a million people, none of whom are aware that the others exist.

I need something sarcastic and funny and a little bit meaningful until You’re The Worst comes back. What do I watch?
“Love” on Netflix. It’s not nearly as good as “You’re the Worst,” but Gillian Jacobs is amazing and it’ll get you where you need to go.

Okay, so, feel and embrace the raw pain of heartbreak. Feel it all the way to your core. How long do you allow yourself to feel that pain? What if I can’t stop feeling sorry for myself in addition?
Self-pity isn’t an emotion. It’s deliberate misdirection of emotion, a feedback loop that keeps you feeling the same pain over and over again. There are all kinds of reasons people hold on to negative shit, but the point is to feel your pain for as long as necessary in as little time as possible. The whole point is to let it go.

I’m so infatuated I want to cry every time he leaves.
Get your shit together.

Do you still get those moments of terror when you realize that you’ll have to die?
Sure, but now I can sit down next to those moments and smile.

Why do I focus all my energy on trying to keep him while recognizing that the things he does hurt me?
Because your threshold for pain is high enough to compensate for your fear of abandonment.

Isn’t having a “purpose” delusional? Life has no purpose other than what it is.

You’re confusing purpose with meaning.

I have so much going for me. Why do I want him to hate-fuck me?
What does one have to do with the other?

Do you own the DSM?
Of course I do. I consider it bathroom reading material.

Why’d you leave LA/CA?
Because I’d done it, and it was time to do something else.

I’ve been reading your sage advice for a long time, as most of us have. I’ve written to you once or twice, as most of us have. You’ve given pro-bono legal, psychiatric, financial, political, and romantic advice for a long time. Can you at least create a way for us to send you whiskey in return? (Without compromising your identity.)
You’re very thoughtful, and I appreciate the gesture, but how about you just raise a glass to me instead?

I’m empty. What do I fill myself with?
First, hope. Then some strength. After that, motivation. Then finally, purpose.

How do you fake being secure? I don’t have any idea on how to even fake not despising myself.
The trick isn’t to fake being secure. The trick is to embrace your insecurity. Part of that process is forgiving yourself and just letting it all be okay. (It’s not easy to do, but it’s a much better use of your energy than faking anything.)

Why does it bother me so much when he follows his apologies with “I didn’t intend to hurt you”?
Because he’s trying to excuse himself by invalidating your pain or he’s confessing that you were never supposed to find out in the first place. Either way, fuck his intentions. They don’t mean shit.

Does Walter White have narcissistic personality disorder?
More like antisocial personality disorder. (And how are you just now watching Breaking Bad?)

Lately when I’m almost asleep, I wake up suddenly, filled with shock and horror that I really, actually have to die someday.
Yeah. That’s a thing that happens. Terrifying, isn’t it?

I just had my heart broken for the first time and holy shit. I literally have chest pain. These chemicals surging through my body are the worst. What the fuck. Ow ow owwww make it stop.
Feel that shit. Feel it all the way deep down. Feel it hard. That exquisite pain is one of the most raw and uniquely human emotions you can experience, and someday it will be useful to you.

Why do our moms hate Hillary so much?
They’d never admit it, but the real reason is internalized misogyny.

Which is worse: being the dumbest person in the room, or the smartest person in the room?
Depends on the room.

Until you have the ‘let’s be exclusive’ talk, all’s fair in the dating wars, right?
Wrong. All is not fair, so it’s best you follow the golden rule: Do unto those you are dating as you would have them do unto you.

He’s never heard of Nick Cave. This is a dealbreaker, right? I mean, come on.
That’s not a dealbreaker. That’s an opportunity. (Don’t be a snob.)

What kind of drinks would you personally order at a dive bar and what would you order at a more upscale place?
Whiskey.