#126: Every question I’ve ever answered

& a Maybe Baby holiday special

Good morning!

Typically I take the month of December off, but this year I decided to spend the first two weeks putting together some year-end roundups. Last week was a list of my favorite things of 2022, and today I’m sharing a catalog of every question I’ve ever answered for my Dear Baby advice column (tell me why this took me literal days…). Tuesday will be a list of every product I’ve asked and received recommendations for (I’m always searching for/losing them). Friday will be every book I read this year, with various rankings. And on December 18th, my (our?) holiday break will commence and I’ll see you again on January 1st.

Re: Today’s list. I’ve answered more than 100 questions since I launched Dear Baby in June 2020. This catalog features 120 of them across 12 themes: work, friends, existential, love, New York, politics, mental health, womanhood, writing, and wildcard. I only left out a handful from when I did speed-rounds, because I wanted this list to collate my real, longform Q&As. I’ve wanted a list like this for my own personal use for a while, to reference what I’ve already answered on a given topic, and I hope it will be useful for you too, for the same reason. I plan to update it every month going forward!

Fair warning to my free subscribers that most of these Q&As are behind a paywall. That’s because my advice column is a paid perk that goes out on the last Sunday of every month. But I do often send a free preview, which is why 22 of the below questions are available to read for free (those are the bolded ones). It was mildly scary to go back and look at some of the older questions. Cringed a little and also felt like I could answer some of them better now, but I take that all as a good sign, and I hope it demonstrates what I’ve said in some of my answers about moving forward in spite of yourself. I stand by most of them!

If you’d ever like to write in, you can do so here, or call into my advice podcast I host with my friend Danny at 802-404-BABY. We’ve answered so many more questions there that aren’t reflected in this list! If you’re a free subscriber and would like to gain access to those episodes, along with my advice column, other podcasts, and weekly recommendations (including all the archives), I’m running a little holiday discount: If you sign up in December you’ll get 20% off your first year (that’s $40 for the year or $3.33333333333333 per month). Paying subscribers keep this newsletter running/me living and I’m so grateful for the support.

Also sorry in advance if this email gets cut off at the very end. I got scolded by the system for how long it is…cowards! But you can click to view the full thing on your browser if your heart is so called.

Work problems

• How did you come to accept that you were ready for a major career change?

• How has learning about workism changed your relationship to work, career, ambition? 

• Do you have any advice on how to start building my confidence back after getting fired?

• After 5 years in HR, do you have any behind-the-scenes secrets to share?

• How do you work through job disappointment and rejection?

• I followed my dreams and hated it. Now I’ve lost a dream and part of my identity. What should I do?

• I have no driving passions in life. What do you do when you have no clue what you want to do?

• All my older siblings are successful teachers and I failed at it. How do I stop feeling so deficient?

• Can you talk about the feeling of 'it's too late?’ I just turned 30 and haven't achieved 'success' yet.

• Should I finally give up my music career?

Friend issues

• How do you deal with a friend who lacks intellectual curiosity?

• Why does it feel like everyone has a cohesive friend group except me?

• Can I skip going to my old friends' weddings? I'm asexual and spending a day celebrating heteronormative love sounds terrible.

• My friend is uncomfortable with how much I gossip, but I'm fine with it. How do I proceed?

• How do you navigate (really, really) not liking the person your friend is dating?

• Do you have any advice regarding being fun versus standing up for what you believe in?

Existential dramas

Life decisions

• Should I move home to “reset”?

• Is the urge I have to uproot my stable life reason enough to do it, potentially disrupting the lives of those close to me?

• What are your thoughts on making big life changes during moments of uncertainty?

• How do you draw the line between thinking deeply about something and overthinking something?

• What are your thoughts on tattoos? Am I taking it too seriously?

Growing

• What was life like for you immediately after completing your time in school?

• Tips for having a great 30th birthday?

• Gaining insight on the stupidity of my younger self has made me afraid to make decisions, because what if I'm still stupid and just don’t know it?

• How do you allow yourself to grow, free of ego, and also forgive your former self for being dumb?

• What does it mean to ‘like yourself’?

• Am I delusional for expecting my life to be enchanting?

Looking ahead

• Is there a way to be a fully actualized adult AND be a parent?

• Thoughts on bringing babies into a world that is decreasingly hospitable to humanity? And my evolution on that thinking: How am I supposed to plan my future with climate catastrophe?

• What happens to us when we die?

Love & romance

Breakups and exes

• Why can't I stop internet-stalking my partner's ex?

• When is it a good idea to get back with an ex?

• I'm content with my breakup, so why am I obsessed with spying on my ex’s new girlfriend?

• My partner's friendship with his ex bugs me. Should I be more open-minded?

• How can I find peace as the one who was dumped?

Long-term love

• Do I find my partner attractive enough?

• When do you know someone is ‘the one’ to commit to?

• What advice do you have for a couple about to move into a one-bedroom together?

• What are your thoughts on infidelity in long-term relationships?

• Is it possible to maintain passion in long-term relationships?

• How do you and Avi navigate your differences, big and small?

• Advice on how to allow your partner to enjoy things you don’t? (I hate their cologne.)

• How do I accept my partner's lack of sexual interest while respecting my own needs?

• Should I tell my husband I'm bisexual?

• Can I ask my boyfriend to raise his living standards?

Can this be saved?

• Is my “gut feeling” to leave a good instinct of self-sabotage?

• What’s your opinion on different political leanings in relationships?

• Can people in a relationship just be ‘wrong’ for each other?

• Is it a red flag that 'future talk' makes my partner anxious?

• Do I criticize my partner because I love him and want the best for him, or do I not love him as much as I think I do?

• I love my boyfriend deeply but the sex is awful, what should I do?

• How do I know the love I feel for my partner isn't just a product of the familiarity?

Grab bag

• Can women to see themselves as feminist and progressive whilst expecting chivalry in a more traditional sense?

• Is there a way to heal and talk about my boyfriend's past cruel behavior without making my friends and family hate him?

• My boyfriend got another girl pregnant. Should I leave him? We're open and it was an accident. 

• I hate how my fiance baby-talks to our dog. How can I nicely ask him to stop?

• How should I handle my boyfriend feeling a little weird about my male friend?

• I'm happily married but still dream about an old crush. How do I move on?

• My boyfriend has taken up vaping and I hate it. What's the move here?

• Should we cave on our policy and let my partner's anti-vax parents attend our wedding?

• My boyfriend isn’t ambitious about money and I am. How do we reconcile this?

New York-based

• What's it like to move to New York without knowing many people?

• What do you love the most and hate the most about living in NYC?

• I have terrible New York FOMO despite not even wanting to live there. Thoughts?

• Did you ever feel like you weren’t cool enough to live in New York? Did you ever feel friendless?

• Why do we feel like proximity to celebrity makes us ‘better’?

• I'm 30, single, and moving to New York for grad school. Any advice about where to live?

Vaguely political questions

• What role do aesthetics play under capitalism?

• How do you deal with overconsumption of goods?

• What are your views on woke culture?

• How do you square your concerns about the internet with your usage of it?

• How do you square your consumerism with your critiques of late capitalism?

• What are your thoughts on the AOC Met Gala "eat the rich" dress fiasco?

• I’m debating getting married. What went into your decision not to?

Mental health

• How did you decide that therapy was the right choice for you?

• What if I’m stuck being depressed? When will I stop using it as an excuse?

• Is therapy a tool of capitalism, pushing us ever towards self-improvement and increased productivity?

• I feel guilty about how much weed I smoke. How much substance consumption is a good balance?

• How do you strike the balance between being vulnerable with someone and not trauma dumping?

Questions re: womanhood

Image

• What are your thoughts on the [gender] fluidity of style?

• How do you handle a discrepancy between what you know to be true (body acceptance, etc) and how you actually feel about yourself?

• How do you handle growing out your body hair?

• What went into your decision to forgo makeup?

• Am I wrong to be annoyed at people who get cosmetic work done?

Motherhood

• I'm having a kid unexpectedly and I'm afraid of losing my independent creative self, any advice?

• I feel like I’m not allowed to talk about how easy having a baby is for me without sounding like I’m invalidating other mothers' experience. How do I navigate this?

• My husband thinks kids will bring meaning to our lives, I'm afraid they'll do the opposite. How do we navigate this?

• How I manage the double-guilt of being a working mother: Not quite excelling in either role?

Writing, etc

Emotionally speaking

• When did you notice you were confident enough to keep going with your newsletter?

• How can I trust my work matters?

• How do you write about negative experiences you’ve had with people without them being offended?

• Lately I cannot make myself just sit down and write. I used to be better. How do I get past this?

• Why do you think nuance doesn’t translate well in online writing?

• How do you resolve to publish writing when you know you may change your mind?

Practically speaking

• How do you deal with difficult writing days?

• Any advice for new writers on how to edit their work?

• How do you find all the great stuff you read?

• What's your process for writing regularly?

• How did you picture your life as a freelancer and how is it different from your current situation?

• Any advice for successful pitches without having a long list of flashy bylines?

• What is your writing schedule like?

Wildcard & personal questions

• What are your thoughts on everything that went down at Man Repeller in June?

• I’d love to hear you reflect on pet ownership. How does Bug enrich your life?

• My mom won't stop sending me her Wordle scores and I'm pretty sure she's cheating. What do I do?!

• How often do you think about yourself in relation to who you were as a child?

• Did you have any serious hesitations about becoming a public figure?

• What fashion trends have you been into that in hindsight you wish you'd skipped?

• Is it normal to feel lost re: managing money? Any tips and tricks?

• What was it like to go from being a regular person to an influencer?

• What are some habits you’ve formed that have made you a composed adult?

• What books have you read lately that’s left an impression on you?

• What’s your favorite vacation or trip so far and why?

• What are your favorite ‘comfort movies,’ ‘comfort shows,’ and ‘comfort food’?

• What did you love and hate about living in SF?

• How do you feel about being followed by the types of people who follow you?

• May I ask which turntable you ended up going with?

• Can you share your religion/faith/spirituality journey?

• What's the opening song of your podcast?

• You mention drugs pretty regularly in your writing, what’s your relationship with them?

• What do you do now that you’re off Instagram?

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One more time for the Maybe Baby 20% holiday special:

Thank you so much for reading and asking this year :’)
Haley