Brutally Anna – Episode Summary

Episode: “Fertility Math Will Make You Crazy”

Host: Anna Kai
Date: October 24, 2025

Main Theme:

Anna Kai gets brutally honest about the messy, anxiety-inducing reality of trying to get pregnant in your mid-30s. With signature wit and vulnerability, she unpacks the unexpected emotional and logistical tolls of fertility “math,” the failures of sex education, shifting from avoiding pregnancy for years to desperately hoping for it, and the modern pressures on women to time their lives – and bodies – perfectly.

Key Discussion Points & Insights

1. Life Before Fertility Anxiety & Tracking

• Anna reminisces about her 20s, going through life with untracked periods. She didn’t worry because things “just sort of worked out.” Now, tracking is a big part of her life—especially after experiencing PMDD (Premenstrual Dysphoric Disorder).
• [03:20] Anna: “There was a time in my 20s when I had no idea when my period would come… I always assumed it would come and it always kind of did.”

2. Hormones, Mental Health & Preparation

• When she realized her mental health dipped prior to her period, Anna started tracking her cycle using Flow and discussed her symptoms with a psychiatrist.
• Her journey took her through Zoloft, Wellbutrin, “raw-dogging it,” and back to Zoloft—balancing mental health against the desire for pregnancy.
• She details how, ultimately, small changes—like eating breakfast, regular exercise, and (finally) taking vitamin D—helped stabilize her more than any single pill.
• [05:36] Anna: “Honestly, sometimes you just need the thought of being responsible for somebody else to be responsible for yourself...”

3. Decision to Try for a Baby

• Anna and her husband Dave decided to try for a child after three years of marriage, only when Anna felt “as ready as she’d ever be”—with Dave trusting her lead on timing.
• Anna expresses frustration when men say “we’re pregnant,” venting over how pregnancy is not equally shared physically or emotionally.
• [08:32] Anna: “Bro, unless you’re carrying half of the child, you’re not pregnant. Your wife’s pregnant. You had sex, had a really great time, and now you get to wash your hands of this for the next nine months.”

4. The Harsh Math of Fertility

• Anna describes the emotional whiplash: spending years doing everything possible to avoid pregnancy, only to later realize how incredibly difficult it can be to conceive.
• She laments that, for all the accidental pregnancies we heard about growing up, biology is “brutally inefficient”—with only 1-2 days per cycle being truly fertile, and even perfect timing yielding just about a 20% chance each month.
• [19:10] Anna: “The amount of people who get accidentally pregnant, it’s like, oh my god, you are actually so unlucky…there's only a 20% chance that you can get pregnant because it’s just that hard.”
• She openly shares her pee-cup method for ovulation tests, poking fun at the realities of fertility gadgets.

5. All the Ways Sex Ed Failed

• Anna points out that sex education, even in expensive college settings, focused on condoms-on-bananas and left her completely ignorant about her own anatomy, cycles, and the realities of conception.
• She argues that sex ed should be continuous and actually useful at the life stage when people need it most.
• [21:36] Anna: “When I first learned about the reproductive system, I was like 16, I was still a virgin…I don’t remember anything about my own anatomy. It’s just too foreign. Nothing really sticks with anybody until it’s relevant to them.”

6. The Frustration, Guilt, and Community of Trying

• As Anna details the exhausting (and often hilarious) schedule of timing sex, ovulation, and travel, she highlights just how unsexy and fraught the baby-making process really is.
• She sends compassion to anyone struggling, especially those navigating the anxiety of “natural” attempts, looming fertility treatments, and the whole ecosystem of unsolicited advice.
• [28:34] Anna: “For anybody listening, if you’ve had a really hard time getting pregnant, I now understand why it sucks so much.”

7. Social Pressures & Annoying Advice

• Anna critiques those who scold women for waiting until their 30s (“the optimal age is your early 20s!”) and is grateful for her choice, despite the struggle now.
• She resists the deluge of internet “advice” (e.g., Mucinex for fertility), shutting down armchair experts and emphasizing the importance of privacy in her journey.
• [36:08] Anna: “If you tell me to take Mucinex one more time, I’m going to scream. Like, I just can’t...I’m pretty sure if it did, my OBGYN would have told me that by now.”

8. A Note of Solidarity & Hope

• Anna ends by expressing deep gratitude for her friends and listeners who’ve shared their difficult journeys or eventual, hard-won success stories—those keep her going.
• She wants others in this boat to know: it’s okay to be messy, frustrated, or not find the process magical.
• [34:45] Anna: “Those are the most inspiring stories, and those are the only stories I really need to hear right now. I don’t need any advice. I really, really despise the amount of just absolute bullshit surrounding the topic of getting pregnant.”

Notable Quotes & Memorable Moments

• [08:32] Anna, on shared pregnancy:
  “Bro, unless you’re carrying half of the child, you’re not pregnant. Your wife’s pregnant. You had sex, had a really great time, and now you get to wash your hands of this for the next nine months.”

• [19:12] Anna, on the odds:
  “There’s only a 20% chance that you can get pregnant because it’s just that hard. So for the people who, like, accidentally get knocked up...you are a fertile nymph. Who are you?”

• [21:36] Anna, on sex ed:
  “When I first learned about the reproductive system, I was like 16, I was still a virgin...Nothing really sticks with anybody until it’s relevant to them.”

• [28:34] Anna, on solidarity:
  “For anybody listening, if you’ve had a really hard time getting pregnant, I now understand why it sucks so much.”

• [36:08] Anna, on unsolicited advice:
  “If you tell me to take Mucinex one more time, I’m going to scream. Like, I just can’t.”

Important Timestamps

• 03:20 – Anna discusses her “blissfully ignorant” 20s and the onset of PMDD
• 05:00 – Navigating mental health medications and choosing self-care
• 08:32 – On the realities of pregnancy for women vs men
• 13:00 – Getting “ready” for a baby and resisting outside pressure
• 19:10 – The math of fertility cycles & frustration with accidental pregnancy stories
• 21:36 – Rant about the failures of sex education
• 28:34 – Compassion and solidarity with others on the fertility journey
• 34:45 – Rejecting toxic advice and cherishing hopeful stories
• 36:08 – Pushback against fertility hacks and judgment

Tone & Takeaways

Anna’s signature is raw, comedic candor—she curses, self-deprecates, and leaves no vulnerability unturned. Her tone oscillates from biting sarcasm (“Bro, unless you’re carrying half of the child, you’re not pregnant”) to generous solidarity with listeners who feel “too much, think too hard, and talk to themselves in the shower.”

If you’re trying to conceive, considering it, or have felt pummeled by fertility expectations, Anna’s message is this:
You’re not alone in the mess, the math, the madness, or the agonizing wait. Go easy on yourself. Eat the sushi. And ignore anyone who tells you to take Mucinex.