Leandra Medine, the author behind hit fashion blog The Man Repeller, has made a writing career by carefully walking the line that separates personal anecdote from TMI.

Since she began the blog in 2010, she has spoken openly about her “sartorially offensive” style of writing—as well as private experiences that leave audiences cringing, such as detailed descriptions of at-home bikini waxes. There’s no topic Medine won’t discuss: she coined phrases like “arm party” and frequently causes readers to either gag or laugh out loud—or some combination of the two. The fashion world has responded with praise of Medine’s sense of humor and sharp intellect, leading the site, which was named one of the 25 best blogs of 2012 by Time magazine, to garner 1.5 million unique page views per month.

Medine also landed on Forbes’s list of “Top 30 Under 30” most influential trendsetters of 2012, a major feat for, at the time, a recent college grad still living with her parents. But in the end, it doesn’t matter how repelled one may be by Medine; it’s undeniable that she has assisted in pioneering a new generation of unapologetic, overall-wearing women.

Medine’s first memoir, Man Repeller: Seeking Love, Finding Overalls, out September 10, is equally as bold as her blog, if not more. The book is a mixture of work and play, chronicling every momentous occasion in Medine’s life, from getting her period for the first time to allegedly vomiting in her grandmother’s Hermès purse. By the end, readers will have learned about almost every bowel movement since Medine’s first day in kindergarten (and a little something about fashion, too). The memoir provides readers with a look into Medine’s personal life, which is essential in understanding her outrageously unique style. Ultimately, her memoir is about being a woman, falling in love (with both men and fashion), and growing up.

In honor of Medine’s bold subjects and information overshares, a look at the 15 most cringeworthy, man-repelling moments of the memoir:

1. What She Got From Her First Kiss: Chickenpox (the herpes of kindergarten).

2. Amount of Weight Gained at Summer Camp: 30 pounds—the combined result of hating camp and of receiving way too much food from her parents.

3. Details of Her First (and Only) “Suicide Note”: Written in the chapter on Mesopotamia in her middle school history textbook, Medine professed her life frustration: “If you’re wondering what’s happened to me, this region, this textbook, an exam on Monday forced me to jump out the window you will find open to your left.”

4. Reasons Why She Almost Got Kicked Out of Prep School: Happened on two separate occasions. First, for asking her mother what Dolce & Gabbana was. “To me, it sounded like a dessert—[my mother] turned white in the face.” Second, for wearing a crop top. “You must stop baring your midriff,” scolded her headmistress. “This is not a circus.”

5. Excuses on Why It Was OK to Not Have a Boyfriend: For a high school English project freshman year, a very single Medine compiled a list of why having a boyfriend was stupid: “The phone makes my ear hot,” “I want to be asleep by ten o’clock,” “We’re too young to have sex,” and “I’m not going to marry you so why waste my time.”

6. What She Said During her Internship Interview at Valentino: Medine asked her interviewer, “Can I use your discount?” Not quite sure how she landed the position, but she did.

7. Where She Met Her Husband: At a Halloween party in Chelsea. She was 17 and dressed as a flight attendant—think cheap polyester and way too little fabric.

8. Her AOL Screen Name : Cold Pencil, after the Red Hot Chili Peppers’ song “Warm Tape.”

9. What She Yelled When She Lost Her Virginity: “I forgot to take off my socks!” She was 19 and somehow didn’t scare her partner off—she’s now married to him.

10. What She Wore When She First Got Her Period: At age 13 and in math class, Medine was wearing her friend's “fancy-ass” Juicy Couture corduroy jacket when she first sailed the crimson wave. Her friend refused to take the jacket back, “even after it had been thoroughly washed, twice.”

11. Her Worst Period Experience: While giving a talk about The Man Repeller at Milk Studios during college, Medine got her period while on stage. Thankfully, she was wearing red suede pants. She decided to skip class and go straight home, resulting in the punishment of having to explain to the whole class in 500 words why she was absent. Naturally, she spared no detail.

12. Her Grandmother’s Opinion on “Jorts”: When she visited her grandmother at the hospital (who was admitted for contracting pneumonia) she told Leandra, “Darling, I know we’re in a recession, but surely your father can afford to buy you shorts without holes in them.” Her grandmother then kicked her out of the hospital.

13. How She Ruined Her White Suede Jimmy Choos: By stepping in dog poop. She may have lost a pair of shoes, but she gained an inevitable comparison to Carrie Bradshaw.

14. How She Solved an “Atomic Wedgie” at Her Wedding: She switched underwear with her mom. (Her mom, unlike Leandra, who was wearing her usual high-waist cotton granny panties, was wearing a burgundy silk G-string with black lace.)

15. Her Regular Bedtime Attire: Her retainer.