anything goes with emma chamberlain
Episode: “wait idk how to flirt”
Date: December 18, 2025
Episode Overview
In this candid, introspective episode, Emma Chamberlain opens up about an age-old conundrum: flirting. From the comfort of her bed, Emma admits she has no clue how to initiate flirty interactions—despite being outgoing in other ways. Using a mix of storytelling, a live "flirting quiz," overthinking, and self-exploration, she examines why flirting is so intimidating for her, the roots of her fear, and whether mastering this “skill” is even possible. With her signature blend of humor, vulnerability, and overanalysis, Emma unravels not just her personal blockages about flirting, but the cultural and psychological hurdles many of us face.
Key Discussion Points & Insights
1. The Brain-Crush and the Fear of Initiation
[00:00-07:00]
- Emma describes her “tiny, brain-only crush” on a guy she sees regularly but has never spoken to:
- “This is a crush. So little that it will never leave the confines of my mind.” [00:20]
- She is too shy to even make eye contact, let alone talk to him.
- Wonders if it’s a red flag when a guy doesn’t initiate, but admits she can't make the first move either.
- Reveals her tendency to rely on men to make the first move and confronts her own aversion to putting herself out there.
2. The High School Trauma Root
[07:10-15:30]
- Emma traces her fear of rejection back to an awkward high school bonfire make-out, where she felt judged and abandoned.
- “I have never been the same from… Wait, this just got so deep.” [08:50]
- Acknowledges this event as a formative trauma underlying her fear of initiating romantic moves.
- Discusses her lack of confidence in her flirting skills—unless the other person is strongly leading.
3. Flirting Ability: The Online Quiz
[16:40-35:30]
- Emma decides to take an online flirting quiz to “test her baseline flirting ability”:
- Hilariously critiques classic pickup lines—finding most of them “cringe," but acknowledges she might sarcastically use “Is this seat taken? Do you want it to be?” [18:30]
- Admits that humor is her default mode, for better or worse.
- Recognizes her tendency to use friends as “wingmen” and how she leans on them as a crutch when flirting.
- Key honest admissions:
- She has “always had a crush” since childhood—“I love having a crush. I always have a crush. It's just who I am.” [27:10]
- She mostly flirts with people she knows a little, rarely strangers.
- Flirting style: notice small details, compliment, but worries about being “too cringe” or misreading signals.
- Quiz result: “You’ve got natural charm. You’re not a huge flirter, but you tend to charm the people you meet anyway. Sometimes you’re probably not even aware you’re doing it.” [34:30]
4. Overthinking: Barriers to Flirting
[35:40-41:00]
- Emma identifies the three main things blocking her from flirting: high school trauma, fear of rejection, and fear of coming off as creepy (“I overthink everything”).
- Realizes that self-work may be required before any tactical, step-by-step flirting advice can help.
5. Breaking Down WikiHow’s “How to Flirt” Guide
[41:10-01:10:30] Each step is read, humorously critiqued, and reflected upon by Emma as she applies it to her own fears and behaviors.
Flirting from Across the Room
- Make eye contact: Impossible for Emma, who admits to looking at the ground. [43:00]
- Smile: Notes she naturally smiles around crushes (“it's like, almost biological”). [45:10]
- Be mindful of body language: Realizes her tendency to cross arms out of nervousness.
- Plan run-ins: “I’m good at the plot, I can plan ahead… but once I’m in the moment, I’m looking at the floor.” [48:00]
- Look your best: Agrees this helps, but doesn’t fix the deeper issue.
Flirting In Person
- Start a conversation: Emma wrestles with worry about coming off as obviously trying to initiate, wants it all to feel “natural” (but wonders if this is an excuse).
- Smiling, laughing, breaking the touch barrier: She’s comfortable being friendly but draws the line at escalations like touching, unless cues are extremely clear.
- “Breaking the touch barrier, it sends a signal… but I’m nervous about it.” [57:15]
- Drawing attention to your body: Emma is candid about “imposter syndrome” with being sexy, despite being willing to wear a “sexy outfit.” [59:50]
- "I'm funny, and I'm silly, and I'm outgoing, and I'm playful... but I'm not sexy." [1:00:00]
- Dancing: “My biggest fear...doing it sober, it's possible, but it's tougher.” [1:01:15]
- Compliments and teasing: Emma is naturally complimentary and enjoys banter/teasing, both giving and receiving.
- Leaving him wanting more: She’s hyper-aware of overstaying her conversational welcome.
- “Like, I’m constantly giving people an out because I never want anyone to feel like, ‘Oh, my God, I’m talking to Emma and I don’t want to talk to Emma anymore.’” [1:06:40]
Flirting Over Text
- Emma feels much more confident here, since she can “phone a friend” and isn’t put on the spot. [1:10:40]
- Dislikes game-playing or overly cutesy/cliché texts: “If I want to text somebody, I want to do it with intention.” [1:12:10]
- Prefers texts with context from real life, not random fabricated banter.
- Suggestive texting makes her uncomfortable; would rather show attraction in person.
Notable Quotes & Memorable Moments
- “I can't make eye contact with a guy that I sort of, a little bit, have a crush on that I will never date... Like, if I can't make eye contact with a guy where there's no stakes. Like, obviously I can't make the first move with a guy where maybe there are stakes.” [03:40]
- “I have never been the same from. Wait, this just got so deep. No, but I have never been the same.” [08:50] (on her high school rejection trauma)
- “If somebody's flirting with me really hard, like, I'm there, I can show up, but they have to really be into me. I need it to be very clear.” [10:55]
- “It would be nice to feel confident in my flirting skills as an initiator, because who knows what shy, wonderful guys I'm missing out on because I'm too afraid to do a little flirt first and see what happens.” [11:30]
- “I need to start seeing myself as a sexy goddess, for one.” [1:18:50]
- “If I don't get a response [over text], I am done. We are never speaking again. Easy.” [1:16:20]
- “I want to talk to every guy that I want to talk to, and I don't want to have to rely on them talking to me first. So, if this is the price I must pay, I'll keep you all updated on my flirting journey.” [1:22:20]
- “2026. Emma's flirting. That's the end of it… Stay flirty. Bye.” [1:24:00]
Timestamps of Key Segments
- 00:00 – 07:00: “Tiny crush” confessions, fear of initiating
- 07:10 – 15:30: High school trauma origin story
- 16:40 – 35:30: Taking and discussing a “flirting ability” quiz
- 35:40 – 41:00: Overthinker’s barriers: trauma, rejection, being “creepy”
- 41:10 – 01:10:30: Testing and critiquing WikiHow steps (eye contact, smiling, body language, conversation, touch, being “sexy”)
- 1:10:40 – 1:20:00: Flirting over text: honesty vs. playing games, confidence in digital contexts
- 1:20:00 – 1:24:00: Final reflections, affirmations, and a toast to 2026 as “the year of flirting”
Tone and Takeaway
Emma’s trademark vulnerability, self-deprecating humor, and “overthink everything” honesty run through the entire episode.
- Listeners are taken on an inner journey—from the mortifying roots of flirtation fear, through practical and impractical advice, and finally toward a place of gentle self-acceptance and determination to improve.
- Her self-exploration is both deeply relatable and highly entertaining, mixing real admissions with jokes (“We’re going to need a colonoscopy to get that one out!” [1:00:45]).
- While Emma claims she didn’t learn how to flirt (yet), she ends with a challenge to herself and her audience: “2026. Emma’s flirting.”
For the Listener Who Hasn’t Heard the Episode
This episode is an insightful, funny, and thoroughly Emma exploration of what makes flirting so difficult—especially for those who feel confident in every other social arena. Emma provides a mirror for anyone who’s found themselves “looking at the floor” around a crush, and offers hope (with plenty of laughs) that with a bit of self-work and risk-taking, anything is possible—even mastering the art of the flirt.