Transcript

A (0:00)

All right, y', all, gather round. Because Monet X change from sibling rivalry is here with an announcement. This episode of the podcast is brought to you by Google Gemini. Now listen, the girls over at Google said Monet, tell the children. So I'm telling you, us college students. Get Google Gemini's pro plan free for one year. Use the best model in the world for multimodal understanding. So whether you're uploading a video to get feedback on your presentation, uploading a photo of your homework to ask for help, or transcribing notes from a lecture you missed, Gemini 3 Pro can help. And baby, if I had this in college, oh, she would have been unstoppable. Picture it. Monet X changed in the library. Uploading picture of my music theory homework. Like Gemini, please help a diva out. Or recording my rehearsal videos for feedback instead of crying in the practice room for three hours. This would have been life changing. Now back to the goods. Sign up to get more access to Google's Most accurate model, Gemini 3 Pro. Unlimited image uploads, pro level image editing, higher limits in NotebookLM, Gemini in Gmail and Docs. Two terabytes of storage and more. You heard me, two terabytes. That's enough space to store every vocal warmup, drag race look, and every photo your aunt sends you of her plants. Visit Gemini Google students to learn more and sign up. Terms apply.

B (1:24)

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C (1:54)

Close your eyes.

B (1:55)

Exhale. Feel your body relax and let go.

C (1:58)

Of whatever you're carrying today.

B (2:01)

Well, I'm letting go of the worry that I wouldn't get my new contacts in time for this class. I got them delivered free from 1-800-contacts. Oh, my gosh, they're so fast.

C (2:09)

And breathe.

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C (2:21)

Summary

Not This Again with Bobbi Althoff

Episode: Teddy Swims "Lil Wayne changed my life"
Date: December 10, 2025
Host: Bobbi Althoff
Guest: Teddy Swims (Jayton Dimmesdale)

Episode Overview

This episode dives into the candid, offbeat, and revealing conversation between host Bobbi Althoff and singer-songwriter Teddy Swims. With characteristic awkward humor, Bobbi explores Teddy's rise to fame, personal history, self-perceptions, relationships, new fatherhood, music industry experiences, and internet culture—sprinkled with tangents about body image, strange DMs, tattoos, family, and social anxieties. The result is a vibrant, very human portrait of Teddy Swims, whose authenticity and self-deprecation match Bobbi’s signature style.

Key Discussion Points and Insights

Origins: From Street Singing to Stardom

[04:14 – 05:36]

Social Media Beginnings:
Teddy started by uploading covers to YouTube in 2019 and singing "everywhere," including with buskers on the street:

“We would just find buskers and… roll up on them and say what’s up and sing.” (Teddy, 05:17)
Defining “Busker”:
Bobbi confesses she’d never heard the term; Teddy explains it’s a person who performs music in public places for tips.

The Teddy Swims Name

[06:31 – 08:49]

Real Name: Jayton Dimmesdale.
Nickname Origin: Called “Teddy” as a child because:

“I was like a little fat kid. It just kind of stuck.” (Teddy, 06:55)
SWIMS Meaning:
Teddy jokes about the SWIMS acronym—both “Someone Who Isn’t Me Sometimes” and “Someone Who I Massage Sexually,” poking fun at his indecisiveness about its real meaning:

“Originally, this started as like a rap project… and then it just stuck as Teddy Swims.” (Teddy, 08:14)

Economic Realities and Upbringing

[10:46 – 13:56]

Financial Status:
Teddy doesn’t consider himself rich despite his success, noting the expenses and responsibilities that grow with fame.
Humble Beginnings:
Describes growing up without money, boiling water for baths:

“My dad spent a lot of time fighting for lights and water… he’s the best human being in the world.” (Teddy, 12:29)

Body Image, Confidence, and Appearance

[17:19 – 24:57]

Acne and Beards:
Teddy’s never had acne, but jokes that his beard is like makeup for men. He discusses rumors about baldness—denies any hair transplant; he grew his hair by choice and even has head tattoos.
Ratings and Confidence:
Teddy rates himself a confident “10” on superficial looks:

“Yeah. I’m cool.” (Teddy, 23:24)
Bobbi pokes fun at the double standard, saying women often rate themselves much lower.
Tattoos:
Teddy is ~90% covered in tattoos, including eyelid ink, inspired by Lil Wayne:

“I’m a huge Lil Wayne fan and Carter 3 changed my life… I gotta get my eyelids tattooed.” (Teddy, 21:56)

Lil Wayne’s Impact

[21:54 – 22:28]

Direct Inspiration:
Teddy shares that Lil Wayne’s Carter 3 album and “fear of God” eyelid tattoos motivated his own eyelid tattoos, marking a key moment in his artistic development.

Family, Fatherhood, and Partnership

[25:32 – 29:07]

Love Life:
Teddy’s been with his girlfriend for about a year and a half; their relationship moved rapidly, and they’re now parents to a 3-month-old son.
Home Birth Story:
Praises his partner for delivering their baby at home:

“She’s a fucking superhero. We bought a house in Nashville and she did this thing, man, it was so amazing.” (Teddy, 27:52)
Reflections on Parenthood:
Expresses deep love for his child and stress typical for new parents; he admits to crying daily about his son.

Thoughts on Internet Culture & Hate Comments

[32:11 – 33:12]

Teddy's Internet Nicknames:
Recites a list of fat jokes and celebrity comparisons (e.g., “Jake Paul let himself go,” “Snack Miller,” “Toast Malone”), finding them more amusing than hurtful.
Bobbi on Her Haters:
Notes she gets racist, angry hate comments, mostly from a very specific demographic.

Personal Insecurities and Social Anxiety

[45:03 – 46:24]

Teddy’s Insecurities:
He feels socially awkward and tends to overthink, sometimes feeling out of place.

“Sometimes I just overthink things a little much… I feel like I don’t belong sometimes.” (Teddy, 45:49)
He also grew up insecure about his body, particularly his weight and moles, but now has embraced them as part of who he is.

Celebrity Encounters: Justin Bieber

[34:50 – 38:30]

Quirky DMs:
Shares a bizarre Instagram DM “hand video” from Justin Bieber, which sparked a running joke of Teddy sending similar hand videos back (unanswered).

“So now every time I see little hand videos, I just send it… he just leaves me on scene. But he started it!” (Teddy, 36:50)

Marriage, Kay Jewelers, and Brand Collabs

[30:09 – 32:00]

Proposal Plans:
Discusses future engagement; jokes about asking jewelry sponsors for a ring.
Brand Collaborations:
Reveals collaboration with Kay Jewelers on modern pieces, pushing against the brand’s “for old ladies” stereotype.

Parenting Styles: Co-Sleeping and Breastfeeding

[39:48 – 44:34]

Co-Sleeping:
Defends co-sleeping with his infant, noting natural parenting choices and critiquing external judgment:

“I love my baby… I’m close sleeping with my son. I’m sorry, man. Y’all can… you don’t like it, lump it, buddy.” (Teddy, 41:54)
Extended Breastfeeding:
Supports “weird” parenting habits like extended breastfeeding; jokes about “co-nursing.”

Light-Hearted Tangents & Fun Moments

[17:19 – 44:34, various]

Face, Beard, and Bangs:
Bobbi and Teddy muse about physical features, hair, and “bangs regret.”
Tattoo Meanings:
Eyelid and facial tattoos, inspired by Lil Wayne and Nelly (with the face Band-Aid).
Breast Milk Taste Tests:
Bobbi asks if Teddy's tried his partner’s breast milk (“Yeah, totally. It’s actually quite sweet.” [Teddy, 44:25]).

Notable Quotes and Memorable Moments

On self-acceptance:
“Yeah. I’m cool.” (Teddy on rating himself, 23:24)
On celebrity inspiration:
“Carter 3 changed my life… I gotta get my eyelids tattooed.” (Teddy on Lil Wayne, 21:56)
On co-sleeping controversy:
“If somebody’s baby’s happy and healthy… I need to hear it from the guy who killed his baby.” (Teddy, 41:39)
On Justin Bieber’s “hand video” DM:
“[Justin] sent me this weird hand video… so every now and then, I see some weird hand video and I just send him them. He just leaves me on read. But he started it!” (Teddy, 36:50)
On growing up poor:
“Spent a lot of time fighting for lights and water… he’s the best human being in the world.” (Teddy about his father, 12:29)

Timestamps of Key Segments

[04:14] – Origins and street singing
[06:31] – Meaning and origin of the name “Teddy Swims”
[10:46] – Financial realities and upbringing
[17:19] – Appearance, beards, body image
[21:54] – Tattoos inspired by Lil Wayne
[25:32] – Relationship, becoming a parent, home birth
[32:11] – “Fat guy” internet jokes; reading hateful vs. amusing comments
[34:50] – Story about weird DMs from Justin Bieber
[39:48] – Parenting styles: co-sleeping and opinions about it
[45:03] – Insecurities, social anxiety, body image
[47:44] – Fake names and signing autographs for resellers
[49:23] – Wrap up and closing remarks

Tone and Style

Bobbi Althoff’s signature deadpan, self-deprecating humor, peppered with abrupt, unexpected questions and playful jabs.
Teddy Swims is open, warm, humorous, and sincere—unfiltered but reflective, with moments of accidental profundity.
The tone is irreverent, candid, and at times, absurd—never shying from awkwardness or sincerity.

For Listeners: Why This Episode Stands Out

This episode highlights not only Teddy Swims’ musical journey and creative influences but also offers a rare, intimate look at his values, humor, and struggles. Bobbi’s unique interviewing style creates space for both laughter and honesty about friendship, self-worth, family, and the realities of online and public life. The show's best moments come from their unscripted, genuine exchanges—the very "awkward conversations you won’t find anywhere else.”

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