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.”