He agreed to it half asleep. Within ten minutes she has ruled on his tattoos, Kenda has called him every red flag there is, and he has explained that being six foot six makes it hard to hide. It gets sharper from there. He describes his playfulness and she tells him it does not sound like play, it sounds like strategy. He talks at her long enough that she stops listening, and says so out loud.

The turn comes when he brags about jokingly threatening to fight his boss's mother, and adds that she laughed. She is sitting right there. She did not laugh.

CHAPTERS
0:00 Getting set up
1:10 Meet Ann Whittington, psychotherapist of 35 years
1:56 "You need tools" / "What boundaries?"
3:05 Do bad tattoos count?
4:03 Every single red flag there is
6:45 It doesn't sound like play, it sounds like strategy
7:37 Humour as a defence mechanism
11:22 Rearranging the furniture
15:14 Playing devil's advocate
19:12 Are you arguing or are you learning?
19:55 Am I attacking you?
20:22 "I'm a very spastic person"
22:35 Knowing when you're triggered
29:49 Still the scared little child
33:47 "I feel like I'm checking out"
34:15 Talking at someone instead of with them
40:25 Defence mechanisms are your talents
42:52 The boss's mom story
44:25 "I don't have boundaries. I have yours."
46:12 Don't send the comedian out every time
48:45 Six foot six, and read as a threat
49:41 The six-foot-six elf
59:22 Forgiveness is a natural flower of understanding

The Kylen and Kenda Show — a mentor and a mentee, arguing their way toward something useful.

It escalates: student debt as indentured servitude, who actually benefits from a broken economy, boomers vs "lazy bones," and whether the doom is real or just your algorithm marketing you an apocalypse. Kenda answers with agency — the MBA she got with no bachelor's, "if you don't ask, they can't say no" — and Kylen keeps naming the darkness until she's in tears. Then he flips the mentorship on its head with the line the whole episode was building to: the only thing you can see in absolute darkness is light.

Chapters:
0:00 Cold open: suit roast + trailer teasers
2:37 The 401k confession
5:04 401k 101: compounding, 59½, penalties
8:16 Credit cards, APR, and the organ-selling riff
10:35 Kylen's counter-philosophy: bet on yourself
12:10 Kenda's priorities lecture: diversify, then decide
16:24 Survival mode: the fridge situation
21:00 Victimhood vs. stomaching the bullshit
24:54 The cost of becoming anything: nursing, debt, $1,000 crutches
28:27 Who benefits from a broken system
32:17 Generational blame: 'their eyeballs work'
35:53 Vitamins vs. the virus: complacency and radical transparency
40:13 The manosphere experiment & chicken-or-egg
43:25 Apocalyptic, or amplified?
46:14 Power, choices, and showing up
50:45 Kenda's tears & the ref is like the weather
55:53 'Be realistic' is a trap
59:47 MBA without a bachelor's: 'watch me'
1:04:41 Personal vs. societal: the Camino gift
1:08:52 'Show me how it affects you' + Mandela's light
1:14:45 Finale: light in absolute darkness

🎙 The Kylen and Kenda Show

Underneath the bit is the real episode. Kylen uses comedy the way some people use a security blanket, and this week he says it out loud: 'I'm like a mix between a golden retriever and a clown' — every charming, loud, look-at-me thing he does traced straight back to a lonely kid who just didn't want to get sent home. We also get the origin story for all of it: the week young Kylen was dead certain his Nintendo was haunted, right up until Dad explained it wasn't a ghost — it was a divorce and an airborne pan of marinara sauce.

Somewhere in there we cross-examine a 10-year-old's 'you suck,' relitigate an apostrophe Kylen swears he'll remember until he dies, argue about whether pain is the only teacher that ever actually works, and debate whether comedy just got too smart for its own good. It's the usual: two people using jokes to sneak up on the truth, then getting caught in the act. Come for the mentor battle, stay for the accidental honesty.

The Kylen and Kenda Show is a mentor and a mentee figuring out ego, insecurity, and connection one conversation at a time. New episode every week.

Chapters:
0:00 Cold open: take your vitamins
3:19 'Do you want me to mentor you?'
3:50 Cross-examining a 10-year-old's 'you suck'
8:10 The bimbo incident (and the case for fear)
14:32 'I remember the apostrophe'
20:07 The haunted Nintendo
25:22 Why pain is the only teacher
40:40 Golden retriever and a clown
42:51 In defense of the Neanderthal
47:19 Has comedy gotten too smart?
54:01 The mentor battle: rock, paper, scissors

🎙 The Kylen and Kenda Show

From there it goes where it always goes on this show. Kylen reframes the phone debate ('what have you designed your phone to be a vector of?'), we make the case for feeling small but not insignificant, and then dating gets serious: Kenda opens up about the emotionally abusive relationship she was in at 19 with a man ten years older — and the deliberate restraint of her therapist mom, who stayed quiet so she could stay close. Kylen owns his side too: the cigarettes, the leather-jacket logic, the bully-baiting — all the same move of trying to prove a value he didn't feel.

We land on the question Kenda asks everyone she loves: do you want to be right, or do you want to get along? Plus a hotboxed Police concert, a bathroom-stall nacho story we apologize for in advance, and Kylen's confession that he can read people perfectly — and has been using it all wrong.

The Kylen and Kenda Show is a mentor and a mentee figuring out ego, insecurity, and connection one conversation at a time. New episode every week.

Chapters:

0:00 — Cold open

1:02 — Back from a week of World Cup crowds

3:35 — Collective effervescence: why crowds feel magical

9:18 — What have you designed your phone to be a vector of?

19:25 — Small but not insignificant

24:52 — Dating, values alignment, and red flags

31:30 — Laughter as the marriage repair tool

42:17 — Why proving your worth pushes people away

49:55 — Where insecurity originates

58:19 — Do you want to be right or get along?

1:01:29 — A confession about reading people

This is the origin episode. Kylen and Kenda lay out the whole reason they're doing this: a phone-addicted, lonely generation that's struggling with technology, late partnerships, hard-to-find jobs, and a quiet inability to connect. Their mission is simple and stubborn — get people back to real community, real dialogue, and the social skills nobody seems to teach anymore. Along the way they get into the near-death tooth story (eight childbirths' worth of pain, apparently), why fighting is wrong but so much fun, and the difference between curiosity and confrontation.

You'll also hear the honest mentor/mentee tension underneath all the jokes. Kenda's line says it all: "I don't have to mentor you... you are not an easy person, and every day I choose it." They dig into red flags versus "the ick," what's actually worth suffering through in a relationship, and why teaching kids real psychology matters before they learn the wrong kind.

So pull up a chair, you little voyeur. New episodes drop here — hit subscribe and come build something better than another night alone with your phone.

Chapters:

0:00 Cold open — "I live in a shed. Peter Pan complex."

1:23 Who Kenda is + her hope: community without phones

4:01 Self-aware but still an infant (road rage, control)

8:42 The fight code & mental toughness

13:54 Kylen almost died from a toothache

20:14 Why "show me the research" really means trust

30:00 Why this generation feels so alone

35:21 Real red flags vs. the "ick"

43:24 Wrap — the origin story

🎙 The Kylen and Kenda Show