Armchair Expert: Armchair Anonymous — Bad Dates II
April 10, 2026
Host: Dax Shepard
Co-host: Monica Padman
Theme: Listeners call in to share their worst date experiences, which run the gamut from hilarious and awkward to genuinely unsettling.
Episode Overview
In this episode, Dax Shepard and Monica Padman invite listeners to share stories of their most disastrous dates. The hosts react in real-time, offering commentary, support, and plenty of laughs. The stories highlight the unpredictable, uncomfortable, and occasionally bizarre realities of modern dating—showcasing both the vulnerability and sheer messiness of being human.
Featured Stories & Key Segments
1. Bailey: The List of Boundaries
[04:01–17:41]
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Background: Bailey, a Michigan elementary school teacher, recounts her most memorable bad date from 2019.
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Setup:
- Met Evan, an aerospace engineering student at Notre Dame, through Tinder.
- Emphasizes her approach: safety precautions, sharing location with friends.
- First meetup at Cheddar’s, a “Midwest fancy” restaurant.
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Memorable Moments & Quotes:
- Suit at Cheddar’s:
Bailey: “He’s wearing a full suit, tie and everything.” [08:00]
Dax: “Oh, wow. Were you in a ball gown?” [08:02] - Physical Boundaries Contract:
Evan presents a handwritten list with “no touching, no caressing, no fondling, no squeezing, no stroking.” [08:41]
Monica: “Oh my God.” [08:52]
Dax: “This list is somehow more perverse than just a note that said, ‘I love hand stuff.’” [08:53] - Phone Screensaver Shock:
Evan’s phone background is a photo of Bailey, one she never sent him, indicating he’d “gone searching for it.” [11:16] - Love Bombing:
After a silent movie night, Evan says: “I love you. In all of the Greek meanings of love in the Bible…” [12:50]
Dax: “In the panoply of Greek terms.” [12:52] - Uncomfortable Escape:
After declining a walk with him at night, she feigns a call from her mom and flees. [14:07]
- Suit at Cheddar’s:
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Reflection:
- Hosts consider whether some of his behavior reflects neurodivergence.
- Bailey now views the experience with more compassion but remains very unsettled by the overt displays of attachment and boundary “contract.”
- Bailey gives a shout-out to her coworkers and commends the open-mindedness of the show. [16:20–17:38]
2. Grace: Lost in Zilker Park
[22:13–31:18]
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Background: Grace, recently relocated to Seattle, shares a bad date story from her time in Austin in 2018.
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Setup:
- Met the man on Bumble. First date: started normally at a bar in Austin.
- He offers to show her a “hidden” skyline view; she agrees, despite cautious instincts.
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Events:
- Unexpected Detour and Red Flags:
He drives her 20–30 minutes out of the way, then pulls out a large backpack in a remote park at 9 p.m.
Concern sets in: “Maybe I shouldn’t go to a second location on a first date.” [24:34] - Bizarre Outing:
Unzips a backpack to reveal champagne and a professional camera—proceeds to take photos (not of her).
Champagne Chugging & Stone-Cold Columns:
He climbs stone columns, invites her up, calls her “boring” and “lame” when she declines and begins yelling. [26:07] - Escalation to Danger:
- He grabs her phone for flashlight purposes and leaves her alone in the dark.
- Local teens ignore her pleas for help.
- Upon his return, he wants to go out drinking.
- Grace gives her real address so he’ll drive her home, trying to appease him.
- At her apartment, he insists on being a “gentleman,” forces a goodnight kiss, follows her inside, and refuses to leave, passing out on her couch.
- She barricades herself in her bedroom until he leaves. [29:09]
- Aftermath:
He texts the next day: “I had an awesome time, let’s hang out again.” [29:37]- She blocks him—no reply.
- Unexpected Detour and Red Flags:
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Memorable Commentary:
- Monica: “This is horrible.” [27:33]
- Dax: “I’m glad you made it out of Zilker Park alive.” [31:03]
- Reflect on dating app accountability, the difficulty of reporting, and the mix of shame and survival instincts.
3. Tabitha: The Spicy Wing (and Milkshake) Catastrophe
[33:02–46:40]
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Background: Tabitha, originally from Southern California but living in Louisville, Kentucky, tells a story that is both mortifying and hilarious.
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Setup:
- Dating Andrew for a couple months; this is her “meet the family” moment during a Man vs. Food-inspired spicy wing challenge at a restaurant.
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Events:
- The Wing Challenge:
Andrew, his father, and brother attempt the restaurant’s insanely spicy wings, wearing gloves and needing to sign a waiver. - Immediate Regret:
The men flee to the alleyway, vomiting violently. [39:12] - A Horrific Turn:
Andrew helps clean up, then uses the restroom without washing hands first—resulting in hot sauce on his penis. [40:47] Andrew (panicking): “There’s hot sauce on my dick!” [40:47] Tabitha: “I’m trying to splash the milk in the alley.” [41:16] - Things Escalate:
- Father, brother, and Andrew all in varying states of distress.
- Andrew requests his mom buy him a milkshake to—literally—put his penis in it, in a McDonald’s parking lot. [43:04]
- The family drives home in silence, Andrew sitting in the backseat with his genitals immersed in the milkshake.
- The Wing Challenge:
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Memorable Quotes:
- Tabitha: “His mom and dad are...‘don’t sleep in the same room until you’re married’ nice, not wiener out in an alley nice.” [41:40]
- Monica: “It seems like he just liked what the milk felt like. And he’s like, I want more of that.” [44:18]
- On their relationship: “Not only was it a bad date, but it also doubled as the first time I met my in-laws.” [44:34]
- Yes, Tabitha actually married Andrew: “He does not have a dairy kink, can confirm.” [44:36]
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Host Reflection:
- Milk as a remedy for hot sauce is debated.
- Dax: “Milk in the same way they give you water. But it doesn’t neutralize capsaicin…It can’t reverse what happened.” [45:15]
4. Sam: The Bag on the Foot and a Bizarre Restaurant Experience
[47:25–61:19]
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Background: Sam, from Topanga (originally UK), reflects on a date he claims he blocked from memory—a decision vindicated by retelling it.
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Setup:
- 2009, Thousand Oaks/Simi Valley, meets a Danish woman online.
- He picks her up, immediately notices she’s aged beyond profile photos and is wearing a grocery store bag tied over her foot.
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Events:
- Odd Details Pile Up:
- Blames “injury” for bag but is evasive.
- Stops at a pet store: She chain-smokes inside, shops for pet supplies with no actual dog, drags the bagged foot like a zombie.
- At a restaurant, repeatedly calls the server “bitch” – it escalates from playful to disruptive. [54:03]
- Drinks heavily, demands more wine, volume increases.
- On the return drive, she begins screaming: “Where are you taking me? You’re going to murder me! You’re going to rape me!” [56:58]
- Resolution:
- Arrives at her home; her husband greets him, explains: “Don’t worry, she does this all the time. She’s not taking her meds.” [58:16]
- Sam flees in shock.
- Host Analysis:
- Dax: “It sounds a very bipolar episode.” [58:16]
- Monica: “Maybe the husband is the most patient person on earth, clearly.” [58:40]
- Sam’s Reflection:
- He went on to meet his now-wife online; hosts note his luck swings between extremes.
- Odd Details Pile Up:
Notable Quotes & Reflections
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On Modern Dating:
- Monica: “There are a lot more bad dates than good ones.” [00:13]
- Dax: “Everything happens in this. Please enjoy Bad Dates part two.” [00:56]
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On the boundary-list:
- Dax: “This list is somehow more perverse than just a note that said, ‘I love hand stuff.’” [08:53]
- Monica: “He’s thought through all the things. Squeezing, stroking.” [09:00]
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On App Accountability:
- Dax: “You should be able to [review people on dating apps], but so many people are scorned…everyone would be bagging on each other who didn’t get picked.” [30:33]
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On suffering through a date:
- Dax: “I have had the experience...where I had met someone on MySpace and then when I met him in real life, it was dramatically different...I felt guilty and I proceeded.” [61:46]
Timestamps for Key Segments
- [04:01] — Bailey’s story begins
- [08:41] — The boundaries contract emerges
- [12:50] — “I love you” in all Greek biblical meanings
- [14:07] — “Do you want to go on a walk?”/her escape
- [22:13] — Grace’s Austin date nightmare starts
- [25:12] — The backpack champagne/sketchy hike reveal
- [29:09] — Grace hides in her room; date passes out
- [33:02] — Tabitha’s spicy wing challenge date
- [40:47] — “There’s hot sauce on my dick!”
- [43:04] — Milkshake in McDonald’s parking lot
- [47:25] — Sam joins; bag-on-foot story begins
- [54:03] — Bizarre restaurant ‘bitch’ exchanges
- [56:58] — Public hysterics, culminating in home drop-off
- [58:16] — Husband explains her mental health
- [61:46] — Host reflection on guilt/dating
Tone & Style
- Conversational, humorous, and empathetic—never mean-spirited, even with the wildest stories.
- Dax and Monica bring warmth, curiosity, and self-deprecation, still centering the guests’ voices.
- Regular tangent into dating philosophy, pop culture references, and a running debate on milk’s medicinal powers.
Listener Shout-Outs
- Bailey: Shout out to her coworkers for covering her class so she could record. [16:20]
- Grace: Shout out to her sister Lara, fellow Armcherry. [31:22]
Episode Takeaways
- Modern dating is a minefield—sometimes traumatic, often weird, and occasionally hilarious in hindsight.
- Vulnerability and open conversation make even bleak stories feel communal and empowering.
- For all the bad dates shared, several callers end up in happy marriages, proving that perseverance sometimes pays off.
- There’s no shortage of “bad date” material for Dax and Monica’s (and listeners’) amusement.
“Your experience on Planet Earth is just as valid as mine. I’m just having one. You’re having one. I’m curious about yours.” — Dax Shepard [17:27]
End of Summary