Armchair Expert with Dax Shepard
Armchair Expert with Dax Shepard

Armchair Anonymous: Bad Dates II

April 10, 2026 • 55m

Summary

⏱️ 6 min read

Overview

A hilarious collection of dating disasters from Armchair Anonymous, featuring stories of boundary lists, bizarre behavior, and unexpected twists. From a first date with an aerospace engineer who confessed love in 'all Greek meanings' to a wife's unforgettable story of her husband's spicy wing catastrophe that led to a McDonald's milkshake remedy, these tales prove that sometimes the worst dates make the best stories—and occasionally lead to marriage.

The Christian Date with a Comprehensive List

Bailey from Grand Rapids shares her 2019 first date with a Notre Dame aerospace engineering student she met on Tinder. What started as a seemingly normal date at Cheddar's took an unexpected turn when her date arrived in a full suit and pulled out a written list of physical boundaries including 'no touching, no caressing, no fondling, no squeezing, no stroking.' The evening concluded with him declaring love in all Greek meanings and suggesting a walk in the woods—all on a first date.

  • Met on Tinder and FaceTimed for weeks before meeting in person at Cheddar's restaurant
  • Date arrived in a full suit and tie while Bailey wore jeans and a nice top
  • He pulled out a written list from his pocket detailing physical boundaries: no touching, caressing, fondling, squeezing, or stroking
  • Had a photo of Bailey from Facebook (not sent by her) saved on his phone
  • After the movie, he declared he loved her 'in all of the Greek meanings of love' and asked if she loved him back
  • He suggested a walk in the forest behind the parking lot after professing his love
  • Bailey is now married to a 'golden retriever husband' she met on Hinge
" I want to talk about my physical boundaries with you. "
" There's no way that that would happen now. I think if it happened now, it would be totally different. "
" I love you in all of the Greek meanings of love. "

The Austin Trail Date Gone Wrong

Grace recounts a terrifying 2018 first date in Austin that began at a bar and escalated into a nightmare. Her date drove her to what he claimed was a scenic overlook in Zilker Park, brought out a giant backpack with champagne and a professional camera, then stole her phone to go on a solo night hike. The situation deteriorated when he forced his way into her apartment and passed out on her couch, yet texted the next day suggesting another date.

  • Met on Bumble after just three weeks of living in Austin, first person she matched with
  • Date suggested visiting a lookout spot after drinks, drove 20+ minutes to a residential area and trailhead at 9 PM
  • He pulled out a giant backpack containing champagne and a professional camera at the clearing
  • Grabbed her phone claiming his flashlight was broken and disappeared on a solo night hike
  • After returning, he insisted on walking her to the door as 'a gentleman' then forced his way into her apartment
  • He passed out on her couch while she locked herself in her bedroom all night
  • Texted the next day saying he had an awesome time and wanted to hang out again
" You're so lame. You're so boring. "
" He grabs my phone out of my hand. And he says, the flashlight on my phone is broken. I need to take yours to go on my hike. "
" I was so embarrassed that I let it get to this point that I didn't want to call anyone. "

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