This week on the season 2 finale of Cray Dates with Aishah Tries, my childhood friend, Derrick, joins me to share a dating saga that took a turn for the absolutely unhinged. It started with one girl, then somehow led to her best friend, and let’s just say… things got messy fast. But that’s just the beginning. We also dive into the chaos of modern dating—financial expectations, flying people out, and whether any of it is ever really worth it. Buckle up, because this one is a ride.

Follow & connect with @CrayDates across Instagram, TikTok, and YouTube!

This week on Cray Dates, Jeff joins us to share a dating horror story for the books. His date, S.T., was already on edge, and as the night unraveled, things took a truly bizarre turn. Let’s just say, when you take certain items out of the bathroom, people will find another solution… and it won’t be pretty. Tune in for this hilariously absurd tale of bad vibes, bad decisions, and a shocking discovery no one saw coming.

Follow & connect with @CrayDates across Instagram, TikTok, and YouTube!

This week on Cray Dates with Aishah Tries, my older brother Rasheed joins the pod to share a dating story with an unexpected twist—what started as dating a guy selling soap at the mall took a sharp turn when some… extracurricular activities were revealed. We also dive into what should (and shouldn’t) be on your dating profile and the ever-complicated sibling dynamic of having opinions on each other’s love lives. Plenty of laughs, plenty of debates—don’t miss it!

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

This week on Cray Dates with Aishah Tries, Alec joins us to share a story that starts with a blacked-out introduction and only gets wilder from there. He agrees to a date with a woman he has no memory of meeting—no name, no face, nothing. As the night unfolds, she reveals some unexpected truths about her past, and things only spiral from there. Buckle up for a chaotic ride through one of the most unpredictable dates we’ve ever heard.

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

This week on Cray Dates, James joins the pod to share his perspective on why traditional marriage isn’t for him and how he navigates modern dating with that in mind. We also dive into his thoughts on soulmates, deep connections, and what it really means to vibe with someone on another level. A conversation that challenges norms and makes you think—tune in for all the insights and hot takes.

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

This week on Cray Dates with Aishah Tries, Jonathan shares a story about Friendster—a character who stuck around longer than he expected. From dodging confrontation in his 20s to finding himself at dinner with him years later, we explore what happens when you don’t tackle things head on. Plus, Jonathan shares his takes on finding real connections in today’s dating world.

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

This week on Cray Dates, Quincy joins us to share a wild dating story about authenticity—or lack thereof. He opens up about the challenges of navigating relationships in Los Angeles, where appearances and intentions often don’t align. From surprising revelations to insightful reflections, this episode delves into the unique hurdles of dating in a city known for its glitz and complexity. 

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

This week on Cray Dates with Aishah Tries, Kenny shares a story from his early 20s that’s equal parts wild and eye-opening, shaping how he approaches relationships and modern dating. We also dive into his unfiltered thoughts on today’s dating world, the myth of “fairytale” relationships, and the lessons learned from the chaos. Tune in for insights, laughs, and moments that’ll leave you shaking your head. 

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

This week on Cray Dates with Aishah Tries, we’re joined by Michael for an unforgettable story about his whirlwind experience with a woman he met on a dating app, nicknamed Diego. What starts as a promising connection quickly turns into a rollercoaster of surprises and unanswered questions. Tune in to hear how Michael navigates this shocking twist and what he learned along the way.

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.

Welcome to Season 2 of Cray Dates with Aishah Tries! We’re kicking things off with the wild story of the Lying Lawyer—a seemingly good guy whose smooth talk and professional charm couldn’t hide his web of lies. From little fibs to glaring red flags, this episode unpacks how appearances can be deceiving and why trusting your gut is so important in dating. Tune in for the season opener filled with drama, laughs, and lessons learned!

Follow & connect with all things @CrayDates across Instagram, TikTok, and YouTube.