Dating And Other Fucked Up Stories
Upon my debut into the modern dating world, I thought everyone had the same concept of what normal, decent, and acceptable was. It took the first unsolicited dick pic to bitch slap me into reality. And Holy Shit! From that point on I knew it was time to buckle up, ladies & gentlemen. Because I was in the motha’ f*ckin’ Wild Wild West! This podcast chronicles the horrifying, yet hilarious dating adventures of Rachel Ash. None of the details in these stories have been altered.
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Episodes
82 episodes
S3 Ep 76: Hitting on Married Women
August 2026. For most women, noticing a wedding ring ends the inquiry. Certain men treat it differently. The ring does not close the door; it merely changes the sales strategy...
S3 Ep 75: Pretend Boyfriend
August 2026. I had a pretend boyfriend for a day. No, seriously. It's a modern-day Cinderella story. The clock strikes midnight, and suddenly your temporary relationship spell is broken. It's basically a free trial. No monthly subscription. No ...
S3 Ep 74: The Fantasy, The Fun, & The F*ckery
July 2026. When a 45-year-old man dates a 27-year-old woman, society is basically like, “Congratulations, Brad.” But when a woman dates younger, suddenly everyone becomes a developmental psychologist.
S3 Ep 73: The Love Loop
July 2026. Your greatest strength in life can become a liability in love. Late one night while doom scrolling, I have a life-changing epiphany.
S3 Ep 72: Women Grow Men Up
Do women really grow men up? I share some of my first-hand experiences of growing up the men I have been in relationships with. From my ex-husband to as recent as The Actor.
S3 Ep 71: You Can't Have Your Cake and Eat Me, Too
July 2026. Sitting at my favorite coffee shop in Fort Lauderdale when suddenly I am approached by a hungry New Yorker looking for some extra cake.
S3 Ep 70: The Cost of Dating
The average cocktail costs $25. What else is that date costing you?
S3 Ep 69: The D-Tox
June 2026. Sometimes you need to take a break from the "D" and get some R&R. When dating begins to feel dismal, it's time to hit RESET and go back to you.
S3 Ep 68: Delete the Apps Movement
June 2026. Dating Apps have become a thing of the past. IRL experiences have taken over. But where and how do we meet people?
S3 Ep 67: Dating Potential
May 2026. Part II of the Mr. Boston dating adventures. I quickly learn that Mr. Boston has a BIG secret. Maybe too big...
S3 Ep 66: The Bumble Fumble
April 2026. Mr. Boston cancels our date suddenly and leaves me on 'delivered' all night...
S3 Ep 65: Why do Men Come Back?
We dive into the 5 Reasons Why Men Come Back and what to look for when they do come back.
S3 Ep 64: He Came Back
May 2026. The Actor makes an encore performance back into my life. All this after 5 months no contact.
S3 Ep 63: Man with Three Cats
May 2020. This is the story about the cat man who loved Shia LeBuff and bike rides by the beach. It was the pandemic, what can I say?
S3 Ep 62: Types of Men on Dating Apps
We dive into the different types of men & women you find on dating apps. It's all the red and green flags in one place so you don't get stuck in confusion.
S3 Ep 61: Tinder Games
September 2020. The height of the pandemic. I sit across from a very scared lawyer who tells me about a secret game he used to play...
S3 Ep 60: I Saw a Ghost
March 2026. I come face-to-face with a real life ghost. My face turns white, my stomach drops, and horror ensues...
S3 Ep 59: He's Married!
Summer 2025. He was 52 going on 39 - in his own delusional mind. It had been awhile since I had caught a catfish. I was overdue.
S3 Ep 58: Dating Younger Men - Part III
The Actor invites me to visit him in NYC. Leading up to the trip he promises to spoil me the whole weekend. Once I arrive he asks me to pay for his drinks...and I'm left wondering who's spoiling who.
S3 Ep 57: Dating Younger Men - Part II
Part II. November 2025. The Actor puts on a show. I realize I am the audience, and he is the star in a production of his own cruel intentions.
S3 Premiere - Ep 56: Dating Younger Men
Season III Premiere. October 2025. Decided to ditch Millennials and date younger - 13 years younger to be precise. Had I been dating the wrong generation the whole time?
S2 Finale: The Peacock - Part II
Season 2 Finale. The Peacock's ex-girlfriend tells me her side of the story. After hearing her shocking account, I start to wonder who is telling the truth.
S2 Ep 54: The Peacock
November 2024. What's the harm in mixing business with pleasure? This story is not about a turkey, but it is about another kind of bird... A peacock crosses my path. As time goes by, I begin to pluck the feathers one-by-one to reveal who this m...