Sep 17, 2026 · 2 hr 7 min · 17 segments
In this episode Rachel is joined by her friend Shiffy! Shiffy tells Rachel all of her craziest dating stories, and some of them seem like they could have ended a lot worse than they did. Shiffy knew…
Yeah it's also I was talking to my friend about this and I feel like I've said it on the podcast before you can know someone but you don't know them in a dating context unless you've dated them.
yeah yeah that is so true
like even like my friends i was talking to a guy friend about this and i don't remember how it came up oh maybe he was like saying something about wanting to date one of my friends and i was like okay but like don't do anything that like she's not gonna be my friend anymore
yeah and
he's like oh you have so little faith in me and i was like I don't know how you are as a dater.
Yeah.
I'm from a different perspective.
Yeah.
I'm like, I know you as a friend.
I don't know you as a dater.
I don't know what you do on dates because people pull this crazy BS.
Yeah.
And yeah.
Also like what I don't understand is if you can't pay the bill, you don't have to go somewhere that expensive.
You also don't have to order everything on the menu.
Exactly.
And it actually makes me uncomfortable because, going well shitty situation nation knows i've said this before i don't love going out to dinner on a first date um i'm like okay with it depending on the place but i get uncomfortable with the idea of somebody spending so much money on me because again i'm with you i'm
yeah
i'm not paying
especially right away what are they trying to
yeah and like
It's nice, I guess, if it happens and he's a great guy and that's just his style of whining and dining you, but...
Yeah, for sure.
And at the end of the day, like, I am an adult and I'm tired and...
If we're going out on a weeknight after work, like, I want dinner.
Yeah it's also I was talking to my friend about this and I feel like I've said it on the podcast before you can know someone but you don't know them in a dating context unless you've dated them.
yeah yeah that is so true
like even like my friends i was talking to a guy friend about this and i don't remember how it came up oh maybe he was like saying something about wanting to date one of my friends and i was like okay but like don't do anything that like she's not gonna be my friend anymore
yeah and
he's like oh you have so little faith in me and i was like I don't know how you are as a dater.
Yeah.
I'm from a different perspective.
Yeah.
I'm like, I know you as a friend.
I don't know you as a dater.
I don't know what you do on dates because people pull this crazy BS.
Yeah.
And yeah.
Also like what I don't understand is if you can't pay the bill, you don't have to go somewhere that expensive.
You also don't have to order everything on the menu.
Exactly.
And it actually makes me uncomfortable because, going well shitty situation nation knows i've said this before i don't love going out to dinner on a first date um i'm like okay with it depending on the place but i get uncomfortable with the idea of somebody spending so much money on me because again i'm with you i'm
yeah
i'm not paying
especially right away what are they trying to
yeah and like
It's nice, I guess, if it happens and he's a great guy and that's just his style of whining and dining you, but...
Yeah, for sure.
And at the end of the day, like, I am an adult and I'm tired and...
If we're going out on a weeknight after work, like, I want dinner.
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