Toby + Chilli's "Crazy First Dates"

Wendy's date shared a little too much about his past life.See omnystudio.com/listener for privacy information.

Andrew's date was really opposed to him paying! You have to listen to hear what she did!See omnystudio.com/listener for privacy information.

Emily's date had a weird request for the repayment of $11.See omnystudio.com/listener for privacy information.

Stacey's date had an interesting past and proposal.See omnystudio.com/listener for privacy information.

Barbara's date took 6 months! You have to hear this.See omnystudio.com/listener for privacy information.

Ally's date involved going to jail...but it is not what you think!See omnystudio.com/listener for privacy information.

Was Andrew stood up on his date? You have to listen to find out!See omnystudio.com/listener for privacy information.

Jennifer made quite an impression on this date.See omnystudio.com/listener for privacy information.

Tiffany's date was over in MINUTES. You have to hear why!See omnystudio.com/listener for privacy information.

Paola's date seemed like Prince Charming until the end.See omnystudio.com/listener for privacy information.

Corbin's date was more into his dad than him #OUCHSee omnystudio.com/listener for privacy information.

Tahlia's date turned into a business meeting!See omnystudio.com/listener for privacy information.

Lynn's date took an emotional turn.See omnystudio.com/listener for privacy information.

Bethany's date was one disaster after another between co-workers but the ending will surprise you.See omnystudio.com/listener for privacy information.

Mandi's date is probably the messiest date we've heard in a while.See omnystudio.com/listener for privacy information.

Jason's date was with lady luck in Las Vegas!See omnystudio.com/listener for privacy information.

Keri had to sneak out of her date because it was THAT bad!See omnystudio.com/listener for privacy information.

Lynne's date was more of an interrogation than a date.See omnystudio.com/listener for privacy information.

Mary had an out of this world date...literally.See omnystudio.com/listener for privacy information.

Nancy really toughed it out during her date but at what cost.See omnystudio.com/listener for privacy information.

Ed's date had a weird fashion emergency.See omnystudio.com/listener for privacy information.

The classic dine and ditch for Cheryl!See omnystudio.com/listener for privacy information.

Nothing like meeting the entire family on the date.See omnystudio.com/listener for privacy information.

Kate's date really got a 2 for 1 special on her date.See omnystudio.com/listener for privacy information.

Kevin's life was threatened TWICE during his date.See omnystudio.com/listener for privacy information.

Three is a crowd even if the third party doesn't talk.See omnystudio.com/listener for privacy information.

Emily's date had very interesting hobbies.See omnystudio.com/listener for privacy information.

Kerri's date got caught in a hairy situation...See omnystudio.com/listener for privacy information.

Sharon beach date left her stuck in the sand.See omnystudio.com/listener for privacy information.

Megan took a risk and decided to surprise her date in New York!See omnystudio.com/listener for privacy information.

Eve's date started with a rugby match and ended in love!See omnystudio.com/listener for privacy information.

Gina and her date had an unwanted visitor!See omnystudio.com/listener for privacy information.

Robin may have had the fastest date ever.See omnystudio.com/listener for privacy information.

Jay's date used her to get to another woman. You have to hear this.See omnystudio.com/listener for privacy information.

Tina has a surprise third wheel on her date.See omnystudio.com/listener for privacy information.

Kianna's date is the classic case of mistaken identity!See omnystudio.com/listener for privacy information.

John's date when overboard...literally.See omnystudio.com/listener for privacy information.

Diane's date ended up in the land of the unknown. You have to hear how her date ended.See omnystudio.com/listener for privacy information.

Laura's date really wanted to look good for her during the date.See omnystudio.com/listener for privacy information.

Michele would her date two thumbs down...or maybe one thumbSee omnystudio.com/listener for privacy information.

Andrew's date took a bite out of love...literally.See omnystudio.com/listener for privacy information.

Two dates. Two Weeks. And one weird overlap.See omnystudio.com/listener for privacy information.

This date was all over Maryland and it has a crazy twist ending!See omnystudio.com/listener for privacy information.

It is never a good sign when you have to snoop after a date.See omnystudio.com/listener for privacy information.

Jena's date involved a dirt bike and an infection. Wow.See omnystudio.com/listener for privacy information.

Kim definitely got her 10,000 steps in on this date!See omnystudio.com/listener for privacy information.

This date was one disaster after another!See omnystudio.com/listener for privacy information.

Three is really a crowd on a date!See omnystudio.com/listener for privacy information.

What do you do when your date gets deployed before your first date?See omnystudio.com/listener for privacy information.

Mehdi was over two hours late to his date and he tried to serenade his way out of it. But did it work?See omnystudio.com/listener for privacy information.