Toby + Chilli's "Crazy First Dates"

Have you ever had a Crazy First Date story that's SO good it needs to be shared with the WORLD?! Remember, doesn’t have to be your worst… just your first!

Episodes

8/9 Crazy First Dates! - Mary Had Some Chance Encounters

August 9, 2022 • 2 min

Mary ran into her ex AND her parents on this first date.

Mark as Played

7/28 Crazy First Dates! - Tenille's Date Had An Interesting Past

July 28, 2022 • 2 min

Should Tenille's date have been more open about his past?

Mark as Played

7/26 Crazy First Dates! - Amanda's Date Had So Many Red Flags

July 26, 2022 • 3 min

Amanda's date checked all of the wrong boxes.

Mark as Played

7/21 Crazy First Dates! - Melissa's Date Had A Weird Way Of Taking Meds

July 21, 2022 • 3 min

Melissa's date really made an impression with the way he took his medication.

Mark as Played

7/19 Crazy First Dates! Sarah from Annandale is late for her first date in stained work clothes!

July 19, 2022 • 3 min

Real stories. Real people. These are your Crazy First Date Stories and this morning, Sarah from Annandale shared her story which found her running late for a first date which she had re-scheduled and so she went after work... in her stained work clothes! Stained with what? You'll have to hear to find out! (7/19/2022)

Mark as Played

7/14 Crazy First Dates! - Marilyn's Reunited With An Old Friend

July 14, 2022 • 2 min

Nothing like a high school reunion on a date.

Mark as Played

7/12 Crazy First Dates! - Klaudia's Date Involved the Afterlife

July 12, 2022 • 3 min

Klaudia's date wanted her to meet an interesting person in his life.

Mark as Played

6/30 Crazy First Dates! - Carrie's Date Took Crazy To New Heights

June 30, 2022 • 3 min

Carrie was surprised with a fear-defying stunt on her first date.

Mark as Played

6/28 Crazy First Dates! - Jenn's Date Had An Interesting Proposal

June 28, 2022 • 3 min

You know what they say, three's a crowd.

Mark as Played

6/23 Crazy First Dates! - Andre's Date Was...Magical

June 23, 2022 • 3 min

Andre's date dabbled in dark magic.

Mark as Played

6/21 Crazy First Dates! - Lori's Date Tried To Save Her

June 21, 2022 • 3 min

Who doesn't love a religious conversion on the first date?

Mark as Played

5/26 Crazy First Dates! - Judy’s Date Is a Sign to Ignore Signs

June 16, 2022 • 2 min

Judy's date should have left her running... But it didn't.

Mark as Played

(6/9) T+C Crazy First Date Stories: Nancy from Baltimore pulled into DRAMA at the TRAILER PARK!

June 10, 2022 • 3 min

Nothing makes a first date memorable like being pulled into some drama - family drama - in a Maryland trailer park! Nancy from Baltimore had quite the time with someone she was set up with...

Mark as Played

5/26 Crazy First Dates! - Iris' date was more than a friend...it was family

May 26, 2022 • 3 min

Iris knew her date too well.

Mark as Played

5/24 Crazy First Dates! - George’s Date Was Purrfect...or Was It?

May 24, 2022 • 3 min

George's date almost killed him but this is a happy story.

Mark as Played

5/19 Crazy First Dates! - Janina's Date Was A Biter

May 19, 2022 • 3 min

Sometimes biting can be sexy but not on this date.

Mark as Played

5/17 Crazy First Dates! - Lisa's Date Pulled A Disappearing Act

May 17, 2022 • 3 min

Lisa's date had an interesting excuse for disappearing for 30 minutes.

Mark as Played

5/10 Crazy First Dates! - Jillian’s Date Proved Six Is a Crowd

May 10, 2022 • 3 min

Two is company...three is a crowd...so what does six people on one date mean?

Mark as Played

5/5 Crazy First Dates! - Carol Had High Expectations For This Date

May 5, 2022 • 2 min

Usually, you don't expect a proposal on the first date.

Mark as Played

5/3 Crazy First Dates! - Kristen's Date Had One Too Many Flaws

May 3, 2022 • 3 min

Kristen's date was a doozy.

Mark as Played

Popular Podcasts

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations.

Crime Junkie

If you can never get enough true crime... Congratulations, you’ve found your people.

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks then look no further. Josh and Chuck have you covered.

The Daily

This is what the news should sound like. The biggest stories of our time, told by the best journalists in the world. Hosted by Michael Barbaro. Twenty minutes a day, five days a week, ready by 6 a.m.

The Bobby Bones Show

Listen to 'The Bobby Bones Show' by downloading the daily full replay.

Advertise With Us

Toby + Chilli's "Crazy First Dates"

Episodes

.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}8/9 Crazy First Dates! - Mary Had Some Chance Encounters

.css-r6mb8g{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:1;overflow:hidden;}7/28 Crazy First Dates! - Tenille's Date Had An Interesting Past

7/26 Crazy First Dates! - Amanda's Date Had So Many Red Flags

7/21 Crazy First Dates! - Melissa's Date Had A Weird Way Of Taking Meds

7/19 Crazy First Dates! Sarah from Annandale is late for her first date in stained work clothes!

7/14 Crazy First Dates! - Marilyn's Reunited With An Old Friend

7/12 Crazy First Dates! - Klaudia's Date Involved the Afterlife

6/30 Crazy First Dates! - Carrie's Date Took Crazy To New Heights

6/28 Crazy First Dates! - Jenn's Date Had An Interesting Proposal

6/23 Crazy First Dates! - Andre's Date Was...Magical

6/21 Crazy First Dates! - Lori's Date Tried To Save Her

5/26 Crazy First Dates! - Judy’s Date Is a Sign to Ignore Signs

(6/9) T+C Crazy First Date Stories: Nancy from Baltimore pulled into DRAMA at the TRAILER PARK!

5/26 Crazy First Dates! - Iris' date was more than a friend...it was family

5/24 Crazy First Dates! - George’s Date Was Purrfect...or Was It?

5/19 Crazy First Dates! - Janina's Date Was A Biter

5/17 Crazy First Dates! - Lisa's Date Pulled A Disappearing Act

5/10 Crazy First Dates! - Jillian’s Date Proved Six Is a Crowd

5/5 Crazy First Dates! - Carol Had High Expectations For This Date

5/3 Crazy First Dates! - Kristen's Date Had One Too Many Flaws

Popular Podcasts

For You.css-1r2bfgw{margin:0 0 -2px 5px;}

8/9 Crazy First Dates! - Mary Had Some Chance Encounters

7/28 Crazy First Dates! - Tenille's Date Had An Interesting Past

For You