Tuesday, October 7, 2025: Anna’s Haunted House; Raven’s New Diet; What Your Dog Ate!

Tuesday, October 7, 2025: Anna’s Haunted House; Raven’s New Diet; What Your Dog Ate!

Experts say waiting is good for your health and can be fun! Anna and Raven talk about the longest times they had to wait!

It’s National Taco Day and Taco Bell has $1 tacos! Anna and Raven talk to Chef Plum on how you can make them at home for just as cheap! He has the secret to recreate them! Find Chef Plum on his podcast Plum Luv Foods everywhere!

Anna never thought her house was haunted until the other night! She has the proof! Go on our Instagram @AnnaAndRaven to see for yourself!

Raven has made some improvements with his diet and his wife wants to send him to the office with plant-based butter! But she wants to put his name on it!

Anna went out with her girlfriends the other night! She was so hungry and made a revelation about going out to eat with her friends! Does everyone go through this or is it just a woman thing?

Anna’s six-year-old was going to bring her first MLB baseball but their dog ate it! What did your dog eat?

Heather is a class mom, and she was last year too. There is one student that is in her son’s class (again) that didn’t pay any of the dues or contribute to any of the teacher collections last year. She sent many emails and tried to call his parents to no avail. Ultimately, she paid for the child’s portion. She is so annoyed that parents could be so unresponsive that she wants to send them a certified letter explaining that she paid for their son last year and that she expects them to contribute this year. Her husband, Steve, says that even though it’s a private school, this should have been an admin issue. No one told her to cover the costs for the child, she took it upon herself to do that, and this is overstepping her role as a class mom.

Jennifer, Anna, and Lauren a chance to win $600! All they have to do is answer more pop culture questions than Raven in Can’t Beat Raven!

SchmoozaPalooza 2.5

SchmoozaPalooza 2.5

Join us for SchmoozaPalooza 2.5 brought to you in partnership by the Greater Valley Chamber of Commerce, the Bridgeport Regional Business Council, and the Monroe Chamber of Commerce Wednesday, October 29, 2025 2:00 PM – 5:00 PM at the Trumbull Marriott Shelton, 180 Hawley Lane in Trumbull.


More info and Registration

SchmoozaPalooza is back with lots of opportunities to network! It is all about business in action and making connections.

This premier tabletop tradeshow highlights some of the best from the Greater Bridgeport, Monroe, and Valley region. Local businesses across every industry showcasing their must-have products and services. And, for an added treat, attendees can indulge in Eats & Treats all around the exhibit hall – highlighting some of our region’s culinary gems.

Monday, October 6, 2025: Where Are the Gold Diggers; Sexiest Man Alive; Trying Taylor Swift’s Posture Bra!

Monday, October 6, 2025: Where Are the Gold Diggers; Sexiest Man Alive; Trying Taylor Swift’s Posture Bra!

The job market is so over saturated, and some employers are charging applicants to apply for work! Would you pay to apply for The Anna and Raven Show?

Are you up to date on this week’s biggest news story? Anna and Raven will get you caught up on the trending news including Sean Combs conviction and the Full Harvest Moon!

What’s trending for costumes this Halloween? Anna and Raven speak to the Marketing Director of The Halloween & Costume Association, Whitney Hatfield! She previews what people will be wearing this Halloween, you can find here at https://www.hiaonline.org/.

A company looked into which states have the greatest number of Gold Diggers! There are three Gold Digger characteristics to look for before going on a date! Anna’s husband is a food digger!

You can now vote for the People’s Magazine Sexiest Man Alive! Anna and Raven go through the list and then vote on what the sexiest characteristics are!

Are you up to date on this week’s biggest news story? Anna and Raven will get you caught up on the trending news including Instagram’s 15th birthday and adult field days are taking over the country!

Taylor Swift wears a sports bra that corrects your posture, so Anna wanted to try it! Find out if it works!

Lainey Wilson stopped a show to hug and thank a fan that had been there “from the beginning.” Anna and Raven talk about what they were a DAY ONE fan of, long before it was popular?

Taylor is two years into her new job and has gotten an offer to move to Silicone Valley to pursue her dream job in the technology industry. Her husband, Randy, feels that they are better suited where they are because all of their family is there and both of their current jobs have them in a great financial position in life.  She argues that this is her dream, and they should explore it while they still don’t have kids, he says that it’ll just make life more difficult if they have kids and aren’t close to their parents. What do you think?

Mary and Ed have a chance to win $500! All they have to do is answer more pop culture questions than Raven in Can’t Beat Raven!

Trending Halloween Costume Preview!

Trending Halloween Costume Preview!

What’s trending for costumes this Halloween? Anna and Raven speak to the Marketing Director of The Halloween & Costume Association, Whitney Hatfield! She previews what people will be wearing this Halloween, you can find here at https://www.hiaonline.org/
Photo Credit: The Halloween & Costume Association

Win tickets to the Haunted Hayride at Legends of Fear

Win tickets to the Haunted Hayride at Legends of Fear

Listen to Kevin Begley all this week on STAR 99.9 at 4pm to play “I Should Have Known That” for your chance to win a four pack of tickets on the Haunted Hayride at Legends of Fear at Fairview Tree Farm in Shelton!

Contest Line: 800-330-9999

Experience one of the most unique haunted traditions in New England.

Board one of their tractor pulled hay wagons into thier fields and forest of fear for thirty minutes of spine chilling fun. You may try and huddle together for safety, but in their domain they live to hear you scream! Into the darkness you will descend imprisoned on their sinister ride… deeper and darker the driver will go. No one will hear your curdling screams over the chainsaws and the clowns’ maniacal laughter. There is no escaping the nightmares they create.

Buy Tickets Now

Annual Domestic Violence Awareness Month Vigil

Annual Domestic Violence Awareness Month Vigil

The Center for Family Justice (CFJ) will host its annual Domestic Violence Awareness Month Vigil from 5:30 until 7:30 p.m. on Wed., Oct. 15 at the Hartford HealthCare Amphitheater in Bridgeport. Chief Rod Porter of the Bridgeport Police Department will join CFJ President & CEO Deb Greenwood as co-emcee.

This year’s vigil will honor the lives tragically lost to domestic violence homicide over the past year, while also recognizing those in our community who stand as dedicated supporters of CFJ’s mission.

We hope you can join us for a night of remembrance, solidarity, and action as we work together to provide life-saving programs and services to victims of domestic violence.

The event is free and open to the public.

The Center for Family Justice provides free and confidential programs and services for those impacted by domestic violence, sexual violence and child abuse. We serve Bridgeport, Easton, Fairfield, Monroe, Stratford and Trumbull.

Join Kevin at the Bridgeport Islanders Home Opener!

Join Kevin at the Bridgeport Islanders Home Opener!

Join Kevin Begley before the Bridgeport Islanders Home Opener at Total Mortgage Arena from 4-6pm Saturday October 11th!

Stop by the Star 99.9 Tent on your way into the game!

Gameday Details 

Providence Bruins | Saturday, October 11th | 7 PM 

Giveaway Details 

Foam Claw – First 2,500 fans

Promotional Night Details 

  • First Sound Tigers Saturday!
  • Pregame Fan Fest between 4:00 p.m. and 6:00 p.m. in the plaza featuring live music, 25th Anniversary retail items, activities, and more!

Get your tickets now!

Can You Eat It?

Can You Eat It?

If you have to look up if you can eat these, it’s safer to put it down! Yes, that includes Puff Ball Mushrooms from your neighbor’s lawn!

https://studio.youtube.com/video/OxLceGcedgs/edit
Friday, October 3, 2025: ‘The Life of a Showgirl’; Brad or Rant About Taylor Swift; Mommy Margarita!

Friday, October 3, 2025: ‘The Life of a Showgirl’; Brad or Rant About Taylor Swift; Mommy Margarita!

What would you do if you walked into work and you were asked to remove your shoes before entering? That’s the reality for people in the UK! Anna thinks it might make people more creative!

Are you up to date on this week’s biggest news story? Anna and Raven will get you caught up on the trending news including Taylor Swift’s new album ‘The Life of a Showgirl’!

The Anna and Raven Roadshow is back! Expert appraiser, Ryan Brechlin from Good Bottle Auctions will be appraising items from Lynn! Some of these items are worth way more than what you thought!

Anna and Raven speak to Swiftie, Brooke Fitzsimmons, about the new Taylor Swift album and get her thoughts on it!

Anna and Raven open the floor for you to brag or rant about Taylor Swift! If you like her, they will play another Taylor Swift song, if you don’t like her music, you can request a different song!

Every week Anna and Raven invite a middle school student to participate in Middle Schooler News! They report the headline news and Anna and Raven comment on it! This week Silas joins the show and Anna and Raven find out what’s going on in the world!

Anna says for all you do, and all you put up with this week, you’ve earned yourself a drink. What did you do to earn your Mommy Margarita?

Rick’s girlfriend, Jessica, does not like the fact that he liked a picture of an ex-girlfriend on social media. Rick feels that there is no issue with this because they have been friends for a long time and have both expressed that they both would never get back together, they’re better off as friends. Jessica claims that it does not matter and the only female that he should be liking pictures from is her, it’s rude and makes people talk. Whose side are you on?

Carolina and Cathy have a chance to win $400! All she has to do is answer more pop culture questions than Raven in Can’t Beat Raven!