Episodes 23
Avg. Duration 55m
Activity Dormant
Since Feb 2024
Latest Episode Feb 2025

Publishing Details

Schedule
Weekly
Format
Episodic
Hosting
anchor.fm

Contact & Outreach

About This Podcast

Welcome friends to Awkward Affairs. I'm Cindy, I've been in the dating game for 20 years. It sounds crazy to say that out loud. Within those 20 years I've been divorced once, engaged two more times, my heart has been broken twice…spoiler alert, my broken hearts were not the people I was engaged to and there has been so, so, so, many stories of awkward affairs, casual encounters, and all the emotional highs and lows that come with it. I'm here to share stories, laugh, cry and continue to navigate this insane journey that has been dating and living in a digital era.

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Recent Episodes

S2E2 Love, Hayli

Feb 21, 2025 1h 51m

Welcome Friends!Hayli is my special guest on this episode of Awkward Affairs. Hayli and I have known each other for 15 years. She's a beautiful example of designing the life you desire. Please join…

S2E1 Welcome Back!

Feb 14, 2025 52m

Welcome back! How exciting to present to you all season two episode one of Awkward Affairs! Today I will be discussing what I’ve been up to for the last several months give you an update on my dating…

S1E20 WWCD What Would Cindy Do?

Jul 10, 2024 1h 1m

Hi Friends! Welcome to the 20th episode and a fun conversation with fan favorite Lili! Today she asks me what I would do in certain relationship or dating situations. Please join me for some good…

College Crushes pt. 2

Jul 03, 2024 29m

Welcome Friends! Jessica and Donna are joining me for part 2 today to chat about all the college dating scene has to offer. Sit back, relax and get ready to laugh out loud listening to these two…

S1E17 College Crushes pt. 1

Jul 03, 2024 55m

Welcome Friends! Jessica and Donna are joining me today to chat about all the college dating scene has to offer. Sit back, relax and get ready to laugh out loud listening to these two lovely ladies!

Limon Squeeze pt. 3

Jun 30, 2024 27m

Welcome Friends! Pedro has been such a great interview! Posting pt. 3 for your listening pleasure! Let's see how LOVE BOMBING from my EX-boss plays out... As always please feel free to leave…

Limon Squeeze pt. 2

Jun 26, 2024 56m

Hi Friends! Part 2 with Pedro is live! Sit back and continue to enjoy the laughs!

S1E15 Limon Squeeze pt. 1

Jun 19, 2024 53m

Hello Everyone and welcome to Awkward Affairs. This week we have a new friend joining me. Pedro is going to share some of his dating experiences, what he's looking for in a potential partner and so…

The Girls Take On The Butcher

Jun 12, 2024 56m

Hi Friends! I'm back with my girls to discuss their take on the Butcher and anything else they want to give me a hard time about! Enjoy the laughs.

S1E13 The Butchers Empty Love

May 08, 2024 1h 1m

*Trigger warning* Hello Friends! Today's episode is about the The Butcher...a man who tried to suck the life out of me through manipulation and mental abuse. I read quotes from the articles below:…

S1E12 Straight Talk:Take 2

May 01, 2024 1h

Julian and Mickey are bacccckkkkkkkk for take 2! Please laugh with me as I ask questions about what they'd rather do when it comes to sex and dating! Sit back, open your favorite beverage and join in…

S1E11 Straight Talk

Apr 24, 2024 1h 12m

Friends! Join me for a hilarious conversation with two great guys...Mickey and Julian. Sit back, relax, and get ready to laugh your ass off while these two guys discuss dating, apps and turn offs.

S1E10 Would you Rather?

Apr 17, 2024 56m

Welcome Friends! Our bestie Lili is back! She is going to ask me a bunch of questions...lets see where this takes us! I'm thinking Lili should come back and do mini-sodes with me on Saturdays! …

S1E9 Do You Remember The Time?

Apr 10, 2024 58m

Hi Friends, welcome to episode 9! Today I've invited my two daughters to chat and reminisce about times they remember me dating and share stories that made me cringe, laugh, and be very thankful that…

S1E8 ...In the Beginning

Apr 03, 2024 52m

Hi Friends! Very excited to share episode 8 with you all! Today I share the stories of guys I met before dating my ex-husband, my marriage, and our divorce.

S1E7 Ep.7: Hookups, Red Flags and Rear Ends Pt. 3

Mar 27, 2024 1h 2m

Welcome Friends! Today is part 3 of the continued discussion of hookups and the stories behind them! Please join me and my friend Thomas as I deep-dive into his adventures of hookups, go-go dancing,…

S1E6 Episode 6: Hookups, Red Flags and Rear Ends Pt. 2

Mar 20, 2024 55m

Welcome to Awkward Affairs! My friend Aaron joins me to talk about his experiences with dating apps, his role-play meet-up, and answers all my questions about dating in the gay community.

S1E5 Hookup, Red Flags, and Rear Ends!

Mar 13, 2024 45m

Welcome friends! It’s Cindy and today I’m discussing hookups and all the awkward details that go with it. So, buckle up and get ready for more mic issues, lots of laughter and me recalling a few of…

S1E4 Episode 4: When Dates Go Wrong

Mar 06, 2024 54m

Lili is back and ready to talk about "when dates go wrong" from her GYM GUY STORY to a first date that lasted 3 hours and oh so much more!

S1E3 Great Expectations: First Dates

Feb 28, 2024 29m

Ahhhh First dates. I've been on 40-50 first dates. Join me as I share a few of my date experiences, my expectations and how a man old enough to be my dad followed me around at Target trying to get me…

Frequently Asked Questions

How many episodes does Awkward Affairs have?

Awkward Affairs has published 23 episodes since February 2024, covering topics in Relationships, Society & Culture.

Is Awkward Affairs still active?

Awkward Affairs is currently dormant with new episodes weekly. Average episode length is 55m.

How do I contact Awkward Affairs for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Awkward Affairs, including email and social media links.

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