Awkward Affairs

Awkward Affairs

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.

Episodes

February 20, 2025 111 mins

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 me for a few laughs, a few gasps and as always a bit of fun!

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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 life and why I’m focused on a soft life. I’m very excited for you to join me!

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July 10, 2024 61 mins

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 laughs and hopefully equally good advice!


This will be my last episode for a while....its time to take a break. I've had so much fun!

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July 3, 2024 29 mins

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 lovely ladies!

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July 3, 2024 55 mins

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!

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June 29, 2024 27 mins

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 questions or comments here or on Instagram @awkwardaffairspodcast

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June 26, 2024 56 mins

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

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June 19, 2024 53 mins

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 much more!

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June 12, 2024 56 mins

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.


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May 8, 2024 61 mins

*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:

Sternberg's Triangular Theory of Love | 8 Types of Love (simplypsychology.org)


What is Empty Love? - Relationships - eNotAlone

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May 1, 2024 60 mins

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 the laughs!

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April 24, 2024 72 mins

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.

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April 17, 2024 56 mins

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! Thoughts?

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April 10, 2024 58 mins

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 I'm no longer dating those people.

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April 3, 2024 52 mins

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.

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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, and his clubbing days!

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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.

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March 13, 2024 45 mins
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 my ridiculous hookups.
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March 6, 2024 54 mins

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!

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February 28, 2024 29 mins

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 to join him for dinner.

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