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Awkward Affairs
Cindy Ussery
23 episodes
22 hours ago
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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Relationships
Society & Culture
RSS
All content for Awkward Affairs is the property of Cindy Ussery and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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.
Show more...
Relationships
Society & Culture
Episodes (20/23)
Awkward Affairs
Love, Hayli

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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8 months ago
1 hour 51 minutes 29 seconds

Awkward Affairs
Welcome Back!

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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8 months ago
52 minutes 8 seconds

Awkward Affairs
WWCD What Would Cindy Do?

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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1 year ago
1 hour 1 minute 49 seconds

Awkward Affairs
College Crushes pt. 2

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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1 year ago
29 minutes 26 seconds

Awkward Affairs
College Crushes pt. 1

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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1 year ago
55 minutes 48 seconds

Awkward Affairs
Limon Squeeze pt. 3

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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1 year ago
27 minutes 36 seconds

Awkward Affairs
Limon Squeeze pt. 2

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

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1 year ago
56 minutes 19 seconds

Awkward Affairs
Limon Squeeze pt. 1

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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1 year ago
53 minutes 45 seconds

Awkward Affairs
The Girls Take On The Butcher

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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1 year ago
56 minutes 58 seconds

Awkward Affairs
The Butchers Empty Love

*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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1 year ago
1 hour 1 minute 9 seconds

Awkward Affairs
Straight Talk:Take 2

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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1 year ago
1 hour 26 seconds

Awkward Affairs
Straight Talk

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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1 year ago
1 hour 12 minutes 2 seconds

Awkward Affairs
Would you Rather?

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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1 year ago
56 minutes 35 seconds

Awkward Affairs
Do You Remember The Time?

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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1 year ago
58 minutes 29 seconds

Awkward Affairs
...In the Beginning

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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1 year ago
52 minutes 5 seconds

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

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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1 year ago
1 hour 2 minutes 39 seconds

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

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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1 year ago
55 minutes 35 seconds

Awkward Affairs
Hookup, Red Flags, and Rear Ends!
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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1 year ago
45 minutes 3 seconds

Awkward Affairs
Episode 4: When Dates Go Wrong

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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1 year ago
54 minutes 53 seconds

Awkward Affairs
Great Expectations: First Dates

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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1 year ago
29 minutes 39 seconds

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.