Kara's Lipstick Diary artwork

Kara's Lipstick Diary

84 episodes - English - Latest episode: 11 months ago - ★★★★★ - 20 ratings

Apparently I've lived anything but a normal life. That is according to my friends. My stories of dating, sex and life in general tends to make them laugh and for years they've told me I needed to share them with the world. So I decided that in the middle of a pandemic it was a great time to start a podcast about the things that entertain me. So grab a cocktail with us and welcome to the hot mess that is my life as an almost 40 year old single makeup artist living in a college town in Florida. This is Kara's Lipstick Diary.

Sexuality Health & Fitness Arts Fashion & Beauty botox dating fashion makeup sex vibrators
Homepage Apple Podcasts Google Podcasts Overcast Castro Pocket Casts RSS feed

Episodes

Breaking Up with Politeness| Antionette Chanel and Brijana Prooker | Kara's Lipstick Diary | E2:6

March 08, 2022 05:00 - 28 minutes - 19.7 MB

Special anniversary month episode.  Last season we filmed an episode with Antionette Chanel that was inspired by Brijana Prooker article in Elle Magazine titled "It's Time For Women To Break Up With Politeness".  Thanks to the wonderful world of social media we were able to connect with Bri and she agreed to zoom in from California for this special episode where we continue this conversation of putting our own comfort and safety ahead of being "polite".   Link to original article https://ww...

Fun with Good Time Barbie | Daniel Rengering | Kara's Lipstick Diary | E2:5

March 01, 2022 05:00 - 39 minutes - 27.1 MB

Its anniversary month.  We've been officially a show for a year so Daniel Rengering is back on the couch for viewing pleasure.  You all ask the question on the regular... what's up with Kara and Dan?  Are they banging?  Well we decided it was time to answer this and more with questions submitted by viewers on social media.  So sit back with a cocktail and find out all that we have to say about each other while we are well... a tad bit tipsy ourselves.  Here's to some fun with good time Barbi...

Kara's Toy Box Review | Daniel Rengering and Crysta Brown | Kara's Lipstick Diary | E2:4

February 15, 2022 05:00 - 31 minutes - 21.3 MB

In Season 1 Crysta Brown was a guest for the first Sex Toy Review and I decided it was time to have her back to talk about more sex toys.  This time we brought in everyones favorite co-host Daniel Rengering to have a dudes perspective on the toys.  And well... he seemed rather entertained by them and seemed to learn a lot.  Find out which toys Kara loves and the ones she warns not to waste your money on, all with lots of laughs and good cocktail. Bracelets from Hang Ten Handmade Designs  ht...

To Fuck, Fuck Boyz or To Not Fuck, Fuck Boyz? That is the Question | Kara's Lipstick Diary | E2:3

February 01, 2022 05:00 - 30 minutes - 21.3 MB

Season 1 canned wine tasting guest Megan Sapelak is back to talk all things Fuck Boyz.  So should we be mad at Fuck Boyz or do we just need to accept what they are and what they are looking for?  Are we trying to make them into something they aren't and force them to conform to what we want?   And is being with a Fuck Boy bad, if we realize they are there for a fuck not a relationship and can be satisfied with that?  Is a relationship always the goal or can we enjoy a fuck for just a fuck?  ...

Defining Identity | Carrie Wells and Daniel Rengering | Kara's Lipstick Diary | E2:2

January 15, 2022 05:00 - 23 minutes - 16.3 MB

Pronouns...new words for sexual preferences... What does it all mean?  Are you confused?  Should these things be discussed with kids and at school?  That's what Dan and I sit down and discuss with elementary school teacher Carrie Wells who is known of the creating a very inclusive classroom for her students.  We discuss the mental health benefits of letting kids be able to express their identity and giving them the vocabulary to do so.  The vocabulary keeps evolving and we are all trying to ...

Here's to a Cliterate New Year | Dr. Laurie Mitz and Daniel Rengering | Kara's Lipstick Diary | E2:1

January 01, 2022 05:00 - 29 minutes - 20.5 MB

As the ball drops to ring in the new year it's time to talk to the Queen of the Clit herself Dr. Laurie Mitz author of "Becoming Cliterate".  Everyones favorite guest Daniel Rengering of Survivor is back to co-host this first episode of Season 2 as we find out what its like to be a sex therapist and educator and start the conversation about female pleasure and sexuality with her.  We are 100% going to need to have her on again.  I might have fan girled a little with this epic guest.  Make su...

Epic Start: Year in Review | Kara's Lipstick Diary | E1:22

December 15, 2021 05:00 - 34 minutes - 23.6 MB

Wow!!! Never in a million years did I think I would start a podcast / YouTube channel to discuss female pleasure, taste test alcohol and chat about all the things I find interesting and think need to be talked about more.  This year I have found my voice as a 40 year old single makeup artist living in a college town in Florida.  And I have to say it all  feels really amazing.  I've made  amazing new friends and reconnected with friends from my past because of this show.  Thank you all for yo...

Shopping Queen | Connie Craig Carroll | Kara's Lipstick Diary | E1:21

December 01, 2021 05:00 - 29 minutes - 20.2 MB

It's holiday shopping time which is the perfect time to have former HSN host turned HSN jewelry vendor Connie Craig Carroll.  For about a decade Kara worked for a vendor at HSN and got to know Connie when she hosted the shows.  They stayed in contact and now Connie has her very own line and agreed to come on the show to discuss the process of going from selling someone else's products on TV to creating and selling her own products.   EPISODE 21 COCKTAIL RECIPE | Cucumber Mint Mule-Arita 1 o...

Kill...Fuck...Marry - Dan's Take Over | Daniel Rengering | Kara's Lipstick Diary | E1:20

November 15, 2021 05:00 - 58 minutes - 40.5 MB

Birthday Month Continues and #hotcop is back and this time he takes over the show.  Daniel Rengering sits in the host seat and interviews Kara and makes her play a game of Kill...Fuck...Marry.  Watch to see what ridiculousness they discuss. Dan rose to viral fame in 2017 during hurricane irma as #hotcop.  Since then he has appeared on Survivor and Get Away Driver and has graced the covers of multiple romance novels all while still being a cop. Set Flowers Provided by Alachua Flowers and Tu...

Kid Talk | Kara's Little Friends | Kara's Lipstick Diary | E1:19

November 08, 2021 05:00 - 24 minutes - 17.2 MB

Kara may not have kids of her own or ever plan to but kids and Kara get along very well.  When Kara's friend's kids kept asking to watch the show she knew she needed to do an episode just for them.  So for Kara's 40th birthday she's done a fun episode with kids for kids.  Watch what happens when she gives them fancy chocolate milk and gluten free cake pops and tries to interview these adorable little humans.  You never know what kids are going to do or say. EPISODE 19 KIDS COCKTAIL RECIPE |...

Reclaiming My Birthday Suit | Adrienne Fletcher and Kristin Kozelsky | Kara's Lipstick Diary | E1:18

November 01, 2021 04:00 - 57 minutes - 39.6 MB

It's 40th Birthday Month so it's time to pop some bottles and reclaim your birthday suit.  Kara's has two of her besties, Adrienne Fletcher and Kristin Kozelsky,  join the episode and chat about how empowering boudoir photography can be for women wether it's helping with body image after abusive relationships, a sexual assault or an illness or just for fun.  Kara discusses reclaiming her body as her own after being sexually assaulted and how posing for boudoir photos helped her do this.  She...

Airbnb Nightmare | Luke Humphlett | Kara's Lipstick Diary | E1:17

October 28, 2021 04:00 - 59 minutes - 41.1 MB

Catacombs .....  When the producer of my show comes to me and says I need to do an episode with their 18 year old employee for a special halloween episode and that I need to be drunk for it I agree.  The crew would not tell me anything about Luke's adventure beforehand because they want to see my reaction.  Oh was there is a reaction and they were right I did need to be drunk for this story of an Airbnb from hell.   EPISODE 17 COCKTAIL RECIPE | Strawberry Buttercake 1 oz vodka 1 oz. white c...

Airbnb Nightmare | Luke | Kara's Lipstick Diary | E1:17

October 28, 2021 04:00 - 59 minutes - 41.1 MB

Catacombs .....  When the producer of my show comes to me and says I need to do an episode with their 18 year old employee for a special halloween episode and that I need to be drunk for it I agree.  The crew would not tell me anything about Luke's adventure beforehand because they want to see my reaction.  Oh was there is a reaction and they were right I did need to be drunk for this story of an Airbnb from hell.   EPISODE 17 COCKTAIL RECIPE | Strawberry Buttercake 1 oz vodka 1 oz. white c...

Discovering Her Orgasm | Bryn Daylor | Kara's Lipstick Diary | E1:16

October 15, 2021 04:00 - 29 minutes - 20.4 MB

Women often think they have had a orgasm and realize when they have a real orgasm what they have been missing.  My guest Bryn Daylor has gone on a journey in life to find her orgasm and help other women do the same thing along the way.   She spent years of her life trying to fit into the box of a good girl and realized that box didn't fit her needs.  After  attending Burning Man several years ago, with her then husband, she realized it was time to burn down the life she knew and start over. ...

E1:15 | Think Pink | Susie Ulloa | Kara's Lipstick Diary

October 01, 2021 04:00 - 29 minutes - 20.2 MB

October 1st is the start of Breast Cancer Awareness Month.  This month holds a very dear place in my heart because 5 years my dear friend Alanna lost her battle with breast cancer during this month.  To honor her legacy in 2019 I got involved with the local branch of American Cancer Society to see what I could do to help. Susie Ulloa is a breast cancer survivor that I've gotten know over the years.  She has taken what she went through and now helps others battling breast cancer.  I asked he...

E1:14 | Writing Desire | Priscilla Oliveras | Kara's Lipstick Diary

September 15, 2021 04:00 - 28 minutes - 19.7 MB

What is the #1 genre of books sold in America?  Thrillers?  I mean you see those authors being interviewed all the time with the release of a new book.  Nope!  And not by a long shot.  The #1 sold genre of books is romance novels.    Literally 1/3 of all books sold are romance novels with over $1 billion every year.  But yet romance novels still have stigma.  Why?  Maybe because its a genre mostly written by women for women. So I decide it was time to talk about it.  I invited author Prisci...

E1:13 | Events Unleashed | Kristin Zupancic | Kara's Lipstick Diary

September 01, 2021 04:00 - 22 minutes - 15.3 MB

Between working in live theatre and events my entire adult life I have seen everything go wrong.  It's never what you can plan for.  And every time its a total surprise but working in these industries you have to roll with the punches and make it work.   I decided to have my friend and event planner Kristin Zupancic come on the show as a guest to chat about some of the crazy things we have seen while working on events.  From falling cakes to bridesmaid dresses altered to accidentally expose...

E1:12 | Not Your Orgasm Receptacle | Celia Finkelstein | Kara's Lipstick Diary

August 15, 2021 04:00 - 31 minutes - 21.4 MB

In Episode 2 I mention that I didn't know women could masturbate until I over heard an upper classman talking about it in the green room when I was a freshman in college.  Well that upper classman is LA actress and writer Celia Finkelstein.  (You might have seen her in American Horror Story as Gladys or as Margie Emerman in the movie Horrible Bosses.  And she has written for such shows as Shondaland's For the People)  I haven't seen Celia since 2001 when she graduated from Rollins College. ...

E1:11 | Botoxed in Place | Dr. Andrew Martin | Kara's Lipstick Diary

August 01, 2021 04:00 - 24 minutes - 16.9 MB

"I have to go get botox tomorrow."  Often when I say this I get the responses of "Oh you don't need botox" or "Oh if you do that you'll look frozen".  Guess what I've been doing botox regularly for years now.  I do it because botox allows me to breath through my nose and takes away my headaches that I otherwise have every single day.  On top of that its stop wrinkles from forming on my forehead so that's why you say I don't need.  I already have it.  Botox has been tabu for years.  But the t...

E1:10 | Make a Scene | Antionette Chanel | Kara's Lipstick Diary

July 15, 2021 04:00 - 28 minutes - 19.8 MB

Kara recently had a situation where she contacted a friend when something was happening that didn't make her comfortable.  The friend she contacted was Antoinette Chanel who reminded Kara that her comfort and safety comes before someone else's.  She reminded Kara that she had a voice and Kara turned around and used that voice to kick a dude out of her house that was taking a nap In her bed at 8:30pm.  In this episode we talk about how women have been trained to constantly worry about everyon...

1:9 | Dan's Lip"dick" Diary | Dan Rengering | Kara's Lipstick Diary

July 01, 2021 04:00 - 59 minutes - 41 MB

The first male guest on Kara's Lipstick Diary, Dan Rengering of viral #hotcop fame and Survivor, is back for another episode and this time he turns the tables on Kara and interviews her more than she interviews him.  She might have been a little tipsy to allow this to happen.  While they chat about bad sex and dating, they taste test 27 canned cocktails and discover that well, most of them aren't that great.  The conversation though is great and so instead of just bantering for 30 minutes th...

1:8 | On Fleek | Nikki Naylor | Kara's Lipstick Diary

June 15, 2021 04:00 - 29 minutes - 20.5 MB

As a makeup artist Kara is asked about eyebrows and eyelashes all the time.  She decided for her first beauty episode that this is what she would focus on and invited brow and lash queen herself Nikki Naylor of Beauty Lounge and Co. to come on air with her.  Nikki plucks Kara's brows on air.  Then Kara fills them in with her favorite pencil, gives some mascara tricks and shows how to apply a strip of lashes.  Then she and Nikki discuss some of the other brow and lash options out there from m...

E1:7 | Fostering Strength | Betsy Foster | Kara's Lipstick Diary

June 01, 2021 04:00 - 31 minutes - 21.9 MB

Kara invites her bestie Betsy Foster on the show to discuss fitness, body image and more.  Betsy is a virtual personal trainer with her company Fostering Strength.  Kara and Betsy discuss that there's more to fitness than just being skinny.  Delve into social pressures to be thin and the unhealthy habits that people can fall into including Kara's past with eating disorders. Betsy discusses having healthy expectations when raising a daughter that don't just focus on being thin. For all the l...

E1:6 | Dating Disasters | Kara Wassman | Kara's Lipstick Diary

May 15, 2021 04:00 - 26 minutes - 18.3 MB

Kara invites her bestie name twin Kara Wassman on the show to discuss dating disasters.  Winslow has been single her entire life.  Wassman is back on the dating scene after a recent divorce as a mom of two.  What's like to be middle aged trying to date in a college town.  Winslow always ends up with crazy ones.  Wassman with the Eeyores.  Maybe one day they will figure out how to navigate the ways of dating and relationships  For all the latest contests and happening behind the scenes: Face...

1:5 | Viral Survivor | Daniel Rengering | Kara's Lipstick Diary

May 01, 2021 04:00 - 29 minutes - 20.4 MB

OMG there's a boy on Kara's Lipstick Diary.  That's right Kara's guest this episode is none other than #hotcop himself.  Oh wait he actually has a real name.   Daniel Rengering came on the episode to talk about what it was like to unexpectedly go viral when his job at the Gainesville Police Department posted a photo of him in 2017 during Hurricane Erma that went viral.  From there he started modeling for the covers of romance novels and appeared on Season 37 David vs. Goliath of Survivor on ...

E1:4 - Screw Social Expectations | Natalie Woods | Kara's Lipstick Diary

April 15, 2021 04:00 - 29 minutes - 20.4 MB

Kara Winslow and her guest Natalie Woods discuss not fitting into the typical social expectations of being a woman.  From not have a traditional wedding or wedding at all to deciding to not have children.  The reactions they have received from friends and family and some of the reasons they didn't want to fit into these social constructs of what we are told women are supposed to want.    For all the latest contests and happening behind the scenes: Facebook: https://www.facebook.com/Karas-L...

Wine is My Spirit Animal

April 01, 2021 04:00 - 30 minutes - 21.2 MB

Kara and her guest Megan taste test 19 canned wines in 30 minutes.  Find out which they liked, which were total nos and what challenge her guest accepted.  Much tipsy giggling ensues.  

E1:3 | Wine is My Spirit Animal | Megan Sapelak | Kara's Lipstick Diary

April 01, 2021 04:00 - 30 minutes - 21.2 MB

Kara and her guest Megan Sapelak taste test 19 canned wines in 30 minutes.  Find out which they liked, which were total nos and what challenge her guest accepted.  Much tipsy giggling ensues.  For all the latest contests and happening behind the scenes: Facebook: https://www.facebook.com/Karas-Lipstick-Diary-Podcast-102269531874932  Instagram: https://www.instagram.com/karaslipstickdiary/ To view the antics subscribe to the YouTube channel: https://www.youtube.com/channel/UCE2PJP9HbooCgKSD...

E1:3 | Wine is My Spirit Animal | Megan Sapelak | Kara's Lipstick Diary

April 01, 2021 04:00 - 30 minutes - 21.2 MB

Kara and her guest Megan Sapelak taste test 19 canned wines in 30 minutes.  Find out which they liked, which were total nos and what challenge her guest accepted.  Much tipsy giggling ensues.  For all the latest contests and happening behind the scenes: Facebook: https://www.facebook.com/Karas-Lipstick-Diary-Podcast-102269531874932  Instagram: https://www.instagram.com/karaslipstickdiary/ To view the antics subscribe to the YouTube channel: https://www.youtube.com/channel/UCE2PJP9HbooCgKSD...

Feel the Buzz

March 15, 2021 04:00 - 27 minutes - 19.1 MB

Female Pleasure - a tabu subject that is even often ignored in sexual eduction.  We discuss  this along with reviewing sex toys.

E1:2 | Feel the Buzz | Crysta Brown | Kara's Lipstick Diary

March 15, 2021 04:00 - 27 minutes - 19.1 MB

Female Pleasure - a tabu subject that is even often ignored in sexual eduction.  Kara and her guest Crysta Brown discuss  this along with reviewing sex toys.  Their favorite vibrator for sure is the Womanizer.   For all the latest contests and happening behind the scenes: Facebook: https://www.facebook.com/Karas-Lipstick-Diary-Podcast-102269531874932  Instagram: https://www.instagram.com/karaslipstickdiary/ To view the antics subscribe to the YouTube channel: https://www.youtube.com/channe...

E1:1 | Meet Kara | Julie Mishoe | Kara's Lipstick Diary

March 01, 2021 05:00 - 27 minutes - 18.6 MB

Get to know Kara on her first episode with her guest Julie Mishoe, that has known her for over 25 years and can tell you all the embarrassing things from her youth. As well as a discussion of growing with 90s fashion and watching it all come back full circle. For all the latest contests and happening behind the scenes: Facebook: https://www.facebook.com/Karas-Lipstick-Diary-Podcast-102269531874932  Instagram: https://www.instagram.com/karaslipstickdiary/ To view the antics subscribe to the...

Meet Kara

March 01, 2021 05:00 - 27 minutes - 18.6 MB

Get to know Kara on her first episode with a guest that has known her for over 25 years and can tell you all the embarrassing things from her youth.

What to expect from Kara's Lipstick Diary - Show Trailer

February 25, 2021 00:00 - 43 seconds - 529 KB

Apparently I've lived anything but a normal life.  That is according to my friends.  My stories of dating, sex and life in general tends to make them laugh and for years they've told me I needed to share them with the world.  So I decided that in the middle of a pandemic it was a great time to start a podcast about the things that entertain me.  So grab a cocktail with us and welcome to the hot mess that is my life as an almost 40 year old single makeup artist living in a college town in Flo...