Lynnie, Shantal and Gary are back in a new studio! They share a dating fail story discuss the issues with high pressure dates! Plus tackling some of your burning Q/A's! They get into the nitty gritty of PDA - time and place or no limits? What about a smooch post-oral is it hot or not? Plus would they join the mile high...in general boarding? Tune in for juic ... Show More
Jan 28
Dating Someone Who Hates Your Past
When someone can’t accept your past, it can quietly poison the present. In this episode, Claudia, Lynnie, and Gary talk about judgment, insecurity, and what real acceptance actually looks like.
16m 31s
Jan 21
The Fantasy vs. the Reality of Threesomes
Threesomes sound hot in fantasy but the reality can be complicated. Today on Coffee and Cleavage, Lynnie, Claudia, and Gary unpack expectations, emotions, and what people rarely talk about before saying yes.
21m 14s
Dec 2016
Cyber Sex, Latin Lovers, and Happy Endings
With the end of the year fast approaching, I think we could all use a little boost in our sex lives, whether it be your confidence, your health, or your level of kink! Are you wondering how to take your Skype sex to an even hotter level? Does an STI mean the death of your dating ... Show More
53m 40s
Feb 2024
V-Day, TikTok Backlash, And Where The Single Men Are
Happy Valentine’s Day! Today’s episode has something for everyone – lovers, new listeners, singles, and anyone struggling in a situationship. J&J have a dating challenge to share, but first, Jared kicks off with a pep talk for anyone alone on Valentine’s Day. Then, Jordana speaks ... Show More
1h 38m
Mar 2023
Marrying Your High School Sweetheart (w/ Adam Pally)
<p>Comedian <a href="https://www.instagram.com/adam.pally/?hl=en" target="_blank">Adam Pally</a> (<i>101 Places to Party Before You Die, Who Invited Charlie?</i>) chats with Nicole about why an easy relationship is a often sign of a good one, marrying his high school sweetheart, ... Show More
54m 55s
Apr 2021
Sex Stories, Older Men, & STD's w/ Hannah Berner
My guest this week is a standup comedian, cast member on Summer House on Bravo AND host of her podcast Berning in Hell, Hannah Berner! We kickoff the episode by talking about d*ck. Curved d*ck to be exact. She shares her experience with different d*ck sizes and why bigger isn't A ... Show More
1h 1m
<p>It's <em>Why Won't You Date Me</em>'s first married couple guest! Madeline Walter (UCB, <a href="https://itunes.apple.com/us/podcast/definitely-dying/id1110837073?mt=2" target="_blank"><em>Definitely Dying</em></a> podcast) and Ben Greene (UCB, <a href="https://itunes.apple.co ... Show More
