Heartbreak on the L Train: When Love Goes from Dreamy to Disastrous

Well, That Was Awkward

This week, Bree and Mendy share a listener’s unforgettable story of teenage love, heartbreak, and one hilariously awkward date in Brooklyn. From a kiss that could rival a rom-com to a Venmo request that shattered the illusion, this episode is packed with laughs, tears, and relatable moments.

In addition, Bree and Mendy share their own awkward tales of broken laptops, nerd dates, and revisiting books they forgot they’d already read. Whether it’s reliving high school heartbreaks or celebrating the awkwardness of daily life, this episode reminds us that you may be awkward, but you're definitely not alone!

What You’ll Hear:

• A listener’s dramatic story of first love and heartbreak, complete with theater boys, Snapchats, and questionable restaurant choices.
• Bree’s nerd date gone wrong—and why you should always double-check where your laptop is.
• The moment Mendy and Gabe conquered their homebody tendencies… only to encounter an awkward dance floor moment.
• Why theater boys might not always be worth the drama (and when to walk away).
• Breakup advice, the best ice cream for heartbreak, and the joy of awkwardness.

Connect with Us:

• Share your awkward stories (Anonymously – or Not!) in writing or by voicemail at Awkward Sage Media
• Join our Cult of Awkwardness on Facebook – We want to get awkward with you! Facebook Group
• Follow us on Instagram: @awkwardsagemedia
• Buy us a coffee and support this podcast at Buy Me a Coffee

Get a discount on your Monk Manual at Monk Manual using the code AWKWARD.

Friends, this podcast is possible because of your awkward moments -- so please share them with us! Questions? Email us at [e-mail] or hop on over to Instagram and leave us a DM!