Ever wondered what it’s like to ditch a high-powered finance career for life as a stand-up comedian?

Meet Matt Broom—a former Morgan Stanley executive who traded suits for stage lights and now brings his sharp wit and wild stories to the mic. From date-night crowds to navigating the world of comedy groupies (yep, they’re called "chuckle fuckers"), Matt spills what it’s really like to live life one punchline at a time. Spoiler: it’s a lot less rock ‘n’ roll than you’d think, and way more hustle.

Relationships are tricky enough, but what happens when you toss a third person into the mix? We dive headfirst into the world of polyamory with stories straight from people who’ve lived it. From marriages that grew into throuples to the emotional rollercoaster of managing jealousy (and calendars), we unpack the chaos, charm, and unexpected lessons of unconventional love. Oh, and one of our hosts gets real about their own trust issues—you won’t want to miss that.

Of course, it wouldn’t be a dating episode without some hilarious misadventures. We’ve got bathroom blunders, first date disasters, and one truly jaw-dropping catfishing story that’ll leave you clutching your phone a little tighter. Add in some quirky talents (unicycling, anyone?) and heart-to-heart convos about dating at 50, and you’ve got yourself one heck of a ride.

Whether you’re here for the love lessons, the laughs, or just a good story, this episode’s got you covered!

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Ever tried dating after putting your career and personal growth first for a while? Well, our guest Ashley is jumping back into the dating scene with a fresh outlook and a clear idea of what she’s after.

From funny thoughts on deal-breakers (like seriously, dental hygiene, guys!) to real talk about spotting red flags, Ashley’s sharing her journey of balancing what she wants in a partner with finding a meaningful connection.

Ashley’s got some seriously fun stories from her time in the high-profile sports world, where finding a genuine partner is like looking for a needle in a haystack of glitz and glam. She spills the tea on how some relationships get caught up in superficial stuff, especially in the sports and media world, and how athletes have their own unique challenges when it comes to love.

But don’t worry, we’re not all about the drama. We also chat about how to keep relationships strong and exciting—from setting realistic expectations on first dates to keeping the romance alive with simple, sweet gestures. Whether you’re dipping your toes into the dating pool or trying to keep the spark going in a long-term relationship, Ashley’s got some hilarious and real advice that’ll keep you grounded and true to yourself.

This episode is packed with laughs, stories, and some seriously good relationship tips. Whether you're dating, married, or just in the mood for some real talk, you won’t want to miss this one!

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Get ready to meet Swingin’ Steve—an adventurous, free-spirited guy who turned jealousy into a full-blown lifestyle of thrills and connection. His journey into the swinger community kicked off with a chance encounter with an older woman, and it’s been one wild ride ever since! 

Steve’s got stories that’ll keep you laughing and questioning everything you thought you knew about relationships—from leaving his number on a stranger’s car in the rain to embracing the world of open relationships. His take on living life without judgment is as refreshing as it is hilarious. 

If you're into someone who’s got a knack for fun, a healthy dose of spontaneity, and a no-holds-barred attitude toward unconventional relationships, then this episode is for you! 

So if you are single and ready for some laughs, juicy stories, and a new perspective on love, Steve’s definitely the guy to show you how to break free from the norm. 

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Are you ready to meet Melissa—a radiant, independent woman in her 40s who knows what she wants and isn’t afraid to go for it? After navigating life’s ups and downs, including a divorce and a cancer diagnosis, Melissa is reclaiming her sparkle and stepping boldly into the dating world.

She’s smart, funny, and unapologetically confident, bringing a zest for life and a love for meaningful connections. Melissa isn’t just about dinner dates and small talk—she’s all about spontaneous adventures, authentic conversations, and that perfect mix of chemistry and depth.

If you’re into a woman who values independence, embraces life’s challenges with grace, and can make you laugh over a good story, this episode is for you. Melissa shares her thoughts on love, relationships, and why she’s holding out for someone who can match her energy and spark.

But hey gents! Think you’ve got what it takes to join Melissa on her quest for love? Tune in and see why she’s the catch you didn’t know you were waiting for!

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

In today's episode, we delve into the turbulent waters of modern dating, sharing our personal encounters with being stood up, catfished, and ghosted. We explore the complexities of communication, honesty, and the importance of navigating these relationships with awareness and humor.

• Reflecting on the shock of being stood up 
• Discussing the embarrassment and emotional toll of waiting 
• The fears surrounding confrontation in dating 
• Experiences of bailing on dates 
• The struggle between honesty and avoidance 
• Positive feedback from being transparent after dates 

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Meet our sizzling single Steve and hear our thoughts on what not to do and say on a first date.

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Meet our sizzling single Chuck, and hear our thoughts on dating in this decade.

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Meet our sizzling single Brad and hear our thoughts on marriage in this day and age.

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Meet our sizzling single Momo and hear our thoughts on infidelity.

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!

Meet our sizzling single Brooks and hear our thoughts on dating OFF the apps.

A big shoutout to our amazing sponsor, Tactical Tax Strategies! You can check them out at steptax.com. Remember, we drop your drawers, and they drop the tax—making life a little smoother for everyone. Thanks for keeping us covered!