DiscoverGood GuysDating at 40 & Other Olympic Sports with Jared Freid
Dating at 40 & Other Olympic Sports with Jared Freid

Dating at 40 & Other Olympic Sports with Jared Freid

Update: 2026-01-26
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The podcast begins with a vivid account of attending a Chicago Bears game, detailing the intense atmosphere, family involvement, and the emotional highs and lows. This experience is humorously contrasted with a social media mishap where audio was muted on Instagram stories. The conversation then delves into post-game celebrations, including a birthday dinner at Gibson's in Chicago, known for its lively ambiance. The discussion touches upon personal wellness journeys, referencing GLP-1, and revisits the immersive Chicago dining experience. A past anecdote about the Steve Harvey show and a trip to Chicago involving hotel and weather experiences are shared. The hosts discuss game day attire, fan etiquette, and the surprising knowledge of the Bears' fanbase, even during a losing streak. The legendary 1985 Bears team and coach Mike Ditka are fondly remembered. The atmosphere at the game is compared to a college setting, fostering unity. The conversation shifts to sports fandom loyalty, particularly concerning the New York Jets through the lens of Jared's father-in-law, Ken O'Brien, and the New York Knicks. The podcast features sponsored segments on Momentus creatine for cognitive function and Hero Bread for low-carb options, as well as Hims for ED treatment. The hosts explore dating preferences, emphasizing "green flags" like shared humor and passion, while also discussing millennial nostalgia and online drama. They humorously dissect dating scenarios involving menu choices and the impact of differing preferences like veganism. The complexities of intimacy on a first date and the importance of humor in long-term relationships are explored. The discussion likens a good date to an improv partnership, highlighting the dangers of insecurity and competition. Pre-date awareness and the potential insult of someone claiming to have never heard of you are debated. The hosts also touch upon the opposite extreme of over-fandom and the unspoken nature of first meetings. They ponder why some people downplay egos and share personal stories about meeting their wives. Generational differences in media awareness and potential "red flags" in dating, such as disliking popular cultural phenomena, are discussed. The concept of the "man in the arena" is used to frame criticism, differentiating between thoughtful and blind hatred, and introducing the idea of "Fuck That Guy" (FTG) mode. The dynamics of couple friendships and the perceived difficulty men face in making new friends as adults are explored. Dating at 40 is discussed, emphasizing the importance of understanding life experiences. The hosts dismiss the notion of a "male loneliness plight" as "loser talk." Parental social interactions and the unknowns of commitment are also touched upon. The conversation returns to dating differences in the 40s, the truth of lived experiences, and the intimacy found in sharing life stories. Readiness for a relationship is linked to the ability to articulate one's life story. Age flexibility in dating and the challenges of being single later in life are acknowledged. Peculiar hypothetical scenarios involving older men and their wives are discussed, along with the tendency for people to share secrets with the hosts. The hosts note that people approach them with discussions related to their known passions and the effort put into crafting thoughtful public statements. They describe receiving unsolicited stories, often prefaced with "Jared, you'll love this," which can precede offensive content. Sponsored segments by Kajava for outdoor wellness and Shopify for business launches are featured. The podcast concludes with discussions on celebrity look-alikes, perceptions of celebrity heights, and a humorous anecdote about encountering Adrian Grenier. The hosts delve into the common surprise at celebrity heights and navigate conversations about height in dating. Golf swing mechanics are discussed, focusing on weight distribution and hitting down versus up on the ball. Jared promotes his upcoming projects, including shows, a book, and his podcast. The recurring segment "What Are Your Nuts?" covers extreme airline loyalty and a humorous anecdote about a man discussing his Costa Rica trip at Equinox. The podcast wraps up with a call for listener reviews and subscriptions.

Outlines

00:00:00
Game Day, Social Media, and Chicago Vibes

The podcast kicks off with Jared Freed sharing his intense experience at a Chicago Bears game, complete with family involvement and the emotional rollercoaster of the event. This is humorously juxtaposed with a social media mishap where his Instagram stories lacked audio, leading to a lack of engagement. The conversation then shifts to a memorable family day at the game followed by a birthday celebration at Gibson's steakhouse in Chicago, known for its vibrant atmosphere and martinis.

00:06:42
Wellness, Past Trips, and Sports Fandom

The discussion touches on personal wellness journeys, referencing GLP-1, and revisits the immersive Chicago dining experience at Gibson's. Jared shares a past trip to Chicago involving the Steve Harvey show and a memorable setup for his then-girlfriend. The hosts discuss their experiences with Chicago's cold weather and hotel stays. The conversation then delves into game day attire, fan etiquette, and the surprising knowledge of the Bears' fanbase, even during a losing streak. The legendary 1985 Bears team and coach Mike Ditka are fondly remembered, with the game atmosphere compared to a college setting fostering unity. The focus shifts to sports fandom loyalty, particularly concerning the New York Jets through the lens of Jared's father-in-law, Ken O'Brien, and the New York Knicks, exploring the fragmentation of fandom in New York.

00:14:56
Dating, Nostalgia, and Relationship Green Flags

The podcast features sponsored segments on Momentus creatine for cognitive function and Hero Bread for low-carb options. The hosts explore dating preferences, emphasizing "green flags" like shared humor and passion, while also discussing millennial nostalgia and online drama. They humorously dissect dating scenarios involving menu choices and the impact of differing preferences like veganism. The complexities of intimacy on a first date and the importance of humor in long-term relationships are explored. The discussion likens a good date to an improv partnership, highlighting the dangers of insecurity and competition. Pre-date awareness and the potential insult of someone claiming to have never heard of you are debated. The hosts also touch upon the opposite extreme of over-fandom and the unspoken nature of first meetings. They ponder why some people downplay egos and share personal stories about meeting their wives.

00:26:58
Generational Differences, Red Flags, and Criticism

Generational differences in media awareness and potential "red flags" in dating, such as disliking popular cultural phenomena, are discussed. The hosts express a dislike for individuals who intentionally go against popular consensus. The concept of the "man in the arena" is used to frame criticism, differentiating between thoughtful and blind hatred, and introducing the idea of "Fuck That Guy" (FTG) mode. The dynamics of couple friendships and the perceived difficulty men face in making new friends as adults are explored.

00:36:50
Dating at 40, Life Stories, and Social Interactions

Dating at 40 is discussed, emphasizing the importance of understanding life experiences and how they have shaped individuals. The hosts dismiss the notion of a "male loneliness plight" as "loser talk." Parental social interactions and the unknowns of commitment are also touched upon. The conversation returns to dating differences in the 40s, the truth of lived experiences, and the intimacy found in sharing life stories. Readiness for a relationship is linked to the ability to articulate one's life story. Age flexibility in dating and the challenges of being single later in life are acknowledged. Peculiar hypothetical scenarios involving older men and their wives are discussed, along with the tendency for people to share secrets with the hosts. The hosts note that people approach them with discussions related to their known passions and the effort put into crafting thoughtful public statements. They describe receiving unsolicited stories, often prefaced with "Jared, you'll love this," which can precede offensive content.

00:45:12
Business, Celebrity Perceptions, and Golf Insights

Sponsored segments by Kajava for outdoor wellness and Shopify for business launches are featured. The podcast concludes with discussions on celebrity look-alikes, perceptions of celebrity heights, and a humorous anecdote about encountering Adrian Grenier. The hosts delve into the common surprise at celebrity heights and navigate conversations about height in dating. Golf swing mechanics are discussed, focusing on weight distribution and hitting down versus up on the ball. Jared promotes his upcoming projects, including shows, a book, and his podcast.

00:56:55
Extreme Loyalty and Show Wrap-up

The recurring segment "What Are Your Nuts?" covers extreme airline loyalty and a humorous anecdote about a man discussing his Costa Rica trip at Equinox. The podcast wraps up with a call for listener reviews and subscriptions.

Keywords

Chicago Bears Game


A professional American football game featuring the Chicago Bears. This includes the atmosphere, fan culture, and the emotional experience of attending such an event, especially during playoff implications.

Social Media Engagement


The level of interaction and attention a social media post receives. This can include likes, comments, shares, and views, and how a lack of audio on a video can impact engagement.

Gibson's Restaurant Experience


A dining experience at Gibson's, a well-known steakhouse, characterized by its lively atmosphere, classic Chicago vibe, and specific menu items like martinis and steaks.

Sports Fandom Loyalty


The dedication and commitment fans show to their sports teams, even through periods of losing or underperformance, and the cultural significance of this loyalty.

Dating Preferences and Green Flags


Factors that make a positive impression on a date, such as shared interests, passions, a good sense of humor, and genuine opinions, often referred to as "green flags."

Millennial Nostalgia


A sentimental longing or wistful affection for the past, specifically for the culture and trends of the millennial generation, often evoked by media or shared experiences.

"Man in the Arena" Quote


A quote by Theodore Roosevelt emphasizing the value of action and participation over criticism from the sidelines, often used to discuss courage and vulnerability.

"Fuck That Guy" Mode (FTG)


An initial, often subconscious, negative reaction or judgment towards a person, which may later be re-evaluated or overcome with more information or understanding.

Making New Friends in Adulthood


The process and challenges of forming new friendships after childhood or young adulthood, often involving work, shared activities, or social circles.

Dating at 40


The experience of dating in one's 40s, characterized by individuals having more established life stories, experiences, and potentially more complex emotional landscapes.

Celebrity Height Perceptions


The common tendency for people to have preconceived notions about celebrities' heights and to be surprised when they encounter them in person, whether they are taller or shorter than expected.

Golf Swing Mechanics


Focuses on the physical movements and techniques involved in hitting a golf ball, including weight transfer, ball striking (downward vs. upward), and stance. Proper mechanics are crucial for consistency and power.

Airline Loyalty Programs


Systems used by airlines to reward frequent flyers with benefits like upgrades, lounge access, and miles. These programs encourage customer retention but can sometimes lead to irrational travel decisions.

"What Are Your Nuts?"


A recurring segment where hosts discuss peculiar behaviors or extreme loyalties that they find baffling or excessive, often related to everyday choices or obsessions.

Social Media Presence


Refers to an individual's activity and engagement on platforms like Instagram and TikTok. For comedians and podcasters, it's a key tool for promotion, audience interaction, and brand building.

Q&A

  • What was Jared's experience like at the Chicago Bears game?

    Jared described the game as an intense emotional rollercoaster, with his family deeply involved in the team. He highlighted the playoff atmosphere and the pressure his brother, on the coaching staff, felt.

  • Why was Jared disappointed with his Instagram stories from the game?

    Jared was disappointed because he realized the audio on his Instagram stories was muted, meaning no one could hear what he was saying, and worse, no one seemed to notice or care.

  • What are some of the "green flags" discussed in dating?

    Green flags include having a passion for something, possessing strong opinions, a shared sense of humor, and the ability to make each other laugh. Genuine enthusiasm and a willingness to share one's story are also valued.

  • How do the hosts differentiate between genuine dislike and jealousy?

    They suggest that while genuine dislike can stem from specific reasons, a blanket statement like "I hate Taylor Swift" might indicate jealousy or a desire to appear unique, rather than a well-founded opinion.

  • What is the "Man in the Arena" concept and how does it relate to online criticism?

    The "Man in the Arena" quote emphasizes that it's easier to criticize those who are actively participating and taking risks than to be one of them. This applies to online criticism, where people often attack those putting themselves out there.

  • What is "Fuck That Guy" (FTG) mode?

    FTG mode is described as an initial, often subconscious, negative reaction or judgment towards a person. The hosts suggest acknowledging this mode and then working to overcome it with more understanding.

  • What are the challenges of making new friends as an adult?

    The hosts discuss how making new friends as an adult can be difficult, with one host noting that his first new friend in two decades was made recently, highlighting the rarity of such connections.

  • How does dating at 40 differ from dating in one's 20s and 30s?

    Dating at 40 involves individuals with more established life stories and experiences. The focus shifts to understanding their past and how it has shaped them, rather than just future aspirations.

  • What is the significance of someone being able to tell their life story on a first date?

    The hosts believe that being able to articulate one's life story on a first date signifies readiness for a relationship. It shows self-awareness and an understanding of how past experiences have led them to the present.

  • What is the common reaction when people meet celebrities in person regarding their height?

    A frequent reaction is surprise at a celebrity's height, with people often saying, "Wow, you're much taller/shorter than I thought," indicating a discrepancy between perception and reality.

  • What is the key difference in hitting the ball with irons versus drivers in golf?

    With irons, you're supposed to hit down on the ball, and your weight should be forward. For drivers, you're supposed to hit up on the ball, and your weight should be neutral.

  • What are some of Jared's upcoming projects?

    Jared is promoting his shows in New York, Toronto, and Boston, his new book "Walking Red Flag," and his daily podcast, "The J-Train Podcast."

  • What is the "What Are Your Nuts?" segment about?

    This segment features discussions on extreme behaviors or loyalties, such as excessive dedication to an airline, that the hosts find unusual or irrational.

  • Why did the man at Equinox mention his trip to Costa Rica?

    The hosts speculate he was either lonely and seeking conversation or trying to "cruise" or pick someone up in the gym's social environment.

  • How can listeners support the podcast?

    Listeners are encouraged to rate, review, and subscribe to the podcast on their preferred platform, and to leave reviews, which may be read on the show.

Show Notes

Mazel morons! Jared Freid touches down (literally) to talk the Bears playoff, his “slapstick idiot brother” era, the insanity of dating at 40, and the man who hit 2 million Delta miles… in Delta Comfort. Plus, we dive into improv-compatible partners, why couples’ friends are harder to find than spouses, and Jared’s inch-and-a-half uneven legs becoming the key to his golf swing. What, are ya nuts? 


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Dating at 40 & Other Olympic Sports with Jared Freid

Dating at 40 & Other Olympic Sports with Jared Freid

Dear Media