Valentine’s Day is just around the corner, and the listeners are feeling ticked off! Jared breaks down the holiday chaos, starting with a rant about CVS’s fever dream of plush dolls, cult-like flower pots, and junk chocolate destined for landfills.

Then, it's on to the dating dilemmas:

💔 A listener whose boyfriend is ditching her for a guys’ weekend despite her love for all things corny and romantic.

💡 Jared offers thoughtful advice on handling disappointment when communication feels one-sided.

💘 Another listener grapples with mixed signals from a no-strings-attached fling suddenly going full Valentine's mode. Should she say yes to dinner and flowers or keep things casual? Jared delivers his signature insight on how to set boundaries without burning bridges.

It’s an episode filled with frustration, advice, and a whole lot of heart — just in time for Valentine’s Day.

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Hero Bread Support the show and get 10% off your Hero Bread orde with code JTRAIN at https://www.hero.co

MeUndies Support the show and get 20% off your first MeUndies order, plus free shipping with code feather at https://www.meundies.com/feather

Indochino Support the show and get 20% off of any Indochino purchase of $499 or more. Use code JTRAIN at https://www.indochino.com

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

This week’s Mailbag Monday brings two wild listener stories that’ll have you shaking your head and laughing out loud. First, Jared responds to a med school listener whose whirlwind romance with the class clown took a sharp turn into weirdsville. From bizarre family dynamics involving a touchy sibling to a jaw-dropping white coat ceremony reveal, this story is packed with twists, including a moment that made her walk out for good. But now that she's trying to stay civil, friends say she's being too nice—what should she do?

Next up, a listener seeks advice on some late-night Instagram behavior from her friend’s husband. Picture this: 2 AM likes on photos dating back to 2019… and then another spree at 4 AM, this time digging all the way to 2016. Is this classic "tap the glass" flirting? Should she tell the wife, confront him, or steer clear entirely? Jared breaks it all down with thoughtful advice, sharp humor, and insights you won’t want to miss.

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Hero Bread Support the show and get 10% off your Hero Bread orde with code JTRAIN at https://www.hero.co

MeUndies Support the show and get 20% off your first MeUndies order, plus free shipping with code feather at https://www.meundies.com/feather

Indochino Support the show and get 20% off of any Indochino purchase of $499 or more. Use code JTRAIN at https://www.indochino.com

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

Jared Freid is back for Pop Culture Thursday, diving into the hottest stories from Page Six! This week, Jared reacts to Kanye West’s wife causing a stir by getting naked in public — is it bold fashion or just too much? Then, it’s time to discuss the drama swirling around the Real Housewives of New York and what fans can expect next season. Plus, Brody Jenner is making headlines with some surprising revelations about his family life.

To top it all off, Jared breaks down the buzz around the 2025 Grammy Awards, including predictions, performances to watch for, and a few eyebrow-raising nominations. Sit back, relax, and enjoy Jared’s hilarious takes on all things pop culture!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Green Chef Support the show 50% off your 1 st Green Chef box with code JTRAINFREE at https://www.greenchef.com/JTRAINFREE

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

This week, Jared Freid brings the energy straight from the glitzy heart of Beverly Hills for another Chit Chat Wednesday! Back by popular demand is his good friend and expert gambler, Thunder Dan, who’s ready to break down the highs and lows of their preseason NFL predictions 🏈🙌 From unexpected division champs to MVP picks that missed the mark, the duo laughs at their bold takes—and a few surprisingly accurate calls.

With the Super Bowl right around the corner, Jared and Dan dive into wild prop bets, debating everything from the classic coin toss (“Tails never fails!”) to the Gatorade color and national anthem length. But it’s not just about football. Dan shares his post-Super Bowl plans: a family trip to Disney, where he’s either gliding through the Lightning Lane or suffering with the common folk. Jared, naturally, has strong opinions on that.

As they break down game strategies, Mahomes' growing legacy, and those nail-biting two-yard plays, Jared and Dan serve up hot takes and plenty of laughs. Whether you're here for betting insights, Super Bowl prep, or just hilarious banter about surviving Disney with kids, this episode has it all.

Tune in for the picks, stay for the laughs—and don’t forget to place your bets!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Green Chef Support the show 50% off your 1 st Green Chef box with code JTRAINFREE at https://www.greenchef.com/JTRAINFREE

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

In this episode of The JTrain Podcast, Jared lets the feathers fly as listeners share their most aggravating complaints:

First, Jared commiserates with a listener fed up with hotels that still don’t have smart TVs. In 2025, flipping through local channels shouldn't be a thing when you're paying $140 a night. Jared has some advice for making your next hotel stay smarter.

Next, a listener vents about dog owners bringing their unchill pups into restaurants and stores. Jared breaks down where dog etiquette is crossing the line and wonders if inconsiderate dog owners are just oblivious—or selfish.

Then, a listener is tired of friends guilt-tripping them about following POTUS on Instagram. Jared offers his take on social media self-righteousness and the value of staying informed straight from the source.

Finally, Jared weighs in on a dinner dilemma. Should one friend’s budget-conscious stance dictate the vibe of a group night out? Jared delivers thoughtful advice on balancing financial differences without ruining the evening.

Feather, feather—it's time to get ticked off and laugh it off!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

DraftKings Support the show by downloading the DraftKings Sportsbook app and using code JTRAIN. New customers can bet $5 to get $200 in bonus bets instantly.

Hero Bread Support the show and get 10% off your Hero Bread order with code JTRAIN at https://www.hero.co

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

Mailbag Monday! 💌 Jared answers three listener emails packed with relatable dating frustrations:

First, a listener wonders why guys keep asking for her Instagram handle before meeting in person. Jared breaks down the psychology behind this common dating app move and offers tips on politely setting boundaries without killing the vibe.

Next, a "too friendly gal" shares her discouragement after a ski trip turned awkward when a flirtation fizzled. Jared dives into the nuances of being friend-zoned, why it happens, and how to project romantic energy without changing who you are.

Finally, a listener asks if she should turn up the flirting with her new, reliable boyfriend. Jared provides advice on navigating the honeymoon phase and finding the balance between polite connection and playful chemistry.

Feather, feather! Tune in for Jared’s thoughtful advice, insightful dating takes, and, as always, plenty of laughs😂

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

DraftKings Support the show by downloading the DraftKings Sportsbook app and using code JTRAIN. New customers can bet $5 to get $200 in bonus bets instantly.

Hero Bread Support the show and get 10% off your Hero Bread order with code JTRAIN at https://www.hero.co

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

On this week’s Pop Culture Thursday, Jared Freid dives into the hottest headlines and gives his unfiltered takes on all things trending. From Matt James and Rachael Kirkconnell’s surprising breakup to Amy Schumer clapping back at trolls, Jared shares his hilarious and relatable perspective on these celebrity moments. Plus, what’s Martha Stewart’s latest move that has everyone talking? Tune in for Jared’s unique blend of humor and pop culture commentary that’ll have you laughing from start to finish!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Factor Support the show and get 50% off your first Factor box, plus free shipping. Use the code JTRAIN50OFF at https://www.factormeals.com/JTRAIN50OFF

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

Jared is back for a special Chit Chat Wednesday, and this week he’s joined by comedian Liza Treyger, fresh off the release of her Netflix special Night Owl. They dive right into the wild ride of creating a comedy special — from dealing with creative pressures to staying authentic when the stakes are high. Liza keeps it real, sharing her thoughts on embracing fame (without a personal team to back her up) and why early support from viewers can completely change an artist’s trajectory 🎥🍿 Jared doubles down, explaining why it’s so crucial to hit play early and often with the artist you support. Also share content!

Things get hilariously chaotic as they swap stories about handmade party bracelets and spicy food disasters à la Hot Ones. They break down the delicate art of being a good plus-one and navigating awkward guests at comedy events. Liza’s take? Comedians are just sensitive souls who really want people to “act right” 🙃.

The conversation takes thoughtful turns too, as they reflect on how jokes hit differently based on lived experiences, outdated ideas of bravery in entertainment, and the importance of keeping passion at the heart of the craft. With witty banter, deep insights, and plenty of laughs, this episode is a must-listen. And seriously — hit play on Night Owl now! 🎤✨

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Factor Support the show and get 50% off your first Factor box, plus free shipping. Use the code JTRAIN50OFF at https://www.factormeals.com/JTRAIN50OFF

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

This week on the JTrain Podcast, Jared kicks things off with his thoughts on Sunday football, as the Chiefs and Patriots gear up for the Super Bowl. Then, it’s time for Ticked Off Tuesday, where listeners air their grievances, and Jared adds his signature hilarious commentary.

Topics include:

• A belated Christmas delivery that brought two giant boxes of cinnamon buns and baklava, completely derailing office diets and macro goals. The calorie counts? Nightmare fuel.
• A pedicure disaster involving new massage chair “technology” that smashes thighs and sends “butt rollers” into action—with confusing controls labeled “Air Mode.” Who signed off on this madness?
• The frustration of one-star reviews complaining about shipping times instead of the actual product. If you’re rating the mailman, do it somewhere else!
• A gym TV debacle: 10 screens filled with depressing news instead of lighthearted shows or sports. Isn’t the gym supposed to be a de-stress zone?

From carbs to cardio and everything in between, Jared breaks it all down with humor, logic, and just the right amount of outrage. Tune in for relatable rants and laugh-out-loud moments!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Nutrafol Support the show and get $10 off your first month’s subscription of Nutrafol, plus free shipping. Use promo code FEATHER at https://www.nutrafol.com

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

Instagram - https://www.instagram.com/venetiaageras/

Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

--

Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/

In this week’s Mailbag Mondays, host Jared dives into two emotionally charged listener dilemmas that demand his signature blend of humor and honesty. From virtual betrayals to mixed signals in the workplace, Jared is here to break it all down.

First up, a listener grapples with the aftermath of discovering her husband’s emotional affair in the virtual reality world. After learning about the betrayal—complete with screen grabs and “I love you” messages—she’s left questioning everything about their marriage. Jared shares thoughtful advice on rebuilding trust, navigating marriage counseling, and figuring out how to stop the obsessive cycle of re-checking and replaying. Can their relationship survive this digital heartache?

Then, it’s a tale of workplace flirtation gone cold. A listener met a guy at her job just as he was leaving, took a bold shot in his DMs, and got... an ambiguous response. Is she reading too much into it? Should she shoot her shot one more time or let it go? Jared dissects the psychology of social media follow-backs, modern dating ambiguity, and why some guys just can’t commit to grabbing a drink.

Whether it’s navigating marriage post-betrayal or decoding the maddening mind games of dating apps, this episode is packed with Jared’s no-nonsense advice for anyone trying to make sense of modern love. Don’t miss it!

Want more JTRAIN? Join the Patreon for more, listen to Coffee with JTrain, & send an email to 👉[email protected]

Support the podcast by supporting our sponsors!

Nutrafol Support the show and get $10 off your first month’s subscription of Nutrafol, plus free shipping. Use promo code FEATHER at https://www.nutrafol.com

🙋🏻‍♂️ Jared Freid

Instagram - https://www.instagram.com/jaredfreid

Twitter - https://twitter.com/jtrain56

TikTok - https://www.tiktok.com/@wizardofha

Website - https://jaredfreid.com/

🎙🚊Follow JTrain Podcast

Patreon - https://www.patreon.com/jaredfreid

Instagram - https://www.instagram.com/jtrainpodcast

🙋‍♀️ Our Producer Venetia AKA V

Website - https://www.venetiageras.com/

Twitter - https://twitter.com/venetiaageras

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Hop on the "JTrain" with comedian Jared Freid and his crew of pals, including YOU! Join us for an hour of laughs, gripes, and straight talk on modern love. Send in your questions, dish on the latest trends, and more to [email protected] – we'll tackle it all on air! It's a no-nonsense, fun journey where we escape reality for a bit, delivering quick laughs and razor-sharp insights into the wild world of life and love. Tune in every Monday.

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Jared Freid is a stand up comedian from Boston and who is currently based in New York City. Jared is known to give great dating advice and is all knowing of the Bachelor & Bachelorette nation! You can catch his latest comedy special on Netflix, “37 & Single”, where Jared discusses dating app frustrations to awkward setups to breakup justifications. (For the record, Jared’s mom thinks his body is “just fine.”) Besides regularly headlining and touring around the country, Jared hosts two podcasts called “The JTrain Podcast” and “U Up? Podcast” with Jordana Abraham of Betches, where they discuss their takes on modern dating with issues ranging from apps to hookups to relationships. Check out more of his comedy and a live show today! 👉https://jaredfreid.com/