Should I Travel Alone? - MONDAY MAILBAG - The JTrain Podcast w Jared Freid

It's Monday AKA Mailbag Monday 🙌 📩Jared is taking you behind the scenes of the show’s new daily format. Jared explains how he's adjusting his recording schedule to keep pop culture discussions fresh and relevant while also teasing upcoming segments like Ticked Off Tuesday and Chitchat Wednesday with dating expert Logan Ury!

Fresh off a trip from Boca, Jared opens up about his parents' pushy suggestions that he take his dad’s Ozempic—a weight-loss drug—which leads to a deeper reflection on food, body image, and the pressures of success. He candidly shares how trips back home to Florida make him confront personal insecurities about his career, life trajectory, and the tricky dynamics of family expectations. We love the family but sometimes it can be a lot!

He hilariously describes his mom's intense weather concerns and her insistence that his flight would get delayed due to storms. Despite her worries, Jared’s flight went smoothly—until he had an unexpected Uber ride experience. His Uber driver had to urgently stop for a bathroom break, turning a simple ride into a humorous adventure. Jared’s empathy for the driver leads to some great comic moments, from discussing bathroom strategies in NYC to the shared relief they both experience after the driver returns.

Finally, Jared answers listener emails in the Mailbag Monday segment. The first listener, a 34-year-old who has been single for a while, discusses the pros and cons of being alone. Jared reflects on the balance between enjoying alone time and the potential downsides of solitude, offering his humorous yet insightful perspective. This episode is packed with relatable moments, whether it's the stresses of managing life’s expectations, the hilarity of real-life travel experiences, or the deeper reflection on singlehood and personal happiness. Jared responds to a listener wondering if it's time to start traveling solo despite some fear. Jared shares his own experience with solo travel, reflecting on a trip he took to the South of France. He admits that the trip was a bit lonely due to time zone differences and the fact that he was in a vacation town where most people were there with their partners or friends. Jared emphasizes that solo travel can be rewarding, but suggests starting with cities where the language barrier is minimal and where there's more social activity, like New Orleans or Copenhagen. He also recommends shorter trips of around five days to avoid extended periods of loneliness. He even mentions that certain hotels, like the Four Seasons in New Orleans, can provide a more comfortable solo travel experience if budget allows. Ultimately, Jared advises the listener to plan their trips differently depending on whether they’re traveling alone or with someone. He highlights that solo trips can be enriching, but to be mindful of destination and trip length to ensure a fulfilling experience.

Lastly, Jared tackles a listener's dilemma involving a longtime coworker and friend who seems to struggle in dating due to bad breath. While the listener isn't sure how to approach the subject, Jared empathizes with the awkwardness of the situation. He suggests that bringing up the issue gently, perhaps in a moment when the friend is confiding in them about dating frustrations, might be the best approach.

Jared also acknowledges that bad breath can kill affection and attraction, but encourages the listener to remember that if a person is in a meaningful relationship, issues like bad breath can often be addressed without ending things. Jared shares his thoughts on how people in the early stages of dating might use superficial reasons, like bad breath, as a way to back out of something deeper. He closes with some humorous but practical advice on how to approach the delicate subject without damaging the friendship.

Tune in for all this and more, including a shout-out to all of you writing in!