Do I Shoot My Shot With My Optometrist?!? - MONDAY MAILBAG
The JTrain Podcast
Jared Freid
4.8 • 4.8K Ratings
🗓️ 29 December 2025
⏱️ 33 minutes
🧾️ Download transcript
Summary
Mailbag Monday lands in the weird, snack-filled limbo between Christmas and New Year’s, and Jared proudly reminds you that while other podcasts are “resting,” Uncle J Train is still clocking in. He tackles a Hallmark-level dilemma about crushing on a cute, ring-free optometrist and how to shoot your shot without turning it into a LinkedIn crime scene. Then he breaks down the “fifth date shut down” question and why silence afterward can actually be a helpful answer for both people. The episode takes a surprisingly sweet turn with a one-year-later follow-up from a listener who finally said “I love you” after a divorce—and it worked—sending Jared into full sentimental mode. It’s equal parts dating advice, gentle pep talk, and holiday-season camaraderie.
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Transcript
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| 0:00.0 | It's a mailbag munder. |
| 0:03.3 | You've got problems there. |
| 0:07.3 | I'm going to help you from the comfort of my chair. |
| 0:12.4 | It's a mailbag Monday. |
| 0:24.2 | Hello and welcome to the J-Train podcast. |
| 0:29.0 | This is J-Train Jared Freed coming alive from Delray Beach, Florida. |
| 0:30.0 | That's right. |
| 0:41.6 | Every Monday is a mailbag Monday where me, the comedian, takes you, the listeners, emails, and we answer them. |
| 0:48.7 | You might be new here because this is the week between Christmas and New Year's. Yes, we've entered into the timeless abyss where calories do not count and work does not get done, |
| 0:58.3 | but time somehow stands still. |
| 1:02.6 | And for some reason, your podcasts have taken a week off. |
| 1:09.3 | Your friend, supposedly, was like, ah, good luck during the week |
| 1:17.1 | where you needed the most, not your Papa JT, not your dear old Uncle J train. I'm here every day |
| 1:25.5 | for you to put your brain on the shelf. Let me take the wheel. You got to walk? I'm here every day for you to put your brain on the shelf. |
| 1:28.3 | Let me take the wheel. |
| 1:30.3 | You got to walk. |
| 1:31.3 | I'm going to be there with you. |
| 1:32.6 | You got to drive. |
| 1:33.5 | I'm going to be there with you. |
| 1:35.6 | I ain't leaving your side. |
| 1:37.5 | What do I ask in exchange for this? |
| 1:40.4 | Tell a friend, a coworker, a brother, a sister, a mama, a papa, anyone who might need that in their life as well. |
... |
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