U Up? - Is the Pen Pal Dating Trend Back?

Date: October 17, 2025
Hosts: Jordana Abraham & Jared Freid

Episode Overview

In this lively Friday Feels episode, Jordana and Jared dissect the resurgence of the "pen pal" dating trend—where people end up texting endlessly without making concrete plans to meet. Spurred by a viral TikTok from Bethenny Frankel, the hosts explore why this behavior is common, who benefits from it, and share their personal takes and advice for listeners stuck in digital limbo. The episode also features their popular "Petty or Prudent" segment on post-breakup etiquette and a discussion about navigating friendships with significant age gaps.

Key Discussion Points & Insights

1. The 'Pen Pal' Dating Dilemma

Starts ~01:18

• Bethenny Frankel's Viral Question ([04:10])
  Bethenny Frankel shares her confusion about men who only want to text rather than make real-life plans:

  "So you'll go out with someone one time, like each other... Sometimes it's so far between the first plan and the next plan that you forgot about them. One person said to me, 'Oh, what are your plans in November?' I'm like, I'll be dead in November. What are you talking about?"
  (Bethenny Frankel, 04:10)

• Jared’s Perspective on Bethenny and the Trend
  Jared expresses frustration at the ongoing confusion around the pen pal problem, especially from accomplished women:

  "We've answered this for seven years... These men are not stupid. They know what they're doing."
  (Jared Freid, 01:31)
  He reflects on how TikTok both helps and hinders public figures like Bethenny, sparking endless conversations on repeat topics.

2. Why Is 'Pen Pal Season' Back?

Starts ~07:04

• Seasonal Factors
  Jared explains that fall brings fewer excuses for not meeting up, causing more people to get stuck in texting limbo:

  "You know why it's pen pal season? Because it's fall. There's less excuses [not to meet]."
  (Jared Freid, 07:05)

• Gendered Socialization and Scarcity Mindset
  Jared reflects on male behavior rooted in societal expectations:

  "When you get someone who will talk to you—a woman that will talk to you—you hold on to her like she's an acorn that you might need when it starts snowing."
  (Jared Freid, 08:08)

• False Intimacy & Misaligned Expectations
  Jordana describes the disconnect:

  "Men will text you like you're your boyfriend and you've been on one date. And there is this false sense of intimacy..."
  (Jordana Abraham, 08:38)

3. Spectrum of Reasons for Pen Pal Behavior

Starts ~09:51

• Why Do Some Men Pen Pal?

  • They like having options and the ego boost of an interested person
  • They’re lonely and want attention
  • They’re transitioning out of another relationship and keeping backups
  • They have no real intention to meet, just enjoy the flirt
  • Sometimes, they're genuinely busy, but this is rare

  "There's a number of reasons a guy pen pals. One: they really like getting a text from someone. They're lonely and you're just someone."
  (Jared Freid, 09:51)

• Key Quote:

  "Men love vague options. So they text and text and text all..."
  (Jared Freid, 10:42)

4. How to Respond to Pen Pal Behavior

Starts ~12:46

• Jordana Asks for Advice:
  What should you do if a guy is texting but the next date is vague or weeks away?

  "How do you recommend I deal with you [if you're pen palling]?"
  (Jordana Abraham, 12:46)

• Jared’s Advice:

  • Be clear and prompt: "Hey, I'm game for next week. Just make a plan and I'm in."
  • If met with vagueness, respond with light-hearted acknowledgment, then pivot: "Well, when you're ready, shoot me a text for a plan and we'll see if I'm free."
  • If you're uninterested, simply stop engaging: "I just wouldn't even answer." (Jared Freid, 15:17)

• Honesty and Boundaries:
  Jordana emphasizes her position:

  "I relate much more to [Bethenny] where I'm like, I don't really care about you visiting your niece this weekend. Like, I don't really know you."
  (Jordana Abraham, 16:39)

  Jared counters that he doesn't mind ongoing texts, showing how perspectives can differ even among daters.

5. Mixed Signals and ‘Relationship’ Definitions

Starts ~18:10

• When Does Pen Pal Behavior Become a Problem?
  The hosts discuss how confusing it can be when texting suggests connection, but real momentum isn't there:

  "I do think it's like... tough when you're like, I actually do want to see this person for a second date. I want to keep talking to them, but I don't want to keep talking to them in a way that feels like it's going nowhere."
  (Jordana Abraham, 18:10)

• Key Insight:
  The difference between someone looking for real progression and someone just enjoying casual attention is often the root of pen pal frustration.

6. Petty or Prudent: The Post-Breakup Survivor Pool

Starts ~27:10

• Listener Email: What do you do if your ex remains in your friend-group’s NFL Survivor Pool after a breakup?
  Should he forfeit, or is continuing okay?

• Jared and Jordana’s Take:

  • If participation is passive/on an online platform with no direct group chat interaction, it’s prudent for him to stay in.

  • If he’s actively engaging with her friends or in a chat, it might get petty.

  • They stress communication and emotional honesty:

    "Every time I see you make a pick in this group, it really makes it hard to move [on]..."
    (Jared Freid, 29:31)

  • Both agree breakups don’t mean someone vanishes from all mutual circles—but sensitivity is key.

7. Older vs. Younger Friendships: Creepy, or Normal?

Starts ~38:52

• Listener Email: Is it creepy for a man in his 50s to ask a woman in her 30s (former colleagues) to lunch?

• Jared and Jordana’s Response:

  • As long as the invitation is respectful and no pressure is applied, this is not creepy.
  • The age gap might unsettle some, but both are adults.
  • Key distinction: “creepy” is often just unwanted attention—the behavior isn’t inherently inappropriate.
  • Quote:

    "He asked her to lunch, which is like the most uncreepy... It's not like he was sending her dick pics."
    (Jared Freid, 40:22)

Notable Quotes & Memorable Moments

• On pen pals and mixed messages:

  "I'm not texting guys that I don't want to date. That's why... I wouldn't just be texting a guy unprompted... if I didn't want to date him."
  (Jordana Abraham, 19:30)

• On men’s intentions:

  "Your version of 'not want to date' is not my version... I would text someone who I enjoy their company, I think is hot, and it's fun. There's no end game here."
  (Jared Freid, 19:45)

• On boundaries and clarity:

  "If you hate it, you're not confused. You're turned off."
  (Jared Freid, 12:08)

• On false intimacy:

  "There is this false sense of intimacy it feels like they're bringing, where—I'm sure there's been many women who think they're dating you and they haven't been on that many dates..."
  (Jordana Abraham, 08:38)

Timestamps for Important Segments

• [01:18] – Main theme introduction; reaction to Bethenny Frankel’s TikTok
• [04:10] – Bethenny Frankel's full “pen pal” video
• [07:04] – Why 'pen pal' season comes back every fall
• [09:51] – Jared lists reasons men might be "pen pals"
• [12:46] – Advice on dealing with the pen pal dynamic
• [15:17] – Strategies for disengaging or clarifying intentions
• [18:10] – Mixed signals and their emotional toll
• [27:10] – "Petty or Prudent": Breakup sports pool drama
• [38:52] – Email: Navigating friendships/relationships with significant age gaps

Conclusion

Jordana and Jared offer a nuanced, practical—often humorous—take on modern dating frustrations. They emphasize being honest with yourself and others about your intentions and boundaries, the importance of clear communication, and recognizing that sometimes, “pen pal” dynamics say more about what someone wants from you (or doesn’t) than what they’re willing to come out and articulate. Listeners are encouraged to decide what feels right for them, cut off energy drains unapologetically, and not overthink perceived “confusion” when usually, the answer is pretty clear.

Main Takeaway:
Be clear about what you want in dating, don't be afraid to set boundaries, and stop giving pen pals more emotional energy than they're willing to invest back. And never confuse respectful interest from someone older for "creepy" unless there's actual discomfort or inappropriateness involved.