Podcast Summary: "Dating Apps Are Completely Broken Now" | Not Today, Pal with Jamie-Lynn Sigler and Robert Iler
YMH Studios | November 20, 2025

Episode Overview

This episode of Not Today, Pal delves into dating in the digital landscape, focusing on the pair’s real-life gripes and misadventures with dating apps and relationships. As former Sopranos siblings, Jamie-Lynn Sigler and Robert Iler bring their sharply contrasting personalities to honest, funny, and sometimes vulnerable conversations about love, filtered expectations, dating disasters, and searching for common ground in the chaos of the modern romance arena.

Major Discussion Points

1. Vacations, Homebody Tendencies, and Social Pressures

• Jamie and Robyn discuss their recent travels (Jamie’s acting trip to New York, Robyn’s family vacation in Mexico), their mutual “homebody” personalities, and how this relates to their relationship expectations.
• Highlight:
  • Jamie shares, “I never need to leave a house.”
    • [04:00]
  • Both hosts bond over discomfort with people who need constant adventure during trips, revealing that this attitude extends into their dating lives.

2. Dating App Dealbreakers and Filtering Fatigue

• Rob’s frustration with the endless “filters” required when using dating apps is a recurring theme:
  • He finds being a non-drinker and his dog allergy major stumbling blocks.
  • Jamie and Rob discuss how profiles are filled with travel demands, pressuring people who aren’t adventurous.
• Memorable Quote:
  • “The amount of filtering down I have to do when I’m looking at people to date is so bad. And being very boring is one of the big ones.”
    – Jamie [04:37]
• Rob estimates “eight out of ten” women mention travel as a requirement in their bios. [05:50]
• Rob is upfront about his lack of interest in travel, preferring to stay in and relax—an attitude rarely reflected in dating profiles.

3. Dating App Culture and The “Love Connection” Segment Idea

• Jamie pitches a “Love Connection”-style video matchmaking segment for Rob, but Rob rejects it, fearing he’d come off as mean for critiquing women. Cutter and Robyn chime in that it’d be uncomfortable and potentially hurtful.
  • “I’m not trying to hurt bitches’ feelings.”
    – Cutter [07:13]

4. First Dates: The Gift Card Dilemma

• Rob asks Jamie if a man paying with a gift card on a first date is a red flag.
  • Jamie admits it’d raise her “antennae” a little but isn’t a dealbreaker:
    • “It would plant a tiny seed. It’s not a dealbreaker. But I would be like, okay…”
      – Jamie [10:38]
• Rob and Jamie dissect the awkwardness of using obvious paper printouts or dealing with declined credit cards.
  • Jamie reveals she’s often overlooked financial things if she’s attracted to someone, making her an unreliable “average” for these scenarios:
    • “I’ve overlooked tons of things because I am incredibly attracted to somebody.”
      – Jamie [14:49]
• They share personal anecdotes about financial mishaps early in relationships, including Jamie taking Cutter to an expensive sushi restaurant when he had little money. [17:27]

5. The "I Love You" Timing Debate

• The group discusses how soon into a relationship it feels natural to say “I love you,” revealing a split:
  • Jamie confesses she’s always quick to say it—sometimes within a month.
  • Rob and Cutter are more guarded, often waiting for the other person to say it first.
    • "It's always them first, though. It's like, I'm not gonna say it until you kind of force me to say it."
      – Cutter [22:22]
• They try to script kind, honest responses when someone says “I love you” and the feelings aren't matched. AI and ChatGPT suggestions are read aloud and debated for their merits and coldness:
  • “That is… you might as well kick someone in the head.”
    – Jamie [23:56]
  • “Saying ‘yet’ is like, you’re giving her hope for no reason.”
    – Cutter [24:13]
• Rob notes that because he’s slow to trust, saying “I love you” takes time, sometimes only possible with someone he’s known for years.

6. Personal Stories: Vulnerability, Breakups, and "The Ick"

• Jamie admits she usually initiates breakups when she senses the “ick” and only stayed longer than she should have in one relationship where she wasn’t respected, meeting Cutter a month after that ended. [21:44]
• Both hosts share that awkwardness of mismatched timing for big relationship confessions can be hard to recover from.

7. Hilarious Reactions: Viral Clips, Physical Mishaps, and “Memory Lane”

• The latter part veers into fun, with Rob sharing viral video clips of people spinning uncontrollably on playground rides and amusement parks, sparking laughter and concern over potential “brain damage.”
  • “He’s in another dimension, right?”
    – Jamie [35:59]
• Jamie and Rob reminisce about a 2017 Cable Hall of Fame event, with behind-the-scenes commentary on Jamie’s early pregnancy signs and the nuances of “appointment sex.”

8. Quickfire: Getting Pregnant, Vices, and Relationship Milestones

• Jamie discusses knowing immediately the night she became pregnant.
• They banter about weed versus alcohol use in conception, and cycle back to relationship talk:
  • “We talked about dating, getting pregnant, doggy. We talked about doggy style. Overweight ladies spinning out of control on rides. What else did we cover today?”
    – Jamie [41:47]

Notable Quotes & Memorable Moments

• On modern dating app fatigue:
  • “If you went through a dating app right now, I would say 8 out of 10 girls will mention traveling on their thing. […] I just want to sit, like… and if I were to go somewhere, it would be like, I’m going to sit in the house.”
    – Rob [05:50 - 06:16]
• On first date red flags:
  • “If you have a gift card, like, use it. That’s what I’m saying.”
    – Jamie [10:52]
• On emotional honesty:
  • “I don’t want us to be getting married one day and me know deep down that I said ‘I love you’ when I wasn’t ready.”
    – Rob [31:02]
• On being honest about vulnerability:
  • “I think always putting it on you, be like, ‘I’m fucked up. I’m weird. Like, it takes me a long time.’”
    – Jamie [32:48]
• End-of-episode humor:
  • “You guys keep out there. I think he said something like that, right?” – Jamie attempting a “Love Connection” sign-off [42:15]

Key Timestamps

• 00:41 – Jamie and Robyn catch up on recent life and trips
• 04:37 – Dating “filters” and the trouble with being “boring”
• 05:47 – Dating apps’ obsession with travel
• 06:38 – Love Connection-style matchmaking pitch
• 09:20 – Rob’s disinterest in dating and wishing to “skip to the three month part”
• 10:38 – Gift card on first date discussion; social and psychological cues
• 13:55 – Deeper talk: whose financial “turn” is it in a relationship?
• 17:27 – Jamie’s story: taking Cutter to an expensive sushi dinner when they just started dating
• 21:16 – Saying “I love you” too soon or when not fully felt
• 23:25 – Best and worst ways to respond to “I love you” if the feeling isn’t mutual
• 35:05 – Watching viral videos; physical comedy/reflection segment
• 38:01 – Torch-passing: memory lane and Sopranos event anecdotes
• 39:43 – Conversation about pregnancy “light switch moment”
• 41:47 – Rapid-fire recap of all “important” (and hilarious) episode topics

Tone, Language, and Dynamic

The podcast maintains its hallmark balance of sincere reflection and sharp-edged humor throughout—Jamie’s warmth and Rob’s Oscar-the-Grouch cynicism set against real-life relationship and dating scenarios. Listeners are treated to a rare mix of candid storytelling and playful ribbing, with both hosts openly revealing insecurities and moving quickly between gravitas and laughter.

In Summary:
The episode offers a funny yet honest look at why dating apps feel broken for so many, especially those who don’t fit the adventurous mold; the real awkwardness of first dates; emotional pitfalls of opening up too soon; and why, sometimes, the best relationships are the ones that manage to find humor in life’s messiest moments.