The Bert Show — Vault: Is She About To Make A Mistake With The Guy She's Dating?

Air Date: January 8, 2026
Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, et al.)

Episode Overview

In this episode, The Bert Show team catches up with Dana, a 27-year-old woman who, after never having dated before, has become involved in a serious relationship with Matlock—a 58-year-old friend of her parents. The hosts and listeners weigh in on Dana's rapid romance, exploring concerns about age differences, the nature of first love, skepticism from friends and family, and whether Dana is making the right decision as her relationship accelerates.

Key Discussion Points & Insights

1. Dana’s Unusual First Relationship

• Dana, 27, had never been on a date before meeting Matlock (58), who is a friend of her parents.
• She describes being "so in love" and spending time with him nightly. The relationship quickly became serious—including talks of moving in, plans for a vacation, and the gift of a promise ring.
  • Quote (Dana, 02:23):
    "Honestly, I really didn't think I would be where I am right now. Just from one date... I'm so in love with him."

2. The Relationship’s Rapid Progression

• Vacation to the Bahamas already planned over Memorial Day.
• Promise ring given by Matlock and discussions about moving in together as her lease ends in June.
  • Quote (Dana, 04:15):
    "Everything is so great... He's even given me a promise ring, which is just incredible."
• Dana's parents remain skeptical and believe the relationship may be a "phase" (05:33).

3. Intimacy and Daily Life

• Dana recounts being at Matlock's home every night and states the intimacy is “great” (03:32).
• She insists the relationship is mutually caring and not one-sided in decision-making.
  • Quote (Dana, 07:22):
    "...when it comes to making decisions, I put my two cents worth in... I don't feel like I'm being led in any direction by him."

4. Skepticism from Friends and Hosts

• Dana’s friends are divided between supporting her happiness and cautioning her about heartbreak (08:25).
• The hosts debate whether the central issue is the age gap or the fact that it's Dana's first relationship.
  • Quote (Host B, 06:38):
    "I feel like if it was two 27-year-olds... that's just them being infatuated and not thinking clearly. But... I just feel like he's taking advantage of her naivety."
• Concerns are raised about potential power imbalances and whether Dana is trading naivety for security.

5. Financial & Domestic Concerns

• Listeners (e.g., Terry, 10:10) call in to speculate Dana may be after Matlock's money, but she refutes being a “gold digger,” mentioning her job as a clothing buyer and her financial independence (10:29).
• Hosts raise questions about whether moving in means she’ll become a caretaker (09:15), but Dana asserts Matlock is self-sufficient.

6. Promise Ring Controversy

• Promise rings become a source of lighthearted debate.
  • Quote (Host B, 11:36):
    “I think promise rings are full of crap.”
  • Quote (Host C, 11:47):
    “It's a promise. It's what you give when you're not [old] enough to get engaged.”
• The cast jokes about the appropriateness and meaning of a promise ring given by a 58-year-old.

7. Listener Perspectives

• Some listeners phone in, expressing both support and skepticism.
  • Quote (Caller, 11:01):
    "I just wanted to say that I support her and... when you find love, I think you should hold on to it."

Notable Quotes & Memorable Moments

• Dana on falling in love:
  “I just feel like... I definitely have an amazing thing here.” (02:55)
• Host B on skepticism:
  “Are you sure he doesn't... need somebody to take care of him?... I'm just wondering if the roles are going to change a little bit once you get in there.” (08:45)
• Dana on domestic roles:
  “He actually makes things for me and I make things for him... everything else he does himself.” (09:38)
• Promise ring skepticism:
  Host B: “I think promise rings are full of crap.” (11:36)
  Host C: “Promise rings are okay if you're 16.” (11:40)

Timestamps for Important Segments

• [01:41] — Start of Dana's story recap
• [02:23] — Dana’s reflections on her new relationship
• [03:32] — Discussion of intimacy
• [04:15] — News of promise ring and moving-in talk
• [05:57] — Discussion of parents’ reaction
• [06:35] — Hosts debate issues: age or lack of dating experience?
• [08:45] — Host raises concerns about power dynamic and caretaking
• [10:10] — Listener accuses Dana of being after money; Dana responds
• [11:36] — Promise ring debate

Tone and Final Thoughts

The episode is playful yet probing, blending concern with lighthearted teasing. The cast routinely challenges Dana, but she remains insistent about her agency and happiness. Listeners and hosts alike are sharply divided—some warning of heartbreak and manipulation, others rooting for unconventional love.

To Be Continued: The Bert Show promises a follow-up with Dana in two weeks to see if things have changed as her relationship and vacation plans move ahead.