The Bert Show – Vault: All Of Her Exes Are Gay...Why?

Date: January 20, 2026
Host: Pionaire Podcasting Team (Bert, Kristin, Abby, Cassie, Tommy, et al.)
Episode Theme:
This episode centers around a listener, Alyssa, who reveals that both of her serious boyfriends turned out to be gay. The cast and listeners discuss her experiences, why this may have happened, and how it speaks to broader themes of dating, sexuality, and self-discovery, especially in younger years.

Episode Overview

Alyssa, a 21-year-old listener, calls in using a voice disguiser to share her unique relationship history: both of her two major boyfriends later came out as gay. The episode explores her story, the emotional implications, and the perspectives of hosts and other callers who have had similar experiences or insights. Humor and empathy drive the conversation, with a focus on understanding rather than judging.

Key Discussion Points & Insights

1. Alyssa’s Story: Two Boyfriends, Both Came Out as Gay

• Alyssa nervously introduces her situation, noting, “Both guys have ended up being gay.” (00:33)
• First boyfriend: Dated from ages 14-17, described as “a little flamboyant,” but Alyssa was too “naïve” to recognize signs at the time. (00:43)
  • “He could bust a big Beyoncé moment.” – Alyssa (01:53)
  • Came out a year after their breakup.
• Second boyfriend: Met at 18, described as “very manly” and even a bit homophobic as a “cover.” (02:48, 03:46)
  • “He was a guy’s guy.” – Alyssa (03:25)
  • Relationship was serious: lived together, had promise rings. After breakup, he came out and introduced Alyssa to his new boyfriend. (04:25)
  • Both boyfriends admitted to knowing they were gay long before they met her. (04:54)

2. Host Reflections: It's Not Your Fault

• The hosts immediately reassure Alyssa that her experiences are not her fault, emphasizing that many go through similar situations.
  • “There’s no reason for you to be fearful that this will always happen... the older you get, the less you’ll run into this.” – Host (05:23)
• The conversation delves into how societal pressures, especially in youth, can lead closeted gay individuals to seek heterosexual relationships to “try to work it out.” (05:23–06:33)

3. Cheating, Honesty, and Responsibility

• Caller Brad relates, empathizing with Alyssa and questioning if her boyfriends cheated with men during their relationships. (06:45)
  • Hosts express doubt that Alyssa would know, and reinforce fidelity is about honesty, regardless of sexuality. (07:15–07:56)
  • “It’s cheating regardless of who you’re cheating with.” – Host (07:56)
• Another listener, Jennifer, calls sharing that both her ex-husband and a subsequent serious boyfriend later came out as gay. (08:22)

4. The “List” and Attractiveness Factors

• Hosts invite Alyssa to share her list of attributes for an ideal man.
  • Alyssa’s list: “Romantic, willing to have fun, able to settle, watch a movie, cuddle, hold me, a little sensitive, talk to me, carry on a good conversation.” (09:23)
  • The hosts joke, “I would suggest you to continue dating gay men.” (09:57)
• The discussion turns to whether Alyssa’s nurturing personality and openness might make gay men feel “safe” with her. (10:43)
  • “Maybe gay guys are drawn to me because I’m not judgmental... I’m very caring... so they can feel safe with me.” – Alyssa (10:43)

5. Emotional Safety & Attraction

• A host relates her own story of dating men before coming out and feeling more emotionally relaxed because “there wasn’t as much at risk” as there would have been with a woman she was truly attracted to. (11:23–12:29)
  • “Does that make sense?” – Host, checking in with Alyssa (12:29)
• The group suggests that these relationships are often rooted in emotional safety rather than sexual attraction.

6. Moving Forward, Advice for Alyssa

• The hosts assure Alyssa her experience is a “fluke,” not a pattern, highlighting that older, more self-aware partners are more honest.
  • “By the time I was 25, everything was said and done.” – Host (15:54)
• Suggestions range from changing the kind of traits she’s seeking to humorously speculating about “telltale” characteristics (e.g., “collection of Broadway musical CDs” or noticing nail polish colors) as jokes. (16:11–16:30)
• A recurring theme: as people age, “the more secure they are in themselves, the more honest they can be.” (05:23, 15:54)

7. Similar Stories from Listeners

• Amy calls in saying she dated four gay men in high school; again, these relationships were often about providing cover (“beard”) rather than intentional deception. (17:22)
• The show veers into high school band stereotypes as light banter, with the group acknowledging no real “type” can be identified.

Notable Quotes & Memorable Moments

• “He could bust a big Beyoncé moment.”
  — Alyssa, on her first boyfriend. (01:53)

• “He was sort of a typical, stereotypical macho dude.”
  — Host, summarizing Alyssa's second boyfriend. (03:21)

• “He’s a homophobic gay guy.”
  — Host, on the second boyfriend's behavior. (03:46)

• “It’s cheating regardless of who you’re cheating with.”
  — Host, reinforcing the importance of honesty in relationships. (07:56)

• "I would suggest you to continue dating gay men."
  — Host, joking about Alyssa's list of ideal man traits. (09:57)

• "Maybe gay guys are drawn to me because I'm not judgmental... I'm very caring, very nurturing and stuff like that, and so they can feel safe with me."
  — Alyssa reflecting on why this keeps happening. (10:43)

• “By the time I was 25, everything was said and done.”
  — Host, on self-discovery and honesty increasing with age. (15:54)

Key Segment Timestamps

• Alyssa’s introduction and first boyfriend story: 00:33–02:34
• Second boyfriend and the “cover” discussion: 02:48–04:54
• Reactions, broader context (honesty and age): 05:13–07:56
• Caller Jennifer’s similar experience: 08:25–08:40
• Alyssa’s “perfect man” list: 09:23–09:57
• Reasons why gay men might be drawn to Alyssa: 10:43–12:29
• Advice and wrap-up: 13:35–16:16
• More listener stories (Amy dating four gay men): 17:20–18:12

Episode Tone & Language

The conversation flows naturally between empathy and playful banter, with hosts using self-deprecating humor and honest, sometimes raw, reflections about sexuality, adolescence, and relationship confusion. The show prioritizes a nonjudgmental, understanding tone throughout.

Key Takeaways

• Alyssa’s experience, while rare, is shared by others.
• Adolescence is a time of confusion and self-discovery for many, contributing to such scenarios.
• It is not Alyssa’s “fault,” nor does it indicate a pattern that will persist.
• Emotional safety and openness can make some people natural confidantes or partners for those struggling with identity.
• With age comes self-awareness, and such situations become increasingly unlikely.
• The importance of honesty and empathy in all relationships is repeatedly underlined.

For listeners who haven’t heard the episode:
This conversation offers comfort, camaraderie, and practical advice to anyone whose romantic history has involved similar surprises, while providing plenty of laughs and relatable insights along the way.