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DATING advice from JAMES CAANπŸ˜‚πŸ’πŸΏ #flyonthewall #shorts #comedy

June 12, 2026 / 01:00

This episode features discussions about Jimmy Caan's advice on acting and dating, particularly a humorous anecdote involving a first date. The conversation touches on the unconventional advice Caan gave, which included a suggestion to relieve oneself before a date.

The hosts share laughter as they recount this advice, with one host mentioning a comedian who followed a similar practice before dates. The lighthearted banter continues as they joke about the advice being applicable in different contexts.

As the conversation progresses, the hosts transition to discussing clips related to the topic, maintaining a playful tone throughout.

TLDR

Jimmy Caan's humorous dating advice sparks laughter and anecdotes among the hosts.

Episode

1:00
00:00:00
Tell us about Jimmy Caan, >> Yeah. >> please. >> He you know, gave me some really
00:00:03
interesting advice back in the day. Not only about acting, but also about dating. I don't know if we can share
00:00:08
that here, but >> We're kind of a dating show. >> I had a date. I'm not going to say who
00:00:12
it was with, but I had my first date and >> Madonna? >> You know. >> [laughter]
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>> And I said, "Jimmy, what do I do?" He says, "Well, jerk off before you go on the date."
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>> Excuse me? >> Masterbate. I have heard this theory. Before I went on the date so I didn't
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have any sort of >> I knew a comedian who would do that. >> Before you go on stage?
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>> [laughter] >> No, before he go on a date after the show. >> I never practiced it because
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>> Except before podcast, right? >> Well, that's different cuz that's
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business. >> [laughter] >> That was his sage advice for me on my first date.
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>> And did you follow it or no? >> Probably. >> All right, let's look at a clip.
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>> [laughter] >> Always go to the clip. I couldn't wait to say it that time. He was He's been
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holding that go to the clip thing for like 2 minutes. He knew He waited for the opening.
00:00:58
>> Yeah.

Badges

This episode stands out for the following:

  • 70
    Funniest
  • 65
    Most unserious (in a good way)
  • 60
    Most memeable

Episode Highlights

  • Jimmy Caan's Dating Advice
    Jimmy Caan advised to 'jerk off' before dates to ease nerves.
    β€œ"Well, jerk off before you go on the date."”
    @ 00m 20s
    June 12, 2026

Episode Quotes

  • "Well, jerk off before you go on the date.".
    DATING advice from JAMES CAANπŸ˜‚πŸ’πŸΏ #flyonthewall #shorts #comedy
  • "That was his sage advice for me on my first date.".
    DATING advice from JAMES CAANπŸ˜‚πŸ’πŸΏ #flyonthewall #shorts #comedy

Key Moments

  • First Date00:10
  • Laughter00:17
  • Dating Advice00:20
  • Clip Time00:49