1. He’s out with the commercial sign spinners, but he’s just advertising himself.

    I think the “or both” is a secondary joke, but it’s odd enough to catch your brain. My main problem with it is that “both” seems to imply hiring him as a gigolo.

  2. Having a math background, the tickler in the joke is making the distinction for Xor (exclusive or [A or B but not (A and B)] as compared to Or [A or B or (A and B)]

    Doug is flexible, he’s cool with both options. For me, I’m guessing that Doug is also ok if each option is from a different person. Doug is just that kind of guy.

  3. Doug is self-employed as a sign-spinner. And as a dating app. (Neither of which make much sense.)

    He’s also self-employed as one of those guys who leaves reviews.

    What a catch!

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