Dear Jackass

Pip: Welcome to Dear Jackass — where the advice is unsolicited, the problems are deeply human, and today someone got a face full of evidence that modern dating is not going well.

Mara: erica1837 is behind the advice desk this episode, and we have one letter that cuts right to it — unsolicited photos, the cowardice behind them, and what a person is actually supposed to do when that happens.

Pip: Let's start with the phallus problem.

False Phallusies

Mara: The question on the table is a simple one with a complicated cultural answer — why do men send unsolicited photos, and what should a person actually do when it happens?

Pip: The setup is almost too perfect: a compliment about a face leads immediately to an escalation, and the response in the column is direct — "I think the real reason men do this is because they are too cowardly to just say what they mean and get to the point. Do you want to get laid because I do."

Mara: That's the real diagnosis here. It's not confidence — it's a workaround. The photo is a test balloon because asking directly feels too exposed, so instead the risk gets offloaded onto the recipient.

Pip: And the recipient, for the record, did not ask to be a test site.

Mara: The column offers several counter-moves. Ask him if he thinks it's handsome. Send back something equally unwarranted. Or — and this one is genuinely tactical — tell him it's cute, that you miss yours, and that you sometimes regret having it removed. The column's word for what follows is "crickets."

Pip: That is a scorched-earth solution and I respect it completely.

Mara: There's also a structural note worth taking seriously. The column points out the letter writer could have ended the text conversation at any point — it was in text. The exit was always available.

Mara: The column closes with advice that is, on its surface, absurd and, on reflection, not wrong at all — get a dog, or find a woman who has one, probably drives a Subaru, and shares the pet with an ex.

Pip: Honestly, as a lifestyle prescription, that holds up.

Mara: The throughline is that the behavior isn't mysterious — it's just low-stakes gambling with someone else's comfort. The column names it plainly and the counter-strategies follow from that naming.

Pip: Which raises the larger question of what we expect from people when the barrier to bad behavior is basically nothing.

Mara: Dating, cowardice, and tactical exits — all in one letter.

Pip: Same time next week, when the Jackass desk presumably has more mail, because it always does.