Catherine Reitman on How to Be Funny Over Text

Being funny over text is a different skill than being funny in person, because you lose your face and your voice and you're left with just words on a screen. Catherine is a useful example here because she names a sense of humor as something she values directly, which means she's not just open to a joke landing well — she's actively hoping for one.

Read what she actually asked for

Catherine writes that she values sincerity, a sense of humor, and engaging conversation. That's practically a checklist. It tells you she doesn't want jokes that feel like a performance, and she doesn't want irony that hides what you actually mean. The funniest thing you can do with someone like Catherine is be sincerely funny — say the true thing in a way that's a little unexpected, rather than reaching for a line that sounds clever but says nothing about you.

Let the timing do the work

Humor in chat lives and dies on timing, and unlike in person, you control it completely. You can take a beat before replying. You can let a message sit for a second so the next line lands with more weight. If Catherine mentions finding joy in simple moments, the worst response is a joke that steamrolls right past it. The better move is to let her sentence breathe, then respond with something light that shows you actually read it — not just skimmed for a setup.

Build on what she gives you, don't perform at her

Catherine mentions loving to learn new things and spending time with people she cares about. Those two lines are an invitation, not a punchline waiting to happen. Funny chat usually comes from noticing a small, real contrast — the gap between "learning new things" sounding productive and how often that new thing turns out to be something completely useless. You don't need a rehearsed joke. You need to notice the gap and say it plainly. That's closer to what she means by sincerity and humor together than any one-liner would be.

Keep the joke short and let her answer

A long joke in text reads like a monologue, and monologues don't leave room for a reply. Catherine is here for engaging conversation, which means the goal isn't to make her laugh once and stall — it's to hand the conversation back to her with something she can build on. One short funny observation, then a genuine question, works better than three sentences trying to land a single laugh.

• Say the true thing in an unexpected way, don't perform an unrelated bit
• Wait a beat before replying so timing feels natural, not rushed
• Respond to what she actually wrote, not a generic setup
• Keep it short enough that she can jump back in
• End with a question, not a mic drop

Being funny with Catherine isn't about clever lines — it's about noticing what she actually shares and responding with warmth, timing, and something true.