What to Say to Older Women on Tinder

Say what you would say to any woman you find interesting: one specific, playful line about something she wrote or showed. What changes with an older woman is the register. Matthew and his team of coaches write "woman" where they would write "girl," lean on the sophisticated side of the conversation, and tease her about her character instead of about being cool. A student on one of our live calls asked whether we text a college-age woman differently from an older woman with a career, and the answer was a plain yes.

The simplest adjustment is also the first one: in your own writing, call her a woman, not a girl.

It costs nothing and it sets the tone before you have said anything clever. Everything else on this list is a matter of degree. This one is a switch you can flip tonight.

Matthew's team of coaches describe the split like this. With a younger woman, the conversation leans on fun, and the teasing tends to be about popularity or being cool. With an older woman, it leans on the sophisticated side of who she is, and the teasing is character-based.

Character-based teasing means you pick up on something about who she is, as the profile shows it, and poke at it lightly. A coach gave a clean example for a woman who writes that she reads religiously when nothing else in her profile suggests she is religious. He would tease her about the gap, with a joke that plays on the word, rather than just ask what she is reading.

A second version works on the same idea. If she lists a subject she loves and something about her contradicts it, point out the irony. A coach called that a really good opener for a smart woman, because it proves you read the whole profile and thought about it.

After the tone, Matthew's team of coaches do one last check on every message: is this age-inappropriate?

The example from the call is an original Star Wars reference sent to an 18-year-old. It runs the other way too. Slang that your own friends use can sound off to a woman who is thirty, and a reference that only makes sense to your decade can land flat.

The coach called this a dummy check and said it is the bare minimum. Read the message once as her, ask whether anything in it belongs to a different generation, and cut it if it does.

Men hear "sophisticated" and write like a letter. That backfires.

On the same call, a coach on Matthew's team listed behaviors that read as leveling, meaning they lower your standing in her eyes. Texts that are too complicated do it. So does being too complimentary, pushing for plans in every message, or writing so grammatically that nothing sounds casual. His rule is that being too formal or too try-hard is a big leveling behavior.

There is one allowance. If she is very highly educated, you can get away with being slightly more formal than usual. Slightly. Sophisticated here means your topics and your wit, not your sentence structure.

Age is the last filter, not the first. The coach said he starts with the overall type of woman: artistic, adventurous, nerdy, sweet. Then he proofreads for age.

That is why two women of the same age get different messages. For a smart or nerdy woman, Matthew's team of coaches suggest a few specific moves:

• Ask what the last book she read was.
• Ask what genre of literature she would be.
• Trade favorite quotes: you show yours if she shows hers.
• If she is nerdy about a subject you actually know, make an insider joke or an observation that shows real competence. A coach called that a huge win with the right woman.

All four are specific to her. None of them depends on her age at all.

You are still opening on something in her profile, still keeping it short, and still aiming to move her off the app and onto a date. The coach said he texts an 18-year-old very differently from a 30-year-old. In the same breath he said it is hard to list every adjustment. Each one sits inside everything else he is doing for that particular woman.

So treat the age changes as three small edits on top of a good message: "woman," a sophisticated and character-based tease, and a generational proofread. If the message was generic before the edits, the edits will not save it. If it was specific to her, they will make it sound like it came from a man who is comfortable with her.