About this site.

questionstoaskyourcrush.com is a small editorial reference for the conversations that happen before a first date. It is hand-edited, ad-free, and built around a single discipline: curation, not volume. The web shows twenty-five to thirty carefully chosen prompts per moment; the eventual cluster app holds the longer paced sequences. This site is the public-facing version of the same library.

The editorial position

The dominant pattern in search results for crush questions is the two-hundred-and-sixty-prompt padded SEO listicle, organised by Pinterest categories (juicy, freaky, twenty-one questions). The prompts inside those lists are widely recycled, and the recipient has heard most of them before. This site is built explicitly to be the opposite: fewer prompts, more carefully chosen, organised by the moment of contact rather than by category.

The crush SERP is the most successfully poisoned of any in the four-site cluster by exactly that listicle pattern. The discipline matters most here. The editorial team have deliberately not built /21-questions, /juicy-questions, or /freaky-questions pages even though the SEO temptation is strongest in this category. The questions not to ask page is the public statement of which prompts have been skipped and why.

What this site is not

Not a substitute for therapy. Some of the conversations these prompts touch are genuinely heavy. A licensed therapist beats any list of questions on the internet for serious questions.
Not affiliated with any dating app. The site is independent. No dating-app pays for placement. No app is recommended as “best”.
Not a pickup-artist tool. The prompts are curiosity practice. They are not engineered for conversion. Using them as conversion tactics defeats their purpose.
Not an authority on your specific crush. The prompts are general; the people are specific. Any list of questions is a starting point, not a procedure.

The app, when it ships

A cluster app is in development. It holds two hundred more prompts per moment, plus shuffle, save, and ladder mode (a ten-prompt sequence paced over ten conversations). Ladder mode is the single feature this site converts toward; it walks the reader from light to deeper across a real text thread, with timing prompts. The app stack is React Native with Expo, RevenueCat for subscriptions, Supabase for backend. Pricing is in draft, sub-five dollars a month with a free trial. iOS first, Android fast-follow.

The cluster

This site is one of four in a small editorial cluster. They share the same voice and curation discipline, and they sit on a sequential pre-relationship-to-relationship arc:

questionstoaskonadate.com is the natural forward step after asking-them-out: on-the-date prompts for the first ten minutes, the mid-meal pause, walking and talking, the after-the-date thread.
questionstoaskyourboyfriend.com picks up once the relationship is established: first three months, becoming exclusive, year one anniversary, after a fight.
questionstoaskyourgirlfriend.com is the parallel site to the boyfriend one, same arc, different voice register.

The four sites form a sequential reference. A reader who lands on this site via Google and later finds the date site (or the eventual app) feels the same writer's hand.

Disclaimer, restated

This site is independent and not affiliated with any dating app or coaching service. Prompts are written by humans who remember what it was like to have a crush, not by clinicians or pickup-artists. If you are navigating something serious, a licensed therapist beats any list of questions on the internet.

A Digital Signet editorial site. Last verified April 2026.