Wes Caldwell

Work / Dating product · Los Angeles

Cupid's Day Off

A dating app that matches on how you live, not how you look. Twelve real dating moments build a six-axis profile, and photos stay hidden until both people say yes.

Role
Founder, product, engineering
Status
Live · LA beta
Year
2026
Cupid's Day Off — homepage
12situations in the Gauntlet
6personality axes per person
2 minto your dating type

The problem

Swiping rewards the best selfie. The things that decide whether two people last, like how they split the check, fight or spend a Sunday, never show up on a profile.

What I built

The Gauntlet is a 12-question psychometric test built from real dating moments. Each answer moves you along six axes: Tempo, Rationality, Autonomy, Traditionalism, Expressiveness and Materialism. Matching is distance in that space, batched and reviewed by a human during the beta.

The product runs as a React and Vite front end with an Express API on Supabase, Stripe for payments, and a Docker multi-stage deploy. Security-lockdown migrations and Playwright and Vitest suites cover payments, matching and error handling.

The launch included a modern-noir brand with two recurring characters, The Architect and The Poet, and a scheduled seven-post Instagram launch week.

Stack

React 18TypeScriptViteTailwindFramer MotionExpressSupabaseStripePlaywrightVitestDocker

Integrated Autonomy

Your AI department.

I learn how your business actually runs, find the bottlenecks and build the AI systems that remove them: agents, automations, sites and the infrastructure under them. No packages or templates, and it runs on hardware you own wherever that makes sense.