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I would love to subscribe to a monthly haircut at a fixed time (something like first Monday of the month at 4pm), use it or lose it.

I’d signup for that

At Silent Barn, there was a barber shop partly run by a great barber (and musician - seems to be a common combo). Our deal was that I paid him $30/month, and he'd take me in twice a month. I always looked pristine and I got a slight deal that turned into a habit, and he had a steady customer.

I feel the exact same way about manicures/pedicures/eyebrow waxing.