Shane Mac, CEO and co founder of the conversational AI company Assist, had a problem. After spending most of his time and energy on keeping his young company running and funded, dealing with the semi rote work of writing to strangers on dating sites was more of a time sink and emotional drain than he liked. So—following the law of the instrument—he created a bot to automate the task. Mac is only one of many dating app users—so far, apparently all men—that the idea has occurred to. I first came...

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