Any automated process that depends on human interaction is going to fail, whether it is seeking a job, finding a date.

The big flag here is, after 20 dates, defeat begets defeat. You can't automate success.

Plus, the profile picture sounds a bit like a lie. Anyone who's done online dating is familiar with the angels needed to hide body-type. Of course, no one is going to be happy to see someone who doesn't look like what the photo envisioned.