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Your price point is definitely too low. I'd test higher than 9.95 as well (and higher priced multi month).
The gay market is impossible to convert on dating thanks to grindr etc... Like suggested above I'd be more aggressive with email and upsells, and the coreg isn't a bad idea.
Do you have a traffic source that isn't cards at bathhouses? Honestly $50/day is not bad with where you're at.
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