I'd work on myself in order to make myself attractive to women (go back to school to get a better job, lose weight, lift weights, take up a hobby such as cooking or dancing). I might get a sensual massage or two just to see what female touch is like while doing online dating. Not so sure about seeing a hooker for intercourse. Seems kind of weird to have sex with someone getting paid for it. And with online dating, I'd aim for women that are less popular with men. Like pudgy women or older women. I'd avoid single mothers though.