Depends on a lot of things, most relevant is your age and apperance. Most of the rest you can lie about. Money is a factor to a point. You can pretend to be wealthy but you need a decent amount to afford the illusion.

The next biggest factor is how low your bar is set. If you are willing to fuck sluts it might just be a better strategy to fuck hookers. At least they get tested for STDs.

Realistically if a girl is willing to sleep with you without having a relationship she is doing that with everyone. Why waste your time playing games when you can use one of the many websites to have a hoe come to your door and you know exactly how much it will cost ahead of time. You don't even have to bother with putting up a facade.