I honestly have ZERO experience so take this with a grain of salt: most guys avoid the apps as well as street girls because of the risk. The pickup part is easy from what I hear. You don't need to go out for dinner. Many are working and will let you know it.
Just follow the rules here
https://catadorcolombia.com/threads/safety-as-a-solo-traveler.18763/ for your safety. The pickup part is easy. Perhaps if
@SkankHunt42 sees this, he can chime in. He seems like the only one here who consistently uses the apps with success. Or at least the only one who posts about it.