Practice practice practice. You just have to get comfortable with yourself. Have the ability to see humor in the moment and express it. To laugh at yourself.
Do you need to do some work on yourself, absolutely. You don't need a gym bod, but be healthy. Teeth, dress are important. Fingernails, shoes, get noticed.
Places to do it. Common interest you can strike up conversations. And in social atmospheres. Learn to dance.
Approach on the street you are a creep, approach at a Salsa street festival starting with eye contact, a smile, an offered twirl, taking the lead, not taking overt liberties, that works.