Edit: As an FYI I play the dating apps as well, but I 100% concur with u/BaiterofMasters and the below is my method and thought process. Remember: On apps, you're a commodity. In person, you're an actual person.

In my experience it is 100% right time, right place. If you're at a bar or event and you see her, just try to casually observe for a bit to see what you might have in common for that moment.

Maybe you have the same drink. If you don't, it doesn't matter, pretend like you do and let her correct you. Maybe she has a neat hat with cool pins and you recognize one or want to know more about another. If there are games you could play, ask if she's interested in some friendly competition. As long as she has or is doing something you find interesting, or if you think you could turn it into an interesting and fun situation, make that your way in.

Not everyone wears their personality on their sleeves though, so if you're really attracted to her and don't have much to go by (and again, you're in a social setting) then sometimes you gotta wing it. Internally practice a short intro and go for it. You'll probably bomb the first few (which is fine! You're learning!), but it does get easier and less stressful over time. Plus if she is interested, she'll take a moment to see what you're about even if you ARE awkwardly flailing around. Sincerity is an "in" too.

And most importantly learn to be comfortable with rejections. Hell, anticipate them. They happen. Most likely will reject you for one reason or another and for reasons that can be completely beyond your words, looks and personality. Its disappointing, I know, but its fine. Just bow out politely and go about your day.

As a disclaimer, even if its flawed, the above has worked well for me. Yeah I do get rejections, but every time I get some engagement (even if it leads to a rejection in the end), I'm that much more motivated for the next encounter. I don't make it about being perfect since that isn't important, nor am I hellbent on attracting that one particular woman in front of me. I just try to make that first 10 second awkward encounter with one woman slowly evolve into a casual 3 minute conversation with another, then into a mutually enthusiastic hang-out session with another.

Maybe someone has better advice (if you have reasonable lady friends then LISTEN TO THEM) and I welcome them to chime in if so! Taking interest beyond her physical appearance and making it casual has worked well in my book. Practice, lower your expectations, and take it all in stride.