Advice from the old lady:
Here’s how you get good at approaching. Period. You get good at conversation with random strangers. Here is the brilliant thing, you can practice on literally anybody. Men, old ladies, store clerks, people next to you in line at the store. Start conversations with strangers. What do you talk about? Something of interest to the OTHER person. Pay attention to what they are driving if you’re at the gas pump (how do you like that car….), what they are buying (what’s a good way to make pork chops….), the locale (you know any cool live music spots around here…), the activity (how’d you get into skiing…..)
The other thing is you have to get out of the house. Right now I’m skiing. My fiancé stayed in this afternoon & I wanted to get more runs in…off I go by myself. Ski lifts are wonderful places to chat with your neighbors, so are golf foursomes, so are drag races or baseball game concession lines (any league), at a coffee shop ask the chick next to you what’s good….the possibilities are literally endless.
Learn to chat with people; learn to be curious about and interested in other people. Quit worrying about what people think of you (you aren’t that important, nobody cares so it doesn’t matter what anybody thinks.).
The better you get at chatting to random people, the more it will help you chat with women you like.
Last I checked women are people too. All a woman you see & get curious about is? A female random stranger. Just be more observant than commenting on her looks. Her looks are too obvious. Ask her why she picked that menu item, that bottle of wine, how she likes this ski resort, you get the idea.
Nobody is going to bite you, and if you get a weird reaction? Shrug it off, humor it off, wash rinse repeat. Attach ZERO care to someone else’s reaction. Good, bad or indifferent, but learn as you practice.
Some of y’all need more practice with basic conversation.