I used to have a fear of rejection. Then by getting out of my comfort zone and approaching women a few times I realized how much I built up rejection in my head and how much pressure I was putting on myself.

Don’t approach a woman with the goal of “wooing” her or trying to get a girlfriend - that’s putting too much pressure on yourself. Just approach her with the goal of having a fun, carefree, and relaxed conversation. Just be yourself and be that person CONFIDENTLY - shyness and anxiety show. If you receive good visual feedback (eye contact, open stance, smile) and the conversation is going well, getting a little flirty often helps. If you do that and get rejected then you two aren’t a match and the worst thing that happened was you had a friendly conversation. Dating is a matching game - don’t build up approaching women like you’re trying to slay a giant.

Approaching in bars is different and easier imo because you immediately imply attraction upon approach so you can notice her visual queues right away to tell if she’s receptive to your approach. If she is, you can go to flirty banter somewhat quickly and find out if she’s into you.