How to Overcome Fear of Rejection in Dating Women

The real obstacle here is the fear.
As I mentioned, fear of rejection, or imagining rejection when you should be imagining success, leads to walking away.
You miss 100% of the shots you don't take.
Ironically, I've found that the best way to overcome my own fear of rejection was to see that it wasn't going to actually happen.
The more times I approached women and started conversations and the more I saw that women usually responded positively, the less I imagined things going wrong.
This led to a positive feedback loop of me wanting to approach more women and have more success.
Here are a few ideas for overcoming your own fear of rejection:
1) Go out to a bar, and watch men approaching women.
Take a Saturday night, and just go out alone. Find a seat at the bar where things are busy, and just watch.
Make sure you visit a place that is really busy, so you can see a lot of people interacting.
Now, pay attention.
You'll begin to pick out the guys who are approaching a lot of women, asking them to dance, buying them drinks, etc. Watch what happens.
You'll be able to see for yourself that most of the time, even if the woman isn't interested, nothing bad happens.
You'll also see that when a guy tries to grab a woman who's walking by, makes a crude sexual comment, or just keeps talking when a woman isn't interested, that the woman's feelings might escalate and she'll respond negatively.
You can watch what works and what doesn't right in front of your own eyes.
This will start to reprogram your mind that women don't usually "reject" men, even in the most intense situations where they're being approached all night.
2) Start small.
If you have to, start by talking to women who are paid to talk to you. Go to a mall (one of my favorites).
Stores in malls hire attractive young women. Walk into every store, and start conversations. Practice making eye contact.
Come up with a few jokes that you can use in any situation ("So, do you own this store? Perfect, then you won't care if I just take some things...")
Ask the salesgirls to smell your new cologne (the one you sprayed on your wrist next door) and give you her opinion.
The more you do this, the more you'll get used to starting conversations with women you don't know, and having comfortable conversations.
3) Choose one default thing for each situation.
It amazes me that guys don't think ahead. They don't plan what they're going to do. As the old saying goes "By failing to plan, you plan to fail".
You really need to figure out a default thing you can do to start a conversation with any woman, anywhere, anytime.
Once you come up with your idea, mentally rehearse it until you could do it in any situation. Then get out and do it.