- Keep busy with lots of activities and interests, and maintain your close friendships. This will ensure that you are busy and seldom lonely, mostly eliminating the awkwardness and creepiness that come from desperation.
- Strike up conversations with random people you encounter—not just attractive women, but also men, children, old people, and women whom you do not find attractive. People you don’t find attractive will be easier to talk to, simply because you will be less nervous. I’ve found that older people are usually very approachable, and are also often glad to have someone to talk to. They have a lot of life experience too, so you will probably learn something you didn’t know each time you speak with an old person. The key here is to get practice in talking to strangers. The more practice you get with it, the easier you will find it. Do this for several weeks or a month, until it begins to come naturally to you.
- Chat with at least one woman whom you find attractive every day, but with only the goal of having some nice conversations, spreading a bit of friendliness, and getting practice. Do not ask for her number or other contact details. Provide yours only if directly asked. In other words, plan from the beginning of the conversation to say goodbye without any expectation of seeing her again. Seriously. This is important. The key is to have fun and relax, and not be invested in a particular outcome. Don’t be upset or offended if your friendliness is met with coldness or hostility. You have to remember that you don’t know what sorts of experiences other people have had. Not everyone will appreciate your friendliness, and that’s okay. Just move on and try not to take it personally.
- After a month or so of that, you should be able to move on to a more assertive approach, where you express your interest more directly. Continue flirting with lots of people, including one attractive woman per day. Be straightforward but respectful. Be clear about your interest, but do not be blunt. Remember that her wishes are equally important. Pay attention to her tone of voice and body language. Be wary of letting wishful thinking cloud your judgement. And again, do not expect a particular result. Gracefully accept rejections, glad in the knowledge that you’re still getting practice, and there will be more opportunities for fun flirtation the next day!
Any other suggestions or ideas?