Hi again, Cameron.
I see that you are offline, so I have changed to the Q&A format.
If you could answer those questions I posed in the Chat box, it would be helpful, but for the moment, I'd like to send you an answer and if you have any additional questions or concerns, please feel free to click reply and we can continue our conversation.
In situations as you describe, it's usually the fear of rejection that will make you feel shy and/or less confident to ask a woman for a date and/or go out on a date with her. If you work on your self-esteem and act and look confident, the woman will feel this too, and be more likely to accept your invitation for a date.
The thing is, to take things slowly; first ask a woman you're interested in, to go out for a drink or coffee so you can talk and get to know each other better, talk and begin a friendship. This will also help you feel more confident because it will be a very informal situation and you shouldn't feel 'pressured'. Just be yourself and speak to her easily and smoothly. If you want to write down a few subjects to discuss, this should also help, and you can keep the list in your pocket and refer to it, if necessary, while taking a trip to the loo, etc. Simple topics like asking her about herself, her family, her work, how long she has lived in this area, discussing the weather, etc. Tell her some interesting things about yourself, too, like where you work, what you like to do in your time away from work, what kinds of music you like, etc.
Just talk to her like you're talking to a friend; keep telling yourself that there's no reason to be nervous or feel timid. You're a person, she's a person, you're getting to know her better, and all will be well. You might even memorize a clever short joke to tell at an appropriate moment. Laughing is always a great ice-breaker!
A good idea is to 'practice' with a female friend or relative before you actually ask someone out. They can give you their feedback on how you sound and make suggestions for improvement, depending on what they would like to hear when they're out with a man, in a hypothetical situation.
It would also be a good idea to go to a counselor or therapist to learn why you feel so timid and fearful about dating women. It may be related to an experience in your past, or just a natural shyness, but a therapist would be able to give you some exercises to work on to help your situation.
There are also a lot of great books you might want to read to help you gain confidence.
I hope you have found my answer helpful and everything will work out well for you in the future!
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