i say go on the 'double date' type thing. tell her you may have to bounce because you've got some other 'important things' to do. make it something that sounds FUN. cause thats all that women want, 'girls just wanna have fu un.' shit is so true man. anyways, if you get bored of the women, use that excuse. women will want something that they have to work harder to get, not something that is just gonna roll over like a bitch. pardon the pun. but the fact you're seriously considering going on this stupid shenanigan is INCREDIBLY indicative that you need to work on your self esteem levels. to be blunt, you definitely don't sound like someone with their head on their shoulders. SO,
1. next time you're walking past a girl who gives you good eye contact, smile and say 'hi'. do that EVERY TIME YOU GET THE CHANCE FOR 2 DAYS. that'll help you get over the 'OMYFUCKING GOD IT HAS A VAGINA' itis. or whatever you wanna call your fear of poon.
2. look up david deangelo's 'on becoming a man' on youtube. play that while you fall asleep, mother fucking brilliant. then the day after you play it while you fall asleep, WATCH him as he speaks.
3. self talk: you obviously think about yourself negatively or in a way that doesn't boost your confidence/self esteem. quit being a bitch and start being a man. the boy must die.
4. memorize this shit, and start using it. it's some of the most fascinating insight i've had into the human psyche for a time.
http://www.changingstates.co.uk/nlp_basics.html
5. don't be afraid to be the bull.