Asking a complete stranger out and going on a blind date!!

So basically everyone knows I am ShY. So anything that has to do with dAtInG and BoYs is a real struggle for me... Here are two things that I looked back and think "DaNg Cori, What were you smoking?!?!" Um first asking a complete stranger out... Boy was that nerve racking... It started a few summers ago when my two amazing sisters worked at the Scera Shell ( taking tickets) I decided to go help them for a few weeks during the play Fiddler on the Roof. (love the play by the way) I noticed this boy that was in the play and just admired him from afar... His name was/is Steve, but he wore this plaid shirt so Jaime, Whitney and I called him luke. Because Luke on gilmore girls always wore those type of shirts... And of course Whitney and Jaime knew I thought he was extremely good looking. So they would always say "Luke Luke Luke" and every time he would walk by instead of saying his name they would be like "Hey Cori, Its Luke" Well it was the last day and basically my sisters dared me to ask him out. So it was like 2 min. before he went on stage and I said to myself "SeLF, Its now or never" So I just marched right up to him and introduced myself and asked if he wanted to go to a concert the next week. He said Yeah, sounds like fun! Then I gave him my number and walked away. He called and we went to the concert, had a blast...
Next going on a blind date... Well I have been on a few of them. Jaime and "Jerold" (we don't talk about him) lined me up with "Jerold's" friend we will just call him "Bob". So I was like what the hey, Lets do it!! So being old fashion thinking well I am being lined up, either we go dutch or he should pay... Right??.. Boy was I wrong... I paid for the Whole FlIpPiN' date.... We went to Chuck-a-rama, then walked the mall then we went to wait for it.... Yes a hypnotist! I tried to get HypNoTiZeD I was sooo close too... Then they took us home. Lets just say he was Sooo not my type. Now I know that I am a rIoT and all but no matter what I said he laughed He showed me pictures of his dog"(which by the way he carries it with him in his pocket) and he is at his dream job right now as wait for it yes a part time janitor. He sweats like no other and a bunch of other stuff.. And that is why I don't like blind dates.