Today's Dating Question! [View All]

[Bennyboy]

Sunday I went to a Super Bowl party at a friends house. My friend's sister (Anne)comes over to watch a little of the game. She is incredibly beautiful and we talk for while. We have a lot in common (except she was showing off her new Eagles CD---YEACH!)including age, and got along well. Before the game was over she had to leave to pick up her daughter (21)and left before I could ask her out.(I am really shy in that type of situation).

As there were a few men in our age group at the party, the second she left the talk turned to Anne. Dave told us all about her and her soap opera type past. Seems she has been really really really screwed over by every man she has ever been with. The one thing he says is she is single and "and no man can deal with her" according to my friend.

Of course, that does nothng to deter me. I love the challenge and am completely opposite of the type of man she has been with before as far as the way I treat the ladies in my life.

As all the other men were there, I felt a bit uncomfortable asking Dave for her number at the party. I didn't know if I was going to ask him for her number later anyway, that kind of puts pressure on him and was not sure of that either.

He did let it out where she works and thought maybe I could go there and show up as she went to lunch and ask her out for lunch or even after work. This method has worked in the past. Big Matzoball.

Then this morning he sends me an email that originated from her work email account. So now I have her email addy. As I did not get the email directly from her, it seems kind of weird to send her an email asking her out.

So, my question is: Do I ask Dave for her number? Do I go to her work and wait till she comes out and ask her out? Send her an email asking her out?


I don't hang out in bars and don't get much chance to meet many women, but Anne seems like someone that I would like to see some more. As I am fairly new to the dating scene I am not sure what to do. HELP ME, PLEASE, WISE SAGES OF DU!