Expert: David - 6/18/2009

Question
QUESTION: Hi I'm 17 and the girl that I like is either almost 17 or already is 17. That's the thing, I don't really know her at all and haven't talked to her since we were in freshman English together, but back then it was just because we were classmates, not because we were friends or anything.

At the end of Sophmore year I saw her at lunch one day and then she was constantly on my mind. I wanted to ask her out, but every time that I planned to do it I chickened out because in the back of my head I kept thinking how weird it was since we didn't know each other at all. In case you couldn't tell already, I'm sort of a shy person. So then summer passed and Junior year came and I still wanted to ask her out, but again, every time I saw I had an opportunity (she was rarely alone), I couldn't get myself to do it. I think she might like me too because after she caught me looking at her a couple times in the hallway, she started looking at me and looking down hallways she knew I would be in, even at the end of the year.

So now it's summer, it's been a year and I know I really screwed up, but I still think about her a lot. So my question for you is should I get her house number out of the school directory and call her since I won't see her again til next year or should I just let it go because I took way too long?

ANSWER: Hey Alex,
First off I've been in the same boat as you many times.  I am a fairly shy person and, although I have a ton of friends that are girls, it is hard for me to get the courage to ask a girl out.  You are in a tough situation right now because you are not going to see her for a while.  Before you call her house I would say that you should try and either find her on facebook or myspace, or network to get her cell phone number, the latter being the better option.  If you do get her number just text her for a little while and gauge her interest.  How does she respond?  Are her messages long?  Is she trying to end the conversation?  If you find her online message her and do the same thing.  Then, once you deem it necessary, just ask her and remember, the worst she can do is say no.  If she says no it is her loss so who the hell cares about her.

If you need any more advice I would be happy to help.

-David

---------- FOLLOW-UP ----------

QUESTION: Thanks for answering the first question. I just have another quick one for you. For a first date I was thinking a movie and maybe dinner. Is a movie enough or should we go to dinner also? And then, since we're only teenagers, should the restaurant be nicer or could it just be like a Potbelly's?

Answer
I'm going to answer that the best I can because I have no idea what Potbelly's is.

Something casual for a first date is usually a big idea because you don't want to be too ambitious.  You should probably go somewhere to eat, but make it a little nicer than McDonalds.  It is always good if it is somewhere where you two can sit and chat.

-David