Should I or Should I not?

So, this story happens before the truth or dare thing. It tells you more about how Josh feels about himself and how he feels about Serena. Sorry for the arrangement :(

It was a sunny afternoon. Serena and Josh were at Josh's place. Serena wanted to borrow some of Josh's books which by the way is heaven for Josh. He can't begin to describe how much he loves this girl. Yes, loves, you heard right. They have been friends for about 6 years now, since Josh moved into town. But, unfortunately, Serena just sees Josh as her older brother (or so he thinks).

Serena: Thanks for the books Josh.
Josh : No problem.
Serena: Hey, I've got to go because I have my tuition class in a couple of hours, so? I'll see you later.
Josh : Yeah, sure.

Once the front door was closed however, Josh's father, Mr Tate spoke up from the corner where he was previously looking on.

Mr Tate : You know, you should really ask her out, you know, like out here?
Mr Tate gestured to the surrounding.

Josh scoffed.

Josh : Yeah right. That will never happen. She looks at me like an older brother. A strictly no date
         relationship.
Mr Tate : And how do you know that? You'll never know if you never try.
Josh : I know because I hang out with her all the time, dad.
Mr Tate: Look, could you at least try?
Josh : You know what? Thanks dad. I can see us on a date right now. Do you know how it ends, dad?
Mr Tate :No, I don't. How does it end?
Josh : Ok. Picture this, Serena and I  are on a date, let's say in a cafe.  We're talking, she laughs, pretends I'm
         funny, then suddenly, nature calls and I have to go to the gents room. I'm thinking how great our date is
        going and then I make my way back to our table and what do I see? Do you know what I see dad?
Mr Tate: No. But, I don't like where this is going.
Josh : Oh, it is going to get worse. I see her talking to a couple of guys. She looked so happy, laughing, and
          talking to the guys. Then, she gets up and leaves with them, forgetting all about me. Now, that is
         exactly what's going to happen.
Mr Tate : Oh come on! Be positive. I'm sure it will turn out differently.
Josh : Dad, I love you but, sometimes your happy go lucky attitude annoys me to death.
Mr Tate : "Whatever"

Mr Tate impersonates his son.

Mr Tate : Just curious, why do you picture it like that?
Josh : I don't know, dad. Isn't it obvious? She's a very beautiful girl. Anybody would kill to go on a date with
          her.

Mr Tate chuckled.

Josh : What?
Mr Tate : Nothing, it's just that you called her beautiful. She must be special for you to call her that.

Josh smiles to himself and says,

Josh : She sure is.
Mr Tate : Yeah well, think about what I just said. If your prediction does come true, than she does not
                deserve you.

With that, Mr Tate leaves his son in alone to his thoughts. Now it is up to Josh to decide....
Josh