Like rocket says, be random and show that you are there to have fun. But keep in mind not to ramble, which is easy to do.
For me, being high on coffee right
before the date helps a lot. (Since I don't usually drink coffee - free radicals, gives you wrinkles.) Just one cup gets me going like the Energizer Bunny.
A quirky tip I heard: Write "f*ck you" on your toes, the letters pointing outward. It keeps you from feeling nervous and stale in a conversation.
I could point you to the DJ Bible and the articles in
Step 7: Conversation. Instead I'll show you
Hot Girl, episode 6 from
The Office, season 1.
http://www.cucirca.com/2008/06/16/the-office-season-1-episode-6-hot-girl/
Skip forward to 18.09, where Jim is going to talk to the girl who sells purses. She is attractive and most of her customers are men, "They buy them as gifts." (Yeah, right.) Through the episode you have seen Michael and Dwight trying to come on to her beta-style. She reacts politely, probably being hit on every day - it's how she sells purses.
So Jim decides to be just casual and quirky with her. And he is NOT gonna buy anything. A short scene but well-written, the delivery is excellent. The dialogue in itself isn't enough, it's about the style in the delivery.
JIM:
"Hi, I'm Jim by the way."
KATIE:
"I'm Katie."
JIM:
"Hi Katie, nice to meet you."
KATIE:
"You sit out there, don't you?"
JIM:
"I do, that's what I'm best known for. Sitting out there. All right, let's talk about purses!"
KATIE:
"Okay, Um..."
JIM (fake serious) :
"Katie, but, you know what? Don't try to sell me one. Okay? Seriously, 'cause I'm just here to learn."
(Katie laughs, by now it's clear Jim is taking charge and Katie is following.)
KATIE:
"Okay...."
And he doesn't let up on this after the initial success. He keeps up the quirkyness later.
JIM:
"All right, now, I'm gonna warn you. Don't freak out, okay?
KATIE:
"Why?"
JIM:
"This is a really nice car. In case you haven't noticed, this is a Corolla. Okay?"
KATIE:
"It's all right, it is a very nice car."
JIM:
"So you're not gonna freak out."