Ask him about himself

"So, Ryan, tell me more about yourself."

Ryan blushed for a bit before stammering out, "What's there to know? I'm just an average guy."

You give him your best smile, "I think you should let me be the judge of that."

"Well, my family moved to this town 2 years ago. My dad is in the military so we moved around a lot when I was younger but he's now taking an administrative role here locally so I don't think we'll be moving anytime soon. It was hard at first but I've gotten used to meeting new people and developing new relationships," described Ryan, "My mom is a home-maker. She spends most of her at home, taking care of the house and stuff. As for siblings, I have an older sister but she's now in college. I don't get to see her much these days except maybe for Thanksgiving and Christmas."

He stopped himself and looked at you apologetically, "Sorry. I've been rambling."

"I don't mind," you reassured him, "Besides, you haven't really told me much about yourself yet."

"Well, umm..." he stammered, "I used to play lacrosse in my old school but dropped it when we moved. I'm now mainly into photography."

"Of what?" you asked, genuinely curious.

"Random things, really. Haven't really decided on it yet," he replied, clearly much more comfortable with you now.

Wanting to shake things up a bit, you quickly changed the topic and asked, "You seeing anyone?"

"No. Am very much single," he responded, "Haven't really thought about it really."

"Well, you have an impressively nice smile, Ryan,"

He blushed at the comment but managed to hold his composure to mumble out a "Thank you".

The rest of the drive is uneventful and after a few more minutes, you quickly find yourself alone with him in your garage.