Talk to him about things you have in common.
“Hey, did you study for that test tomorrow? It’s supposed to be really hard, I’m not feeling too great about it haha.”
Kinda, haha. I was really busy last night so I probably didn’t do as much as I should have.
“Yeah, that was my problem last week. It’s like, can’t you just schedule the tests around all my stuff??”
Yeah, I wish haha. What were you up to last week?
“We had all these dance rehearsals for a recital. It was fun but it took up so much time.”
Oh, I didn’t know you danced. That’s cool.
“Yeah, I have for a few years now, hip hop and contemporary mostly.”
Nice, which one’s your favorite?...
Bring up things you know he’s interested in.
“Hey Will, you’re on the swim team, right?”
Yeah, for the past couple years.
“Cool. I was asking because I have this little cousin that’s trying to learn how to swim and they were like, ‘ask your friends!’ Which was weird, haha, but if you’re looking for some extra money…”
Oh dang, haha. That’s cool of you to ask. I’m super busy now but maybe in the summer? Or I think they do them at the public pool, too.
“Oh yeah, I forgot about that! I wonder why that wasn’t the first place my aunt tried. She was probably like, I want someone with real, professional experience, on a high school swim team, haha.”
Haha, hey, not just any experience, we went to the championships last year!
“Oh of course, how could I forget? Haha I’m just teasing. Which strokes do you do again?”
Give him a compliment, teasing or admiring.
“Hey Logan, I saw you in the play last night! You weren’t terrible…”
Haha, wow, thanks a lot!
“Just kidding, just kidding. No, you guys were actually really good though.”
You still sound surprised, haha.
“Well, it is just a high school play, haha. But no, I was actually pretty impressed. The sets were super cool, too.”
Yeah, they worked really hard on those. And we rehearsed for months, seriously.
“Wow, really? That’s a big commitment. When did you start?...”
Ask him about things going on at school or in your community.
“Justin, you’re in the parade this weekend, right?”
Yeah, I’m playing with my band on this one float.
“Oh wow, that’s cool. Do you know what time it starts? I’m supposed to march with my softball team but I couldn’t remember.”
Haha, did you try texting someone?
“Well, that was my plan, but you were right here… so if you’re useless, I guess I’ll have to…”
Haha. Well, we have to get there at 9:30 in the morning, I think it starts at 10?
“OK, yeah, that sounds right. And that’s cool you’re in a band, I didn’t know that. What do you play?”