How to Talk to Boys

#1 More Conversation Starters
"I’m trying to decide between [two options for a snack/drink]. Which one do you think is better?"
Asking for his opinion on a simple choice can engage him and make him feel helpful, opening the door for more conversation.
"My friend told me this [game/app/song] is awesome. Have you tried it?"
Referencing something a friend recommended makes it sound less like you're randomly approaching him and more like you're seeking advice or confirmation.
"That’s a big [book/graphic novel/comic book]! What are you reading?"
Commenting on something he's reading or carrying can lead to a conversation about his interests or even a recommendation exchange.
"That's a cool [drawing/doodle] you’re doing. Are you an artist?"
If you see him drawing or creating, complimenting his work is a thoughtful way to show interest and can open up a conversation about his talents and passions.
"Hey, I really like your [band t-shirt/backpack/shoes]! Where did you get it?"
This is a great, low-pressure opener. Complimenting something he's wearing that expresses his interests shows you've noticed him and can lead to a discussion about shared hobbies or styles.
"Hey, is that the new [game console/phone]? How do you like it?"
If he has a new tech gadget, showing interest in it can be a good way to get him talking about something he's probably excited about.
"This [coffee shop/park/arcade] is usually so [quiet/busy]! What do you usually get here?"
Commenting on the environment you're both in can open up a conversation about favorite spots or habits.
"Wow, you finish your [food] so fast! Are you always that hungry?"
A slightly flirty and playful observation about something casual he's doing can be disarming and lead to a lighthearted conversation.
"Sorry, do you know where the [restrooms/checkout/specific store] is? I’m still kind of new around here."
Pretending to be new or a bit lost, even if you're not, can elicit help and create an opportunity for him to show you around or give directions.
"Hey, I heard [news about a local event/new store opening]. Are you going to check it out?"
Referencing a piece of local news or an upcoming event can be a natural way to engage him in a discussion about things happening in your community.
"Do you know where they sell [specific snack/drink] around here? I'm starving!"
A direct question about food or drinks in a casual setting can be relatable and lead to suggestions or even an offer to get something together.
"Oh my gosh, is that [new video game]? I’ve been wanting to try that out!"
If he's actively engaged with a popular interest, reacting with genuine curiosity is a strong starting point. It provides an immediate, clear topic to talk about.
"This [weather] is crazy, right? Are you doing anything fun today?"
Commenting on shared environmental factors like the weather can be a simple, universal icebreaker that can lead to talking about plans.
"You seem to know your way around this [place]. Do you come here often?"
A bit more direct, this acknowledges his familiarity with the location and invites him to share more about himself.
"I saw you at [the skate park/the concert/the game] last week! You were [description of something he did]."
Recalling seeing him at a past event shows you've noticed him and can lead to a conversation about shared experiences outside of school.
"You’re pretty good at [sport he's playing/video game he's playing]. Do you play often?"
Observing his skills in an activity he's engaged in allows for a genuine compliment and opens the door to discussing his hobbies.
"That’s a [cool/funny] sound your [bag/phone] just made! What was that?"
Reacting to an unexpected sound or object he has can be a fun and lighthearted way to start a conversation, showing you're observant.
"Oh my gosh, is that [name of a popular celebrity/song/movie]? You have good taste!"
If you recognize something he's listening to or looking at that's culturally relevant, it shows you have similar interests and can spark a deeper discussion.
"(Drop pen near him) Oh, shoot! Could you grab that for me? Thanks!"
A simple, intentional action that requires his help is a low-pressure way to get his attention and initiate a quick exchange of words.
"Sorry, do you know when the next [bus/train] comes? I think I missed mine."
A practical question in a public setting is a simple, direct way to initiate contact. It requires a straightforward answer and can naturally lead to follow-up questions.
"Hey, is your [phone/laptop] having trouble connecting to the Wi-Fi too?"
Using a shared technical issue in a public place like a coffee shop or library can create an immediate common problem to discuss.
"(Smile and hold eye contact for a moment, then look away shyly when he notices)"
A non-verbal cue that lets him know you've noticed him and are potentially interested, inviting him to initiate. This is higher risk as it relies on his initiative.
Difficulty Score
60%