1. You’re Not Going to Bed Yet, Are You?
This will be a subtle little hint that'll let him know you want him to keep texting you. If he likes you as much as you like him, then he'll probably stay up for a little bit longer.
2. Give Me Music Suggestions
Everyone thinks they have amazing taste in music. Show him you care about his opinion by asking for some album suggestions.
3. Did You like My Outfit Today?
Make sure you use a cute emoji along with this text. It'll let him know you're being flirty.
4. Do You like Your Job?
If he's at work, and you can't think of anything else to talk to him about, ask him a simple question like this.
5. What do You Want to do when You’re Older?
If you're both young, he probably isn't working at his dream job yet. That means you can ask him this question to find out what he really wants to do with his life.
6. What Are Your Plans for the Weekend?
It doesn't matter if it's Friday or Monday, because you can ask him this question. With any luck, he'll end up saying he's looking for someone to hang out with, and you can set up a date.
7. Have You Ever Seen Supernatural?
Ask him if he's seen a certain show or movie. If he hasn't, then you can invite him over to watch it with you.
8. What Kind of Car do You Have?
Boys love their cars. That's why he'll be happy if you ask him about his ride.
9. When’s Your Birthday?
If you know this info, then you can buy him a gift!
10. Are You as Tired as I Am?
People love to complain. If you mention how tired you are, he'll probably list off all of the reasons why he's tired, too.
11. What Have You Been Doing?
This sounds like a boring question, but it could actually lead to an interesting conversation.
12. I Need a New Restaurant to Go to
Ask him for his suggestions. He might even offer to take you there himself.
13. Do You Want to See Deadpool?
If he does, then you can ask him to go with you. It's a cute way to hint at a date.
14. Do You Know if How I Met Your Mother is on Netflix?
People love to talk about Netflix, so this isn't a strange question. Plus, it could lead to a conversation about Netflix and chill.
15. Did You Have a Good Day?
This is a simple question that can mean a lot. It'll give him a chance to rant about what went wrong throughout the day.
16. What Kind of Phone do You Have?
People love to talk about their phones. That's why this question should lead to at least a few more minutes of conversation.
17. Don’t Leave Me
Only use this line if you're close enough to joke around. It'll show him that the last thing you want is for the convo to end.