60+ Trick Questions To Ask Your Boyfriend

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Sometimes, you just want to test the waters a little—and trick questions are perfect for that. Whether you’re on a first date trying to gauge someone’s honesty, wondering why your boyfriend strolled in two hours late, or figuring out if he’s really ready to take the next big step, these questions let you read between the lines without getting too serious too fast.

They’re sneaky, but not mean. And if he catches on? Even better. That means he’s paying attention.

Have a look at our favorite Couple’s Games here

Trick Questions To Ask On A First Date (To Make Sure He’s Honest)

1. If I told you I’ve been Googling you, what would I find that you forgot to mention?
2. What would your last girlfriend say was your worst habit—and don’t say “none.”
3. How many people have you said “I’ve never felt this way before” to?
4. If I asked your best friend to describe you in three words, would any of them be a red flag?
5. What’s something you’ve “never done” but wouldn’t be surprised if someone accused you of?
6. How many dating apps do you currently have on your phone?
7. If I looked through your camera roll, what photo would you hope I didn’t find?
8. Have you ever been ghosted—or have you done the ghosting?
9. If your ex walked in right now, would things get awkward?
10. On a scale from 1 to “I need therapy,” how over your last relationship are you really?
11. Would your mom say you’re a gentleman—or would she pause before answering?
12. What’s one lie people often tell on first dates that you’ve definitely used before?
13. If I asked you to tell me the truth, would you say something you hadn’t planned to?
14. If I asked your last date what went wrong, what would they say?
15. What’s something people assume about you on dates—and are they right?
16. If I asked how many people you’re texting right now, would your answer include group chats only?
17. When was your last “I’m not looking for anything serious” phase?
18. If I asked you to hand me your phone right now—would you hesitate?
19. What do you think is more important on a first date—honesty or chemistry?
20. If I said, “Tell me something that would make me run,” what would you say?

Trick Questions To Ask When Your Boyfriend Comes Home Late

1. What color were the walls where you weren’t tonight?
2. Who were you with—and who else just happened to be there?
3. Why didn’t your phone die when you were scrolling Instagram but did when I texted?
4. What’s your favorite thing about where you just were? (Ask for details.)
5. What’s the last photo you took today? Let’s look at it together.
6. If I call the person you were with, what would they say you were doing at 9:17 p.m.?
7. What song was playing wherever you were?
8. Can I see your location history just for fun?
9. What’s something about tonight you wouldn’t want your mom to know?
10. What’s the one detail you rehearsed before walking through the door?
11. Why didn’t you just FaceTime me real quick if you were free?
12. If I asked you to explain what took so long—with timestamps—could you do it?
13. What time did you plan to come home vs. what time you actually did?
14. If I had a camera crew following you, would I be bored or shocked?
15. Did anyone unexpected show up tonight?
16. What excuse would you have used if I hadn’t asked where you were?
17. What were you wearing—and does it match what’s on your Instagram story?
18. What’s the part of tonight you’re skipping over on purpose?
19. If you could swap nights with someone else and have no one know, would you have done it?
20. Do you want to say anything you think I already know?

Trick Questions To Make Sure He’s Ready For The Next Step

1. If we moved in together tomorrow, what would be your biggest adjustment—besides giving up half the bed?
2. What’s more stressful: meeting my family or planning a future with me?
3. If I handed you a key to my place, would you be excited or slightly sweaty?
4. If I asked, “Where do you see this going?” would your answer involve a timeline—or just vibes?
5. What scares you more: commitment or saying the word “commitment”?
6. If I said I was ready for the next step, would you ask “Which step?” or just nod and hope for the best?
7. If we made a shared calendar, would you put our anniversary in it or “forget accidentally”?
8. What would you do if I gave you a drawer tomorrow? Fill it or panic?
9. If I asked you to plan a weekend getaway for us, would you book it—or say “we’ll see”?
10. What’s one thing you still want to do solo before doing it as a couple?
11. Do you see us in five years… or are you still figuring out what you’re doing next weekend?
12. What’s more terrifying—planning a wedding or planning a future budget together?
13. If I asked how many kids you want, would you answer with a number or a joke?
14. If we adopted a pet together, would you call it our dog or my dog?
15. What’s one “serious” conversation you’ve been avoiding lately?
16. If I got offered a job in another city, would your answer be “I’ll visit” or “Let’s figure it out together”?
17. Are you saving up for something just for you—or for something for us?
18. Would you rather take a relationship quiz or talk about what we want next?
19. What does “long-term” mean to you?
20. What’s stopping us from taking the next step right now?

Have a look at our favorite Couple’s Games here