40+ Hard Questions To Ask Your Boyfriend
Sometimes, the most important conversations aren’t the easiest ones. These hard questions aren’t meant to start a fight—they’re about honesty, clarity, and making sure you’re both on the same page. If you’ve been together for a while or things are starting to get serious, asking the tough stuff shows you’re invested and paying attention.
You don’t need to ask them all at once. Just pick a few when the moment feels right. It’s not about putting him on the spot—it’s about making sure you’re building something real.
Have a look at our favorite Couple’s Games here
Hard Questions About the Relationship
- Do you ever compare me to your ex—even a little?
- Is there anything you’ve wanted to say to me but haven’t?
- Have you ever thought about breaking up with me?
- What’s something I do that makes you feel less connected to me?
- Do you feel like I listen to you enough?
- Is there a part of our relationship you’re not totally happy with?
- What’s something I don’t understand about you yet?
- Do you feel emotionally safe with me—really?
- Are you still as attracted to me as you were in the beginning?
- If we had a serious fight, would you fight for us or shut down?
Hard Questions About Trust and Honesty
- Have you ever lied to me—even about something small?
- Do you think it’s okay to keep little secrets in a relationship?
- Is there anything from your past you’ve hidden because you’re afraid I’d see you differently?
- Have you ever looked through my phone or felt tempted to?
- Do you fully trust me—or are there things you still question?
- Do you ever hold back the truth to avoid hurting my feelings?
- Have you ever flirted with someone else while we were together?
- If someone came to me with a story about you, would your first instinct be to deny it—or explain it?
- Would you tell me if you started catching feelings for someone else?
- Do you feel like I trust you completely?
Hard Questions About the Future
- Do you see a future with me—or are you still figuring that out?
- What’s something that could make you change your mind about staying with me long-term?
- Are we moving at the pace you want, or are you just going with it?
- Could you see yourself marrying me someday—or is that too far off to picture?
- Do you want kids—and if so, how soon?
- Do you think we want the same kind of life in 10 years?
- Would you be willing to make sacrifices for our future together?
- What would you do if I got a job across the country?
- If we stayed the way we are right now forever, would that be enough for you?
- What are your real fears when you think about our future?
Hard Questions About His Personal Growth
- Do you think you’ve changed since we started dating?
- What’s something you’re struggling with that I don’t know about?
- Do you ever feel like you’re falling behind in life?
- What part of yourself are you trying to work on right now?
- Do you think I help you grow—or just keep you comfortable?
- Are you truly happy with where you are in life?
- What’s something you’re scared to fail at?
- What do you wish people understood better about your goals or dreams?
- Do you feel supported by me—or just tolerated sometimes?
- What’s one thing holding you back that you’re too scared to admit?
Have a look at our favorite Couple’s Games here
We are Mary and Eric, the founders of Be Right Back, a blog dedicated to romance around the globe and at home.
We are Mary and Eric, the founders of Be Right Back, a blog dedicated to romance around the globe and at home. With over 10 years of experience in dating and traveling to romantic places, we share our favorite date ideas and romantic destinations to help couples level up their relationships. Having lived in and traveled through the USA, we also share our favourite things to do in the States.
With 70,000 monthly readers and 16,000 followers on social media, Be Right Back is your go-to resource for romantic trip ideas and couple activities at home and abroad.