There’s not much worse than the moment you’ve realized the conversation has died. Those awkward moments as you try to think of something to say can really kill a moment. That’s okay! We’re here to help. We’ve curated a list of both thought-provoking and lighthearted questions to ask your boyfriend. Even better, we’ve included tips on when to ask more serious questions, when to keep things casual, and how to avoid making it weird.
How Good conversation Starters Help Relationships
When you integrate icebreaker questions or conversation starters into your relationship you can increase emotional intimacy. By asking your boyfriend meaningful questions like, “What is your holiday or favorite memory?” you can connect on a deeper level. When you dive deeper with questions such as “What’s your biggest dream or the best advice you ever received?” you create opportunities for trust and vulnerability. Finally, when the two of you are able to reflect and share about past relationships you can find shared experiences. Ideally the questions you ask your boyfriend allow you to learn more about one another and just keep things interesting.
Asking Deep Questions
You’ll want to have some deep questions to ask your boyfriend that help you get on the same page with your future goals, values, and priorities. Ask questions on how they define success, their biggest regret or their role models to gain a better understanding. When you inquire about experiences or preferences like the best gifts they’ve received or favorite dates they’ve been on, you make it clear you value their happiness.
Finally, ask questions during tough times so your boyfriend will feel heard, and ensure your bond remains strong. Guys like to know that you care what they think. Plus it gives them an opportunity to open up and ask you a few questions in return.
Asking Lighthearted Questions
Don’t be afraid to use lighthearted questions to ask your boyfriend about himself. Not every conversation has to be deep or serious. In fact, early in your relationship, these questions can help you get to know one another, laugh together, and prepare you for diving into deeper topics later on. Keep things fun and engaging with questions like “What’s your favorite move?” or “What’s the craziest thing you did as a teenager?”
Also, these fun questions can keep the spark alive and rekindle those feelings that take you back to your honeymoon phase – even when you’ve been together for years. That’s something you’ll want in a long-term relationship. So, get familiar with him while enjoying some laughs together.
Make it Fun And Get to Know Him With These Questions
Here’s a list of winning questions to ask your boyfriend along with a few tips on timing and framing. Pick and choose a few that best fit your relationship dynamics.
Do You Have a Go to Karaoke Song?
This is a great first date question to ask your boyfriend. It’s a fun icebreaker, and can help you learn more about him. If you’d like to plan a future date, this is great information to have!
What’s Your Favorite Love Song?
Who doesn’t love music? Any question you ask that helps you find common musical ground is a good thing. Besides, learn a guy’s go to love song and you’ll probably learn just how badly he’s had his heart broken.
What’s The Most Interesting Thing You’ve Eaten?
Are you a foodie? If your vision of a great relationship with a guy includes going out to eat or cooking together, this is a great icebreaker. Cause, are the two of you really compatible if the most exotic thing he’s ever eaten is a Big Mac?
What Was Your Most Embarrassing Moment?
This fun convo starter can lead to a laugh for both of you. It’s also a great way to learn if your new man has a sense of humor about himself.
Do You Have a Favorite Holiday?
Can a Halloween gay and a Christmas gay work out in the long run? Ask him his favorite holiday to see how compatible you are.
What Was Your Childhood Best Friend Like And do You Still Hang?
Is he up for a committed relationship? If he’s had the same bff since elementary school, you can bet he knows how to make a relationship last.
Tell me About Your Favorite Childhood Memory
People love to talk about their favorite things. Get to know him better, and learn what makes him tick with this fun question that takes a trip down memory lane.
What’s Your Favorite Disney Movie?
Learn about his favorite movie, and see if he’s a Disney gay!
Are You a Morning Person or a Night Owl?
Can your relationship last if one of you stays up all night and the other’s an early bird? Better see if this important life compatibility is there!
What’s The Trick to a Healthy Relationship?
This question digs deep into his core values. It may not be a question for when you’ve just started dating, but you’ll want to ask it eventually.
What Would Your Dream Job Be?
Most of us like to talk about our fantasy jobs, even if they don’t align with our reality. What would he do for a living in another life!
Do You Have a Favorite Ice Cream Flavor?
Does he go for classic flavors like chocolate or strawberry? Does he prefer something a bit more gourmet? Ice cream is one food that people have big feelings about. Just remember that just because he loves vanilla doesn’t mean he is vanilla!
Do You Have a Celebrity Crush?
Some of us have our first crush on that cute boy who was in our middle school history class. Some of us fall madly in love with a musician or actor. Even as adults we crush on celebrities. So, why not see if your crushes align! He may even introduce you to a new person to admire.
What’s Your Hidden Talent?
What kind of special skills does he have? Of course, if you ask this, you better be prepared to answer the same question in return. This could turn the conversation spicy!
What Was Your Favorite Toy When You Were a Kid?
Let’s be honest! Guys love toys, and that doesn’t stop when they grow up. Who doesn’t love to reminisce about the super cool things they played with as a kid???
Tell me The Funniest Thing That Ever Happened to You on a Date
We’ve all had dates that were “interesting”. Sometimes, all you can do is laugh. If a sense of humor is important to your relationships, this question helps you gauge his ability to laugh in any situation.
What is Your Love Language?
Yeah, love languages aren’t a real thing, and the guy who invented them is a bit of a creep. Still, this is a good way to learn how he might show affection in your relationship.
What Weird Thing do You Find Attractive?
Maybe you think your best attribute is your smile or sparkling blue eyes. That may not be the case. The guy you’re dating could be turned on by that little scar over your eyebrow or the way you tap your foot when you’re anxious. You never know what makes his heart beat faster.
Who Was Your First Guy Crush? First Kiss With a Guy?
Everybody loves a great, gay awakening story time! So, start a convo about how each of you first started crushing on dudes.
What’s Your Favorite Thing to do on a Rainy Day?
Is this relationship going in the right direction? If his ideal rainy day activity involves spending time with you, then you know you’re on the right track. This is also a great question if you’d like to plan a rainy weather date.
Do You Have a Comfort TV Show?
What’s a comfort show? It’s that one show you go back to over and over, no matter how many times you’ve watched it. The two of you might share a love for the same nostalgic TV series, or you might be able to turn one another on to something new to watch.
What is Your Idea of a Perfect Date?
Are you looking for questions to ask to learn how to impress your new guy? This is a great way to find out exactly what he enjoys.
If You Could Live as a Fictional Character Who Would it Be?
Here’s another great question to ask when the conversation dries up a bit. It’s also a bit aspirational, since people tend to admire characters who represent their life goals.
Let’s Talk About Your Favorite Movie! What About Favorite Disney Movie?
Disney movies are life! Besides, people love to talk about their favorite movies. So, this one is always a winner when you want to keep the conversation fun and engaging. Use this to plan a great movie night for an upcoming date.
Do You Think We’ll Stay in Our Honeymoon Phase Forever?
You’re a few dates in, and your new relationship is going well. Why not talk about the beautiful thing known as the honeymoon phase? It’s a great way to get into how amazing things are right now, and look towards the future a bit.
Random Fun And Flirty Questions to Break The Ice
There are so many great questions to ask your man! Let’s keep things going with a list of questions that work in any stage of your relationship.
- What was your favorite subject in school?
- Do you believe in love at first sight?
- If you made me dinner, what would you cook?
- How important are first impressions to you?
- What was the best thing about your last relationship?
- What’s your favorite life hack?
- We’re playing Mario Party. Who’s your character?
- What’s your favorite smell?
- What’s the best concert you ever attended?
- Would you rather go to the beach or the mountains?
- What’s the strangest life advice you’ve ever received?
- If you had to eat the same food every day, what would it be?
Questions to Avoid or Delay?
Someone once said there are no bad questions. Well, that’s not true. There are bad questions to ask your boyfriend. At least there are badly-timed or inappropriate questions to ask your boyfriend. Think twice before you:
- Ask too much about their personal life too early in a relationship
- Ruin a fun mood with too many deep questions
- Question them about a past relationship too soon
- Hit them with questions that might be triggering – for example their biggest fear or childhood memories
- Bore them with questions on things that don’t interest them – like pop culture questions for someone who just isn’t interested in that at all
- Make them uncomfortable by asking questions that assume you are in a deep or committed relationship too quickly
- Ask Political or religious questions – unless these are relationship dealbreakers for you
- Get into inappropriate or dirty questions too soon
- Ask relationship questions or romantic questions that come off as pushy
The most important lesson here is to keep things flowing, and maintain a natural conversation. This isn’t a job interview. Nobody wants to feel like they are being peppered with random questions. That’s a quick way to put someone in a bad mood or make them feel uncomfortable. Also, remember that these questions to ask your boyfriend can be rephrased so they fit into your date conversations naturally. Think of them as icebreakers or conversation starters. Then, adjust as necessary or choose which questions are appropriate for this stage in your relationship.
Ask Away!
Ask great questions to keep the conversation flowing, learn more about your guy, and show curiosity about his life. With the right questions, you make things interesting, and let him know that you genuinely care about his thoughts and opinions. That’s how amazing relationships grow!
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