14 “Deep” Questions To Ask Your Boyfriend That Will Actually Make You Closer
Valentine's Day is next month, so it's time for a little tough love. Are you ready? Deep breath... You're not going to get far in your relationship by wondering, "What are we doing?" anymore. For such a simple question, it carries the weight of being vague and loaded. It's not that you shouldn't want to know where your relationship is headed, but there are better questions to ask your boyfriend.
From my first relationship to being engaged with an energetic toddler, I know a thing or two about how to broach certain topics. But, I'm no one's expert so I turned to Sean O'Neill, a Licensed Marriage and Family Therapist and Clinical Director at Maple Moon Recovery, to help you figure out how to get to the heart of your relationship.
Scroll to see which deep questions to ask your boyfriend for a better, healthier relationship!
1. Questions To Ask If You're In The 'Honeymoon' Stage
Whenever we finally move from flirting with our crushes to being in a relationship with them, it's typically followed by a period of euphoria. You and your boyfriend likely can't get enough of each other right now which is probably making your friends playfully roll their eyes. Since everything is brand new, you can still keep it light though.
O'Neill suggests asking "open-ending questions that prompt curiosity and connection:"
- What's one dream you've never let me in on?
- What's one little gesture that can make you feel valued?
"These couple of queries facilitate bonding while generating enthusiasm for the goals and interests of each other," he says.
2. Questions To Ask After Your First Big Fight
Even if you and your boyfriend are super tuned in to each other, a disagreement or argument is bound to happen. In case you're worried, your relationship isn't on thin ice because you're not seeing eye-to-eye on something. O'Neill says you can ask:
- How do you think we handled the argument?
- What could we do differently next time to make our future fights more productive?
His reasoning is that these questions "promote growth and empathy" so "disagreements are transformed into stronger communication opportunities."
Note: Disagreements should never turn physical. It's not okay for you and your boyfriend to become physically aggressive with each other. If you're concerned about domestic violence, dial the National Domestic Hotline at 1(800) 799-7233.
3. Questions To Ask Before Introducing Your Boyfriend To Your Parents
Introducing your boyfriend to your parents is a huge step that can be scary and exciting. I was terrified when my parents first met my fiancé because they couldn't stand my ex. But, the conversation between them flowed and everyone always looks for him to be at family events.
If you're ready for introductions to be made, O'Neill wants you to "encourage the normality of preplanned talks" by asking:
- What is something about me that you think my parents would really love to hear about?
By doing this, he says it'll "help alleviate anxiety and ensure both spouses feel comfortable and attuned before meeting the parents."
4. Questions To Ask If You Or Your Boyfriend Have An Illness
It's never easy to experience illnesses or health scares, but it can be terrifying if you don't know how to help your partner manage if something unexpected happens. O'Neill says to "nurture insights with queries such as:"
- What is one thing I could to assist you better when ill?
- Are there any aspects concerning your healthy that haven't been discussed which make you anxious?
"The conversations provide a safe space for airing concerns while building up mutual support through health difficulties," he adds.
5. Questions To Ask If You're Worried About Boyfriend's Spending Habits
Financial red flags are always a cause for concern when dating someone — especially when it seems like your boyfriend doesn't care about his spending habits may affect your household if you live together. O'Neill suggests asking:
- What are your financial goals?
- How do you see us working towards them together?
- How do you feel about budgeting as a team?
This will "make goal alignment stronger" because "effective communication about finances can prevent misunderstandings," he says. Also, this helps "lay the foundation for a shared vision of the future."
6. Questions To Ask To Deepen Vulnerability With Each Other
Being vulnerable isn't easy for everyone, let alone two people in a relationship. It took me years to feel comfortable expressing my sadness or fears to my fiancé because I was afraid he'd think I was 'weak.' However, this can cause more harm than good because it becomes difficult for our partners to know what's going on with us if we don't open up.
O'Neill says you can ask:
- What's one fear or concern you've hesitated to share with anyone before?
- How can I help you feel safe sharing with me?
7. Questions To Help Move The Relationship Forward
If you're still wondering "what are we doing" after asking some of the above questions, you focus on asking the following "future-oriented questions," according to O'Neill:
- Where do you see us in 5 years?
- What's something you envision us doing together as a couple in the future?
But that's not all! We have more advice about relationships if you're looking to build a deeper connection yourself, friends, or family in 2025!
