20 Conversation Starters That Actually Lead to Deeper Connection
Thought-provoking questions to ask someone to know them on a deeper level.
- Cyra Sanchez
- 7 min read
Deep bonds can build up over time on their own. But you can also take the initiative by starting conversations that could lead to something more. Being proactive in building a deeper connection with someone is never a bad idea, it just shows you’re willing to put in the effort. So start by asking some of these conversation starters to connect with someone on a deeper level.
1. “If you could back to the past, would you change anything?”
Andrey Grushnikov on Pexels
Time travel seems like an excellent idea and many possibilities could arise. If you asked someone what they would do if they had the chance to change their past, they could tell you many things and why they would or wouldn’t.
2. “What are your biggest fears?”
Timur Weber on Pexels
You can tell whether someone trusts you entirely if they’re comfortable telling you their biggest fears. This tells you what can hurt them the most or what could turn their entire world upside down. But the good part is, you’ll know what to do to protect or support them from now on.
3. “What are your values and beliefs?”
RDNE Stock project on Pexels
Knowing someone’s values and beliefs is a typical question to ask if you don’t want to sound too personally invading. This question helps you determine whether that person’s beliefs align with yours and whether you agree with their values or not.
4. “What is your love language and why?”
Pavel Danilyuk on Pexels
There are different love languages, and being fluent in them is important to properly express your love for someone. Finding out someone’s love language tells you how they prefer to show love and how they want to be loved. This helps you decide whether you can match each other’s wants and needs.
5. “What is your biggest regret?”
SHVETS production on Pexels
While this may sound like a sensitive question, it can be appropriately delivered immediately. Regret can shape someone’s values and priorities. Knowing someone’s biggest regret tells you what they went through and what lessons they must have learned.
6. “Who are your relationship role models?”
Alex Green on Pexels
Finding someone’s role model will tell you what kind of person they aspire to be. For example, if they say their role models are their parents because of how happy their marriage was, you’d have reasonable expectations from that person, too.
7. “How do you picture your future with your partner?”
Vera Arsic on Pexels
Talking about the future often involves hopes and dreams. It tells you what path they wish to take and what hardships they’re willing to endure to make their future goals a reality.
8. “When was the last time you felt special and why?”
Darina Belonogova on Pexels
Knowing what makes someone feel special is one way to know how to treat them right. This may trigger an emotional yet positive conversation that encourages the other person to examine their feelings and realize their value. Everyone deserves to feel special, so take note of their answer in this discussion.
9. “How do you handle conflict?”
Timur Weber on Pexels
Conflict avoided is conflict prolonged or multiplied; it resolves nothing most of the time. That’s why it’s a good idea to ask someone how they prefer to handle conflict. Do they shut down, or do they face the issue head-on? This will show you the strengths and weaknesses in their communication skills.
10. “When was the last time you were deeply hurt and why?”
Alex Green on Pexels
Encouraging someone to talk about their most sensitive emotions is an excellent way to build trust and connect on a deeper level. Brace yourself in case they get carried away or break down before you. This conversation starter works best when you’re alone, and both have the time to talk heart-to-heart.
11. “Have you ever lied to someone you love?”
Gustavo Fring on Pexels
This difficult question is an excellent way to test someone’s honesty. Can they face their own mistakes, justify their wrongdoings, or genuinely have a good reason to lie to someone they love? With so many possible answers, you’ll have plenty of chances to connect on a deeper level.
12. “What is your dream in life?”
Nothing Ahead on Pexels
Learning about someone’s dreams is a nice conversation to have. They can tell you why they have that kind of dream, what influenced them, and what they’re looking forward to about it. At the same time, you can actively show your support and understanding for them.
13. “What makes a home feel like home to you?”
Kelly on Pexels
There’s a difference between a house and a home, so ask what feels like home to understand better what makes them feel safe and comfortable. They might tell you that home isn’t a place but a person. Sometimes, they might also describe the qualities they seek in a home.
14. “What was your childhood like?”
Artem Podrez on Pexels
Talk about each other’s fondest childhood memories or even the unhappiest ones. This is a quick way to understand them for who they are, how they became who they are today, and what they could’ve been if their childhood had turned out differently. Many people carry something from their past, so don’t miss the chance to connect with their past to build a better future.
15. “What is your favorite memory that makes you smile?”
Kindel Media on Pexels
Learning what makes someone smile helps you understand their joy. It will also show you whether they value the little things the most, so listen closely to the details of their favorite memory. After connecting with them deeply through this, you can make new happy memories together that you can cherish.
16. “If you had all the money in the world, what would you be doing right now?”
Andrea Piacquadio on Pexels
Many people are forced to hold back from pursuing their genuine dreams for multiple reasons, mainly financial troubles. With this question, you’ll be surprised to hear people’s different answers, which may completely change your perspective on their character. Either connect on a deeper level or drift away if the impression turns out wrong.
17. “What is your worst experience with someone in your life?”
Liza Summer on Pexels
They can answer this question with almost anything. It can be about anything: a past lover, someone in their family, a failed friendship, a terrible date experience, and many more. With this, you’ll learn what tests their patience, what offends them the most, what hurts them, and how they react to similar experiences.
18. “Which qualities do you want the most from a partner?”
Summer Stock on Pexels
Everyone has different standards when it comes to relationships. By asking someone about the qualities they want, you can also determine how much they value themselves. At the same time, you’ll know if your qualities match what each other is looking for.
19. “How do you describe love?”
Shamia Casiano on Pexels
We all have different thoughts and views on love and what it should be all about. Since it’s such a simple topic with countless possible answers, you’ll have a lot of things you can talk about on a deeper level because it’s related to emotions and beliefs. That’s why this question shouldn’t be underestimated at all.
20. “Do you believe in romantic soulmates?”
Nikolina on Pexels
When discussing romantic beliefs, the concept of soulmates is hard to miss. Ask them if they’re the kind to believe in fate or other deeply romantic things like being destined lovers. It is a fun conversation and an excellent way to measure how romantic they can be as a lover.