It’s been a long time since I had a good late night conversation with someone. And as someone of the INFJ personality, I especially miss those deep late night conversations. If I can’t go deep with a conversation partner, I tend to bore easily. But with deep conversation, I can go on for hours—especially with someone I like.

If you happen to find yourself talking to your crush late at night, after exhausting your go-to small talk topics, you might start wondering, “What can I do to make the conversation deeper?” Since it’s late and you’re probably a little tired, it can be hard to get those creative juices flowing—unless, of course, that happens to be the time you find yourself at your most creative.

But if you’re looking for some inspiration, here are five deep late night conversation topics you can explore with your crush (or anyone, really).

5 Deep Topics for Late Night Conversations With Your Crush

1. Art

   For me, there’s nothing like art to get a deep conversation going. Talk about a movie/book/song you like and why you like it, and the conversation can go on for some time—especially when you invite your crush to share what they enjoy. Or you can ask your crush about paintings or photos they can’t get enough of, and you can share your own favorites.
   
   You can even look up those photos or listen to those songs while you’re talking or texting if you’re not both familiar with them. And when I say art, that could refer to a famous artist’s creations or it could refer to you or your crush’s art.
   
   You’ll really warm your crush’s heart if you ask them to share their art with you. You could even ask them to text (or email) you samples of drawings or other graphic art they’ve created, or songs they’ve been working on if they’re a musician. But, again, if neither of you is particularly artistic, other people’s art can also make for great conversation.

2. Personality Type

   I’m very fond of discussing personality type as it relates to the MBTI, or the Myers-Briggs Type Indicator. And I know that I will happily discuss it anywhere, anytime. If you or your crush is into the MBTI, you can discuss personality type with them, and that can lead to some deep conversations. You can ask questions like, “What about your type do you relate to the most?” or “What do you feel like people most commonly misunderstand about your type?”
   
   Alternately, if you’re interested but you or your crush doesn’t know their type, why not take a free test during the conversation? This is much more practical for text conversations since you do need time to think about your answers, but you could also make it work with a phone call. And you can also explore other personality tests, like the Enneagram.
   
   You could even just take interesting quizzes online and compare your results. It can be fun to explore your results together and can lead to many deep conversations.

3. The Past

   Sometimes it can be nice to talk about the past with other people. If you want to keep the conversation more on the positive side, you might not want to spend too much time talking about regrets, though, unless you also emphasize what you’ve learned from those experiences. But lessons learned are definitely something you might want to discuss.
   
   You can also reminisce about the past and talk about the things you miss. A nice question here could be, “What do you miss the most about being a kid?” or “What were some of your favorite games when you were younger?” Sometimes it’s nice to remember a different time. And if you and your crush share any of those memories, that can lead to a real bonding experience for the two of you.

4. The Future

   No matter how old you and your crush are, I imagine you’ve spent some time thinking about the future. Maybe you’ve thought about where you want to live or what kind of career you would like to have. Maybe you’ve thought about your dreams and aspirations and the kinds of things you would like to accomplish. And maybe your crush has thought about these things, too.
   
   Why not talk about them together? You could start a conversation like this with something like, “What do you see yourself doing after you graduate from [LEVEL OF SCHOOL]?” or “What’s one big dream you have for your life?” Your crush might find it very thoughtful of you to ask.
   
   But, of course, if you’re going to ask your crush to answer these deep questions, you have to be willing to answer them, too. So, don’t ask any questions you don’t want to answer. That goes for all the items on this list. And even if you ask a question that you’ve never given much thought to, you can go ahead and explore ideas and possibilities with your crush, which will likely deepen your conversation further.

5. Traditional vs. Non-traditional

   If you really want to go deep, why not analyze the most common and conventional ways of doing things, and then contrast that with alternatives? For instance, many people live in typical houses. But other people choose to live in alternative dwellings. Why not try a question like, “What do you think it would be like to live on a boat?” or “Would you ever consider living in a tiny house? Why or why not?”
   
   Any topic where there’s a conventional and an unconventional way of doing things would make for a good subject here. But, to avoid offending your crush, you might want to ask their stance on these topics first. And then, if you choose to take an opposing stance, try to do so as lightly as you can. The ideal, though, would be for neither of you to have a strong opinion either way so you can explore the different perspectives together.

Final Thoughts

Anyone looking to enjoy deeper conversation with their crush would benefit from adding some variety to what they talk about. I hope the topics I’ve just mentioned help serve as inspiration for you. But doing something as seemingly simple as reading more and taking time to reflect on what you’ve read can help you expand your mind and give you more new things to discuss with your crush.

It also helps to explore different topics and consider different ways of doing things. That way, when you talk to your crush late at night, they’ll probably begin to look forward to all the intriguing things you have to say. And then you two will have plenty to talk about for hours.

Now I turn it to you. What conversation topics do you think could lead to deep late night conversations with your crush?

~ Ashley C.

Last updated: January 29, 2024