Dear Dr. Chani,

I find myself stuck in a recurring situation on my first dates, and I am not sure how to break free. Despite my best efforts, my conversations tend to be awkward, superficial, and ultimately lead to the dreaded dead end. I consider myself interesting and I do not have a problem making conversation with my friends, yet when I am face-to-face with someone new, I somehow default to safe, typical topics that end up even boring me!

I got some advice that before every date, I should prepare a mental list of topics to talk about and stories to share but the discussion often seems repetitive and insignificant. I have even tried asking open-ended questions like “What do you enjoy doing?” or “What is your family like?” only to receive short, perfunctory responses that rarely spark further conversation. I am wondering if my approach is simply too reserved or if I am unintentionally sabotaging my conversations.

It is not surprising that girls often give me feedback that even though I seem like a nice guy, they “don’t see it going anywhere” or they “don’t think our personalities are a good fit.” It is really disappointing because if I could get past this conversation issue, I really think that my personality would shine.

At this point, I am anxious every time I go out on a first date that my conversation will not be able to get past the initial superficial chit chat. I find it so uncomfortable when my conversations hit a point of silence that lingers until I find something new to talk about.

How would you suggest that I steer a first-date conversation into a more meaningful conversation without coming on too strong or forcing vulnerability too soon? Should I be more self-disclosing on a first date or is there a more subtle way to shift from small talk to deeper conversations? I look forward to getting your insights and advice on conversation techniques that could help me create a natural flow of interesting and meaningful conversation.

Sincerely,
Ralph

Dear Ralph,

Your description of how difficult it can be to make meaningful conversation on a first date is very real and it is something that I find a lot of people can relate to. You are not alone here. First dates can be awkward, and it can feel frustrating when conversations do not flow the way you had hoped. It is completely understandable to rely on safe, familiar topics when you are nervous, but when those exchanges stay superficial and do not spark real connection, it can feel discouraging. The fact that you are asking this question shows that you genuinely care about making meaningful conversations happen—and that is already a great starting point.

One of the reasons why people tend to find their conversations dry and dull is that they stick to facts and do not get deeper. For example, when you ask questions like “What do you enjoy doing?” or “What is your family like?”—it can lead to quick, factual answers such as “I like exercising,” or “I have three siblings and they are doing x, y, and z.” Sometimes, it can be hard to know where to go next in a conversation about facts.That is often when a conversion hits a dead end, and you need to scramble to find something new to talk about.

A key to unlock a more satisfying conversation is to reach for the feelings. For example, you can ask follow-up questions such as, “What about exercising do you enjoy?” or “Which sibling do you feel closest to … why?” Listen closely to her answers, and let her know that you understand what she is talking about.

Framing questions creatively can also make a big difference. Instead of asking, “What do you do for fun?” you might say, “What is something you are really passionate about that most people would not know?” or “What was one of the highlights of your week?” These kinds of questions spark richer conversations because they move beyond surface-level facts into feelings, experiences, and perspectives.

Another effective strategy is active listening and curiosity. If your date shares something—no matter how small—lean into it. Instead of moving to the next question, ask follow-ups that show genuine interest: “What was your favorite part about that?” or “How did that make you feel?” People love to be heard, and when they see that you are listening closely and responding thoughtfully, they are more likely to open up.

You can also take the conversation deeper by building a little personal storytelling into your conversation. For example, you can share a funny story that happened recently to you at work, an interesting case that you are working on, or explain what motivated you to choose your profession. In another example, if the topic of travel comes up, instead of just mentioning places you traveled to, share an experience that made an impact on you—an unexpected adventure, a funny mishap or a meaningful experience that changed your perspective. This invites your date to respond with her own story, which makes the conversation more natural and engaging.

It is also helpful to embrace a bit of vulnerability. You do not have to spill your life story right away, but expressing your own thoughts and feelings—even in small ways—can set the tone for a more open exchange. For example, if you are unsure how to navigate to where you are going on a date—make a lighthearted comment about your unfamiliarity with the directions. If something funny happened to you earlier that day, share it. Little moments of openness help break the tension and make the conversation feel less like an interview and more like two people genuinely getting to know each other.

And remember—it is OK to have pauses. Silence does not always mean the conversation is failing; sometimes it is a natural part of reflecting on what has been said. The way you feel about silent moments often becomes a self-fulfilling prophecy. If you view them as awkward—so they will be. Yet, if you take them in stride and see them as a breather in the conversation and something that happens when two people are comfortable with each other—it will feel more natural. Instead of rushing to fill every gap, embrace those moments and see where the conversation naturally leads.

You do not have to wait until your next date to practice these skills. Try striking up a conversation and developing it with one or two new people every day. This will help you get used to developing a meaningful conversation and will hopefully reduce your anxiety before you go out on your next date.

I hope these ideas make your next first date feel a little more effortless and enjoyable. You are already on the right track—just a few small shifts can make all the difference. Keep experimenting, stay curious, and most importantly, have fun getting to know new people!

Wishing you much success,

Chani

Dr. Chani Maybruch is a social psychologist who has specialized in helping people build and enhance their relationships for over two decades. If you would like to improve your personal and professional relationships, reach out to her at chanimaybruch.com.