How to Spark a Meaningful Conversation on a First Date

Stave off awkward silences with these conversation tips.
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Monica Gabriel Marshall
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Stave off awkward silences with these conversation tips.

For many people, first dates are painful. Where do I even start with this, well, complete stranger? we might ask. We have mutual friends, but that will only get us so far. Questions about family can seem like a land mine for too personal too soon. Work? I dont want our date to sound like a quarterly review!

Knowing what questions are most likely to lead to meaningful conversation on a date can be stressful. But asking the right questions on a first date is not rocket science. We don’t really need a list prepared ahead of time; in fact, it might make things more difficult for you if you do. My theory is that when we are too consumed about knowing whether or not this guy is “the one” and making a good impression rather than actually getting to know him, our nerves make it hard to make natural conversation.

So, instead of giving you a list of dos and don’ts, here are some tips to help you get past those first-date nerves and on to meaningful conversation.

Worried that this date will be a waste of time?

I would wager that most of us wouldn’t have so much anxiety about getting to know a new friend. Why? Because we are not concerned that if things don’t “work out,” this lunch will be a total waste of time. We just don’t think like that when we are getting to know a new person in a platonic sense. I would argue that we shouldn’t think that way when we are getting to know someone in the romantic sense either.

Now, I know what you are thinking, but I am so tired of first dates that go nowhere, and I get it. I have been there, too. But think of it this way, a girl’s gotta eat, so it’s not really a waste of time to block off an hour or two for dinner, and you get the added bonus of sharing it with someone new—instead of your TV. All things considered, not really a waste of your time.

Focus on putting him at ease. 

The two best pieces of advice my older sister gave me about dating are (1) dress up and act casual, and (2) focus on putting him at ease. The first piece of advice is tangential to this conversation, but valuable all the same, so I will quickly explain: If you are stressing about what to wear for a first date, opt for the dressier option, and be as approachable as possible.

The second piece of advice relates to the dilemma of finding good questions to ask a guy on a first date. “Focus on putting him at ease” rather than worry about how you are coming across. Assume that he is nervous as hell, even if he isn’t acting like it. Your job then is to help him get comfortable by inviting him out of himself a bit with conversation.

When you are focused on putting your date at ease, you won’t be as worried about what to ask; you will naturally go for conversation starters that will make him smile and feel good about himself. “This restaurant has a great atmosphere. Nice choice! Have you eaten here before?” It doesn’t have to be questions either; making your date comfortable might also mean simply being warm and inviting by offering a little bit about yourself. “My family used to come here every Christmas to ice skate and have hot chocolate; it is one of my favorite childhood memories.” See what we just did there? That was an invitation for him to ask you more about growing up and lets him know that you would be happy to open up to him. What a relief for your poor nervous date!

But I can’t stand small talk! 

Icebreakers aside, I dread a night of surface-level conversation that requires the perception level of Sherlock Holmes to learn anything meaningful about the other person. Ah, yes, I see his shirt is haphazardly tucked into his pants, which means he was in a rush, which means he probably works late hours . . .

To be sure, on a good first date you should come away with a deeper understanding of who the other person is than when you first met. But stressing about all the information boxes you need to check by the end of the date is a recipe for disaster. The only thing you need to know about this guy after the first date is whether you want to go on a second one.

On the first date, you don’t need to go to deep and probing places nor should you feel the need to keep things surface level just because you don’t know what the boundaries are. Conversations should deepen organically, especially if both people are comfortable and interested in getting to know each other. Conversations about family, faith, and future don’t have to be restricted territory; they can be as light or deep as you both choose to take it.

What begins as a question about where he was raised might turn into a discussion about public versus private education. You may not know if he has a good relationship with his mom yet, but that’s OK because you are still learning something about him. This is a good start.

The key is to ask questions that allow your date to tell you as much or as little as he is comfortable with. A good rule of thumb is to keep conversation-starting questions broad and conversation-developing questions more specific. For example, “Do you have family in the area?” From here your date can answer your question and take it in any direction he chooses. “No, but my sister and her family live five hours away, so I see her a little more frequently than my mom and dad in Los Angeles.” Then you can take it a little deeper. “Oh, that’s nice! Are you and your sister pretty close?” Remember, the first date is just the first step in becoming more familiar with this person.

Ask questions you want to know the answers to.

Just because you don’t have a list of questions handy on a first date doesn’t mean that you shouldn’t be thoughtful about your questions. There are three secrets to a well-placed question. Keep these front of mind, and navigating the “getting to know you” stage will be enjoyable for both you and your date.

1. What do I want to know? Being the first person to pop a question is always a bit of a Hail Mary. But if you are throwing one out there, be sure to make it a question you actually want to know the answer to. A good conversationalist will answer your question and elaborate a little, giving you bread crumbs to follow up with a second question if he doesn’t automatically reciprocate.

Once you get past preliminaries, pick any question that might help you find out something you want to know about him. I’m always eager to find out about a person’s family, so I always ask about that first. “How many siblings do you have?” or “Where did you grow up?” are good places to start. Listen to his response, and ask him whatever natural follow-up you might be curious about. Hopefully, your date will ask you a few questions in return. If not, don’t hesitate to volunteer information—he might be nervous and may need a hand.

2. What do I want him to know about me? If you do not want to talk about work, don’t ask him about work. The one who asks the first question gets to steer the conversation, so pick a question you would like to answer as well. My family and my work are two things I feel very proud of; I light up when I talk about either of them. So, if it’s up to me to get the conversation going, I’ll head in either of those directions. I don’t love to talk about my college experience on a first date, so I never lead with, “Where did you study for undergrad?”

3. What does he want to talk about? Once you hit on a topic that gets your date going, don’t put on the brakes just because you are anxious that you’re not covering enough ground. It can be really fun to spend time on one subject, and my bet is that you will learn more about what makes him tick from this one topic than if you were to squeeze in all of your “Top Ten Make It or Break It” questions. If you ask him about work, don’t hesitate to ask him something like, “Do you enjoy it?” and follow up with, “What do you enjoy about it?” This will give him the opportunity to break away from the topic of work if he isn’t excited about it and the ability to tell you about something he does enjoy instead.

Don’t head into a first date feeling the pressure to “make” conversation or find out if he is the one. They say that you meet your future spouse “when you least expect it.” Maybe this just means that when you stop worrying about asking the right questions, you might find yourself having a really great time . . . and then a really great time on the date after that . . . and the date after that . . . and, well, you get where I’m going with this.

Photo Credit: Manchik Photography