6 First Date Conversation Starters

Contributing Editor, Stephanie DeLacy chats all about how to bring killer conversation and zap any awkward silences on your next first date.

There is no doubt that dates are awkward. But there are a few ways to minimize the awkwardness, get to know your date, and help you both have a great time.

One of those ways is to ask the right questions. Asking your date the right questions can open up your discussion and lead the two of you to get in lost in conversation, which is always a win on a first date.

A few things before we dive in. Questions on a first date are not interview questions. Yes, they are helpful tools to get to know the person on the other side of the table, but they are not about investigating them or evaluating your compatibility. They are only about getting to know the other person.

It should never feel like you’re grilling your date or that one person is asking all the questions and the other is doing all the answering. Your questions should lead to conversations where you’re both chiming in.

You shouldn’t even think of these as questions, but rather, conversation starters.

With that being said, it’s important to note that you should only ask questions you feel comfortable asking as well.

Who is the most famous person you’ve ever met?

This is a nice soft question that almost always generates a fun response and discussion. Of course, there’s always the risk your date has not met anyone famous but I’ve been asking this question to all sorts of people for years, and I always have the most boring response – I shook Rahm Emanuel’s hand during the Renegade Craft Fair while he was running for mayor. And I still believe this is the most fun question to ask.

Your date might respond with a niche celebrity that you might not recognize, like a pro skateboarder or an author at a book signing. Use this as an opportunity to learn more about your date and his/her interests.

What destinations are on your bucket list?

Admittedly, this is my least original question on this list but I included it for a few reasons. First, because everyone loves to travel. Even those of us who aren’t well traveled, we all have a dream vacation. So, while it’s not the most creative question, there’s little chance your date will shrug their shoulders and say “IDK”.

I also think this question deserves to be on this list because it can open up your conversation so much. Because you don’t just have to stop at their top cities they want to visit, you can also ask how they like to travel – do they like to stay on resorts or visit cities? Do they like to have a plan or fly by the seat of their pants?

Lastly, this question will allow both of you to swap fun, crazy travel stories, which is always a good time.

How did you end up in [your city]?

I love hearing people’s stories about how they came to live where they do. Was it for a job? Was it a lifelong dream? Have they lived here their whole life? Whatever the reasons are, their story can tell you a lot about what they like (and don’t like) about your city.

What are you passionate about?

This is a version of a question that we tend to ask already but I like the phrasing of this question a lot. Don’t ask what they are most passionate about. Open it up way more than that. This is a broad enough question that your date should feel free to tell you about their work, family, side-hustle, hobbies, and more, which will get you two talking about anything and everything.

 Tell me about your best day at work.

Of course, you’re going to ask what they do (or you might already know), but I like this question, especially when I don’t totally understand what my date does for work (like, anything to do with engineering). Instead of having them start from scratch explaining the nuances of their job, asking them about the best day is an easy way for them to verbally illustrate what they do.

I find it very attractive in a partner when they are passionate about what they do for a living so this question can be a great way to get both of you talking about your jobs and exposing your passions.

When is the last time you were a sloth all day?

I love this question; it’s a fun way to get a little vulnerable with a first date. We typically like to show our best selves on first dates and we don’t talk about how we spent the last two days watching Tiger King TWICE, like I just did. But if someone is feeling comfortable and doesn’t mind making fun of themselves, this is a fun question that will usually make both parties chuckle and will probably lead to a lengthy discussion about binge worthy shows.