How to Have a Fun & Effective First Date

Dating Details

First dates can be nerve-wracking. Between choosing the perfect location and wondering if you and your date will click, you may not have thought of things to talk about that go beyond small talk, but it’s a good idea to brainstorm conversation topics that will help you really get to know your date. We asked a couple of local experts why good questions are so important and what they like to ask on a first date.

Sail Past Small Talk

As Anna Reeves McCutcheon at First Things First explains, “If you are someone who dates with a committed relationship in mind, then it’s crucial to suss out compatibility. I treat first dates like an interview, but they can still be a lot of fun!” Open-ended, exploratory questions are key to really getting your date talking compared to questions that can be answered with a simple yes or no. Jenifer Sartain, founder of The Dating Initiative, illustrates the point, saying, “A great question opens the door for your date to share a part of themselves with you. Questions can convey that you value their input, you care about their current state, you want to know more about them, and so much more.”

When you’re planning a first date, you’ll want to have a lot of opportunities for conversation, but there are a couple of ways to go about it. If you’re opting for conversation over a meal, you won’t want to go to a place that’s either too loud or too quiet. Instead, “aim for a restaurant that you know has great acoustics, ideal background noise, and comfortable table spacing,” Sartain explains. 

illustration of a good first date conversation

Or, if you’re more comfortable doing activities while you talk, try taking a walk through a park or along a greenway, she says.

Not sure where to begin? Try out one of these conversation starters on your next date!

Jenifer's Top 3 First Date Questions

  1. “If you could switch jobs with anyone in the world for one day, who/what job would you choose?”

  2. “Someone gives you $500 and tells you that you can’t spend it on bills; you have to get something that’s a want, not a need. What do you get?”

  3. “Describe your ideal day off. Are you sleeping or getting up and moving? What’s for lunch? Relax
    or do something productive?”

Anna Reeves' Top 3 First Date Questions

  1. “If you have an entire Saturday to yourself, what would you do?” This is an excellent question because it tells you so much. This question can give you a good idea if they’re introverted or extroverted, what they value,
    what you have in common, and more.

  2. “What do you want your future home to look like/be like?” This is a fun way of asking the cliché question, “Where do you see yourself in 5-10 years?”

  3. “What are your spiritual beliefs?” This can be daunting, but you’ll want to ask this question if you are a person whose spiritual beliefs are foundational to your life.

Picture of Jenifer Sartain

Jenifer Sartain

Owner & Founder, The Dating Initiative

Picture of Anna Reeves McCutcheon

Anna Reeves McCutcheon

Social Media Manager, First Things First

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