Those initial dates can be so much fun! But they can also be a bit awkward, nerve-racking, and hard to navigate. Let’s talk about what to talk about on the first few dates, so you can get to the good stuff!
Not to set a mediocre bar, but I truly believe those first few dates are all about the happy medium. You’re just trying to figure out if you want to keep seeing each other. You don’t want to waste each other’s time, but you also shouldn’t be trying to figure out if you want to marry him (there’s plenty of time for that girlfriend, chill!).
Trust me, I’ve run the gamut on extremes here, and I can promise you that they’re not serving us in the early stages of dating. When I was younger, I thought I was supposed to know almost immediately if he was “the one.” There were times when I stopped just short of naming our imaginary children. *Facepalm* I’ve also had rounds of dating where I was a bit too indifferent to the process…and accidentally drug it out way longer than necessary.
So, I’m here to equip you with some tools to make the most of those first moments, without all the undue pressure. Spoiler alert: it comes down to conversation. You’ve got to get to talkin’…and maybe get to walkin’. I did a blog post on pacing during the first few dates, you can read it HERE.

I truly believe those first few dates are all about the happy medium. You’re just trying to figure out if you want to keep seeing each other.
But what exactly do you talk about in order to gather some good get-to-know-him info, without seeming like a stage five clinger? I’ve got you covered, darling!
There are three categories that I love to focus on:
1. Passions – What lights him up?
Have you ever asked someone about their idea of the ideal and not seen them immediately illuminate? But seriously, stuff like this is so much fun to talk about! Step outside of the box of day-to-day stuff (ya know, the questions that make you feel like you’re on a job interview), and find out what gets him excited.
This kind of topic really makes your time together fly. Plus, you’ll get a tiny bit of insight into his dreams, what kind of path he might want to take later on, and his outlook on life’s possibilities (I am a diehard optimist, so this is a big one for me!).
Questions:
- What’s something you love that you wish you could do more of?
- If you won the lottery, what cause would you most want to support?
- If you could go do anything for a year, what would it be?

2. Personality – From favorite picks to problem-solving!
Time to learn a little about what he likes! Not because you need to like the same things, but because it will help you get an idea of what he really is like as a person. Here we’re finding out where ideality meets reality for him. You can also get a feel for how he handles certain things (like being less than stellar at something). But, be sure to keep it light!
Questions:
- If you could only re-read one book and re-watch one movie in your life, which ones are you choosing?
- What’s something you’re terrible at? This one gives you a bit of insight into his self-awareness and humility. (Spoiler: NOBODY is bad at nothing, sooo….)
- You have a totally free weekend, what are you doing with it? This is such a great indicator of how he likes to spend his time.

3. Purpose – What does he value?
This is my kind of third date territory. As you know, I have a three-date rule that I actively implement, so sometimes that means the third date is how I decide if I would like to keep seeing this person, or if it’s been a good run. Time to find out what matters to him…
Questions:
- Who is someone you really admire and why?
- How would your closest friends describe you? The perfect question for a healthy kind of humble brag. You’re not asking him to describe himself exactly…you’re asking him to convey what his best buds would say!
- What’s been your favorite part about your career? This question ends up being less about what he does and more about why he does it… or maybe why he might want to go do something else!
Hope this helps you have a great game plan for what to talk about on the first few dates. Here’s to getting to the good stuff, darling!
