What to Talk About on a First Date

You asked her to meet in person...she said yes.  Sweet success!  

First, congratulate yourself.  You fought the good fight to get here: you made an effort to write a great first message, took the time to write an online dating profile that stands out, and stayed vigilant about keeping your conversation engaging, thoughtful, and fun (for both of you).  You deserve this win.

Now, we’re on new terrain.  The first date.  It’s a brave new world and it’s hard to know what to expect.  Some details you can plan ahead for, like the place you’re meeting.  What you can’t plan for is what it’ll actually be like to meet her, talk to her, and connect with her.

There ARE a few critical tools you can prepare yourself with to help a date go smoothly: conversation topics, conversation skills, and how to read and adapt to nonverbal cues.  

Here’s what you can do:

1. Prepare Yourself with Conversation Topics

Start by quickly re-reading a girl’s online dating profile and the messages you’ve exchanged before your date.  (This is especially important if you’ve been talking to more than one girl!)  

This will remind you of what you already talked about and give you a couple follow up questions to ask.  These are safe conversation topics to have in your back pocket, because you already know how you connect in these areas.  It’s good to bring these up again on a first date when you want to take the conversation to familiar ground, to make her (or you!) feel comfortable.

Bonus: reviewing what you’ve already talked about saves you from accidentally asking her the same questions again -- making it seem like you don’t care about her enough to remember what you’ve already talked about!  

Reviewing your previous conversations and her profile can also inspire a couple new topics to introduce if you get tongue-tied.  A girl’s profile is basically a list of things she’s interested in talking about.  Use it to your advantage!

Why else is this first step critical?  When a guy shows up prepared with stuff to talk about, it’s kinda old-school and really smoking hot.

2. Hone Your Conversation Skills

At one point or another, everyone’s arrived at a date and realized that they have NO CLUE what to talk about. This happens to girls just as often as it happens to guys!  Plus, online dating can add that extra level of weirdness. 

Here are a few tricks to spark conversation and hold her attention when you’re drawing a blank:

A. Focus on Your Common Interests.

Use your prep work from item 1.  Check out your date’s profile and create a mental list of hobbies or interests you have in common. On the date, ask her about those things!

You can ask her really specific questions, like about books you both like or TV shows you’re both into.  

For example: “You said you like Master of None.  I do too!  Did you know those were Aziz's real parents?”

Or you can ask her more open-ended questions to get her talking, reveal more of her personality, and show how she thinks.  

For example: “That’s cool you’re into Sherlock, too.  What do you like about the show?”

When you do get her talking, go ahead and weigh in with your own thoughts, opinions, and excitement for the hobby or interest you share.  You want her to learn about your personality and how you think, too!

B. Don't be Afraid of the Things You Don’t Have in Common.

There’s nothing creepier than a date who agrees with everything I say.  It feels like he’s desperate for me to like him at all costs.  Yeesh.  Meanwhile, a little friendly debate is a great way to spice up a date!  It’s OK to point out things you don’t have in common, too.

For example: “Seems like you’re a big Kanye fan. His latest album didn’t do anything for me. Do you see something I’m missing in his newer stuff that might change my mind?”

As long as a guy is asking our opinion and not diminishing our thoughts or antagonizing us, girls are OK with a friendly disagreement on a date.  This is a natural part of getting to know someone.  A little difference of opinion can create a fun spark in the conversation!

C. Ask Questions that are a Little Personal.

On an online dating first date, lots of guys make the mistake of asking the same old questions that don’t give a girl a chance to reveal her originality. Girls get bored by guys who ask her to list off facts about our lives, like:

- What part of town do you live in?
- What do you do for work?
- How long have you lived here?
- What did you do last weekend?

A girl’s answers to questions like these don’t share much about who she is and what makes her that way.  On the flip side, it’s not hard to turn these into questions that DO ask about her life, beliefs, thoughts, and feelings.  For example:

- What’s your favorite thing about living in that neighborhood?
- How did you get into web development?  What do you like about it?
- What brought you to the area?
- What kinds of things do you like to do on the weekend?  Why?

D. Ask Unique Questions.

When the conversation gets rolling, it’s fun to go beyond the basics and ask questions that bring out what makes each of you unique. Here are a few examples:

- Who would you invite to your ideal dinner party?
- What does success mean to you?
- Have you ever sent an embarrassing email?
- If you had tomorrow off work, and could literally do anything, what would you do?
- Do you vote in elections?
- What was the last guilty purchase you made?

You can also take a look at the questions on her OkCupid profile, like, “Would you rather that only good things or interesting things happened to you?” Which of those would be fun to ask her about?  

When she lights up and the conversation is flowing, enjoy yourself and share your own thoughts! This is the holy grail of a date -- when you’re having fun, opening up, learning about each other, and not worrying too much about asking the “right” questions.

E. Keep the Conversation Going.

Keeping the conversation going in a natural way makes a date flow smoothly.  It’s fair for each person to hold up their end of the conversation, but sometimes one party needs a little more help.  It’s impressive when a guy can step in and save an awkward silence.

Here are some simple ways to ramp up the conversation longevity:

  • Ask follow-up questions. Get your date to share more about herself by asking her to elaborate on her opinions, her interests, and her life.  Asking questions that begin with “Why,” “What,” and “How” prompt her to respond with more than a “yes/no” answer!

  • When she asks you questions, respond and then relate your answers back to her. For example, you can say, “What do you think?” or “How about you?” or “What would you do if you were in a similar situation?”

  • Be curious and show her you care about her thoughts. Your date will immediately find you more interesting if you show interest in her. Just like the adage that “boring people are boring,” when you’re on a date, engaged guys are more engaging. When she shares a detail with you, show real interest in it!  

For example: “Wow! I’ve always wanted to visit the Grand Canyon. Was backpacking cold in February? How much water did you have to bring for three days?”

Every now and then we encounter a date that just gets stuck, no matter how hard you’re working to keep things going smoothly.  If you’re only halfway done your beer, and she’s across the table, silent, fumbling with her zipper, turn your attention to nonverbal cues to get things back on track:

3. Pay Attention to Nonverbal Cues

Beyond the words we speak, we convey meaning in the way we listen, the tone of our voices, and the way we sit.  When a guy is aware of these nuances in conversation and can adapt accordingly, it’s a pleasure to be in the company of his great social skills!

A. DO Listen

We’ve all seen it happen.  There's a couple at a restaurant or a party: one person is non-stop talking, talking, talking...with no awareness that the other is totally bored, politely nodding, or glancing around the bar for an escape plan.

It’s good to check in with yourself on a date.  Lots of us ramble when we’re nervous or trying to make a good impression.  It's easy to slip into this mode, but it's not the smartest strategy.  

When you ask her questions and prompt her to talk more, you show her that you're interested in her.  This is flattering.  You also get to learn more about her (which serves you well), and it makes you a fun, engaging person to talk to -- an important quality in a potential boyfriend!  

Being a good listener takes practice.  If you know you have a tendency to talk a lot, simply try to listen twice as long as you talk.

B. DON’T Interrupt

When she’s talking about something you’re excited about, or have a strong opinion about, it’s easy to accidentally jump in and interrupt.  If this happens once or twice it’s OK.  When a guy constantly interrupts, it’s really rude.  It makes us feel like he doesn’t value what we have to say -- that he thinks his own thoughts are more important than everyone else’s.  

Hear her out before chiming in.

Conversely, a bit of silence in between responses is OK too.  You’re allowed to take some time to consider what she’s saying, or what you want to say next, before responding.  Being thoughtful and conscientious are great qualities!

C. DO Pay Attention to Posture

Sometimes we convey as much with our bodies as we do with our words.  Body language is a good clue in the context of the conversation.  For example:

She’s leaning toward you → This indicates she’s probably engaged in the conversation and she’s taking you in.

She moves her chair or body away from you → She’s probably establishing a boundary she’d like you to respect, or wants to distance herself from what is being said or conveyed.

While paying attention to her posture, you can make yourself more approachable by being aware of your own. Consider the following:

Folded arms → This usually conveys that you’re protecting yourself, or that you’re closed off.

Sitting up straight, or forward in your chair → You’re alert and engaged.    

Leaning back in your chair → You’re unengaged and not interested in the conversation.

D. DO Pay Attention to How Quickly She’s Eating or Drinking

A huge part of what makes a relationship successful is the ability of two people to work well together. On a first date, this means being able to read each other’s energy and respond to it.

If you realize that your date is nervous, that’s an opportunity for you to work with her to lighten the mood. If you realize that she’s confident and relaxed, that’s an opportunity for you to enjoy connecting with her as the conversation gets more personal.

Here are some clues that may indicate her energy level:

Quickly drinking or eating →  She may be trying to rush through a date, or is nervous and uncomfortable.

Slowly drinking or eating →  If your date is relishing her food or beverage, she’s taking in the experience of meeting you fully. When you observe her peaceful demeanor, use it as a clue that you can enjoy her presence too. Relax. Take in the moment. Be you.

Fidgeting → If she’s fidgeting or tapping her foot, this may be an indication that she’s anxious. You could experiment with a few different ways to make her feel more comfortable.

Here are some ways you can try to lighten the mood:

- Tell a story about something embarrassing that happened to you.
- Observe someone in the establishment doing something funny and point it out to her.
- Ask her about something easy to talk about, like food! What’s her favorite recipe?
- Ask her about one of those “safe topics” you already discussed in your messages together.  Build off of that so she feels like she’s on solid ground again.

When you find one that works, keep that energy going.  Chemistry and connection are the best possible outcomes from an online dating first meeting!  Enjoy it!

Observe & Enjoy

From preparing for what to talk about on a first date, to engaging a girl in conversation, to reading her nonverbal cues, there’s a lot that goes into that first meeting in person! While you can’t plan for everything, you CAN increase your chances of connecting with a girl by paying attention to the details. Be true to yourself, but also hone these skills to help yourself find someone you enjoy being around, who also enjoys being around you -- for many more dates to come!

READ MORE Tips for Meeting in Person


Can't get to the date because you can't get any message replies?  Let me know.  I’ll review 5 recent messages you’ve sent, point out what you're doing right, show you what's hurting your game (and why!), and give you specific pointers for how to improve your response rate -- so you can get to the dating part of online dating!