First Date 101: Conversation Do’s, Don’ts, and Tips

In our most recent First Date 101 article, we started talking about Conversation. Having good conversation is obviously crucial to having successful first dates. In that article, we talked about the goals of conversation–more general theory of how you should be conversing. In this article, we’re going to get more concrete and give actual directly actionable advice: conversation do’s, don’ts and other tips.


Ask open ended questions

It’s a common mistake to think that asking questions gives a date an interview vibe– that’s only true if you ask boring one word answer questions. Open ended questions are a core part of engaging conversation. By asking an open ended question, you give your date an opportunity to take the conversation in a direction that’s interesting to them–which will make them more engaged and enjoy themselves more, because let’s face it, everyone likes talking about what they want to talk about!

A great open ended question I like to use is the “story question”, it takes the form: “Do you have any good [xyz] stories? Fill in xyz with one of many options. For example, any good online dating stories? Any good stories from your last trip? Any good celebrity stories? The options are quite, no pun intended, open ended.

Other simple open ended questions include:

How did you settle on [neighborhood where she lives]?

What made you get into [hobby] ?

Ask follow up questions

Another way to keep conversation flowing on the same vein as open ended questions without the challenge of finding a good open ended question is follow up questions. For example: Have you ever traveled to Asia? Yes. Where did you go? What was your favorite? However, be careful taking this too far. A string of follow ups can start taking the form of an interview if they are easy to answer in a simple format.

Change topics of conversation

A common mistake we hinted at in our last First Date 101 piece is conversation topic switches. Do not be afraid to change the topic of conversation, even if it seems abrupt. It’s a big mistake to stay on the path of an uninspiring topic just for the sake of conversational continuity. Getting into engaging conversation is much more important than smooth conversation transitions.

For example: if you suspect you are both foodies, but you’re talking about work and neither of you seem particularly excited about it, switch gears. Ask her about her favorite cuisine. Just change the topic.

Subtle compliments

You’re on a date, so it’s ok to flirt and show interest. Showering your date with compliments is typically a mistake, but subtle compliments or one liners that compliment her are hugely valuable and will likely make her open up a bit more. A few examples:
If she went to a good school — throw in a “and she’s smart too, nice!

If she has a unique skill or is very talented at a certain thing — fire off an “impressive, I’m jealous!
You can always use this to segue into talking about something you’re good at. For example, if she’s a talented artist and you aren’t good at art but you’re a good musician, you can say something like: “Wow that’s impressive, I wish I was good at art, music I can do, but sadly, not art” — it will almost always prompt a shift in the conversation to her asking you about your music.

Listen and show you listen

One of the most important things during conversation is knowing when not to talk. When she’s in a groove, listen, and demonstrate you are listening by asking relevant questions. Most women will talk about things they want to talk about, and will enjoy talking about it. Keeping them talking about a subject they’re passionate about will make them enjoy talking to you more. The best way to do that is to simply listen.


Avoid overly sexual innuendo

Some flirtation and occasional injections of sexual innuendo are fine, but avoid going overboard. There’s a fine line between being sexy and being a creepy pervert. If you’re an expert dater, you can safely ignore this advice, but this is our First Date 101 guide, and if you’re at the ‘101’ level, sexual innuendo done wrong can be disastrous.

Avoid religion and politics

The old wives tale is true–even given the current political climate, perhaps especially given the political climate, it’s best to avoid political conversation as best you can–even if you agree. Religion is the same. If religion comes up, bring up your observance level and religion but try to keep the conversation to that and nothing more.

There are a few other topics that most recommend avoiding on a first date, such as ex’es and money. We don’t think that’s necessarily as important as avoiding religion and politics. If you’ve had a serious girlfriend, it’s only natural that they were a large part of your life. It’s difficult to completely not talk about a large part of your life, nor have we ever noticed it’s a big turn off, unless you literally can’t stop talking about them.

Don’t Interrupt 

It seems obvious, but on a first date, the adrenaline is pumping and it’s sometimes hard to remember our manners. Have “don’t interrupt” in the back of your mind–this will help avoid interrupting her. If you do interrupt in an awkward way, simply apologize and tell her to keep going.

Don’t stay on “bad” topics

If you two are on a topic that makes you (or her) uncomfortable, is dull, or isn’t a topic you really know much about so you’re looking out of your depth, switch the topic. Don’t stay on topics that aren’t conducive to you looking better in the eyes of your date and her having a good time.

Tips, Tricks and Hacks

In addition to the basic Do’s and Don’ts covered above, there are a few good tips, tricks, and “hacks” you might want to keep in your back pocket.

1. Awkward Silence Busters:

a. Go to the bathroom to avoid awkward silences

It goes without saying that awkward silences on a first date are well, awkward. If you’re both running out of things to say on the current topic, and you sense an awkward silence is coming, break it up with a bathroom break. Obviously, you can’t do this all the time, but it’s a great way to avoid an awkward silence. Go use the facilities, and at the same time, regroup and figure out a topic to talk about on the way back.

b. Order another round / get a water

It’s the same concept as the bathroom break–awkward silences, or “almost awkward silences” are great times to order another round, (or get each of you a glass of water), or pretty much do anything that avoids sitting there not talking.

c. Prepare “emergency” topics in advance

If you worry about awkward silences, and for one reason or another the tips above do not apply (you just went to the bathroom 15 minutes ago, for example), have a couple topics handy. Remember, switching topics  abruptly is fine for the most part. 

2.  People watch topics

Another tip if you’re running out of things to talk about, or simply need to change the topic, is to make a comment about someone or some thing at the bar. Don’t insult or be rude, just a simple observation that can lead to talking points. For example, say you see a couple at the bar, ask your date: “What do you think, first date?”

3. Ease in abrupt topic changes

Our favorite way to ease in a very abrupt topic change is to say something like: “Funny, I just remembered…“. Other good segues for particularly abrupt topic changes might be: “This is random but…” or “Oh, by the way“.

Once you’ve gotten her out on a date, you’ll want to keep her interested, and make her more interested. You can do this first and foremost with conversation. These tips should help you do both.

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