This article discusses my general approach for first date conversations with online dating. If you’re instead looking for a list ideas, check out my article on First Date Questions and Conversation Starters.

For all my shyness, I never found it very difficult to have conversations on a first date. It isn’t that I gained confidence, I just planned ahead.

First, as mentioned previously, I intentionally kept first dates short and only extended the “good” ones. Second, I would memorize topics that I could talk about. These two approaches worked very well together ensuring that (at least on first dates) there were never any awkward pauses.

starting first date conversations
Photo by liquene
The topics you choose should not solely be there to fill in empty space. You know qualities you are hoping to find in someone else and many of your topics should be used to discover if your date has these qualities. At the same time, you can’t put your date “on trial” so you need to mix your conversations up between discovery, simple light-hearted small-talk, and sharing about yourself.

Above all, you should be listening! Hopefully that goes without saying. I’ll break down the first date conversations into three categories and discuss each. However, any good date won’t require as much thinking as this information suggests. Just be familiar with what you want to know and what you want to share. If there is a connection, things will fall together on their own.


This refers to parts of your conversation where you are discovering if who you have just met has what you are looking for. This is important to mention because you are looking for particular qualities whether you’ve admitted it or not. Early on, there may not be much you care to discover; this was the case for me. However, the more I dated, the more qualities I identified as something I desired.

Be patient when trying to learn about the person you are dating. Don’t turn a fun evening into an interview. If your date resists at answering some questions, just leave them unanswered and move on to lighter conversation. The only reason to learn everything about your date right away is if you are assuming there is only going to be one date, in which case there is no point in learning anything about them at all!


It is important to be able to have light-hearted conversations to prevent your date from becoming too impersonal. You should have fun talking with your date…even if that means intentionally planning on talking about some of these areas. In many cases, the small-talk will come naturally but there’s nothing wrong with being prepared.

Online Dating Experiences

It’s up to you what you want to talk about but I would recommend being open to discussing your online dating experiences. I found this made for excellent small-talk and I also found that once I started, my dates had stories that they were excited to share.

There were frequently “My dates have been worse than yours” competitions that were both friendly and fun. Just be careful not to turn fun conversation into a complaint-fest. Start doing that and your date may be talking about YOU the next time she’s discussing her worst online dates.

You may not have any interesting stories but that doesn’t make discussing online dating a bad idea. I went so far as to share the horror stories that women shared with me on later dates. For example, even if I didn’t have a good story to share I could still counter one of their horror date stories with one that a previous date had shared with me. “That’s nothing”, I would say, “one girl I met recently had been called by a guy she had just met three times before she even got home!”. No one ever took offense that I was sharing others’ stories: the truth is, everyone, myself included, just loves to hear that they’re not the only ones struggling.

Also, I would ask general questions like how long she had been online dating, if she had any success, if she gets a lot of contacts, and other non-intrusive conversations. Aside from making excellent small-talk, these conversations also humanize you. You’re no longer some (potentially weird) person they have just met. You’re another person trying, just like they are, and finding things can be more difficult than anticipated.

Take Advantage of Their Profile

Aside from the fun of discussing online dating, using their profile to fuel other small-talk is a great idea. Favorite television shows, hobbies, professions and most other specifics provided in the profile are excellent topics because, chances are, she will want to talk about these things.

I would also recommend keeping up on current events (even though I found most of my dates weren’t doing the same) and finding some other light-hearted conversation fodder. One example for me was a study about dating. I live in Pittsburgh and at the time my city had been voted the worst city for singles. This conversation always resulted in good discussion on my dates.

Don’t Take Yourself Too Seriously

A final good small-talk topic I found was telling self-deprecating, but funny, stories. These types of conversations managed to turn a few uncomfortable dates into comfortable, or at least bearable, ones. For example, on some dates I would bring up favorite vacations and talk about a road trip I had taken with friends.

I had it in my head that I could drive to Myrtle Beach from Pittsburgh in one shot – even after a work day. While I did make it, I was so tired I parked in a parking lot to sleep. It was raining but was also hot so for the next few hours everyone in the car was fighting over being hot or being wet.

While this isn’t a laugh-out-loud story, this type of conversation helped smooth out more than a few bumpy first-date conversations. I believe that a willingness to share some potentially embarrassing personal stories can bring a conversation from formal to casual. These stories also show that you don’t take yourself too seriously (and hopefully you don’t).


It is important to share with your date the things that you feel make you who you are. Anything that you would be unwilling to change about yourself but that you worry a mate may wish to change is a good candidate for sharing. Some topics, such as a love of travel, are very easy to bring up. Others, like a desire to move in a few years, are more difficult to just come out and discuss.

One way I found to lead the conversation to these topics is to simply ask the question you want to answer. Once your date has answered the question just stop controlling the conversation – that is, stop talking. Most of the time, they will ask you what you just asked them when they’re done answering. Many people will see right through this (I was called out on it several times) but I never met anyone offended by the tactic. If anything, my dates seemed amused.

On a good day, your date will be putting in effort to find out who you are, so this tactic will hopefully be rarely needed. On the other hand, if halfway through your date you realize you’ve shared nothing about yourself, this may be a red flag that your date isn’t very interested in you! The one thing your date may like about you is that you give them a chance to talk about themselves!

A good conversation should be healthy amounts of both sharing and questioning. Don’t feel like you need to explain in full who you are on your first date, though. It is okay to leave a little mystery about who you are. In my experience those dates who seemed desperate to share as much as possible on the first date shared far too much.

Developing A Script

Chances are you’ll never be on a date where you can plan out the conversation in any large part. Still, it’s a good idea to create a mental list of topics to cover.

The dreaded “uncomfortable silence” that can happen on any date doesn’t normally kill the date. However, if these silences come too early or too often they can make both daters very uncomfortable.

Below is an example script close to what I had mentally prepared when I was dating. These were items I would keep in mind to keep the conversation moving if it wasn’t taking on a life of its own.

  1. Initial meeting and introductions
  2. Discuss success/failures of online dating (small-talk)
  3. Is she a family-type person? (Discovery. Sharing if she returns the question)
  4. Work life (Discovery/Sharing)
  5. Entertainment small-talk (usually good topics are easily identified in the profile)
  6. Current events (Discovery disguised as small-talk. I looked for someone intelligent and who cared about current events)
  7. Vacations (Sharing – I went on several road trips that made for great topics)
  8. Goals (Discovery – careful with this topic. Don’t turn the date into an interview)
  9. Profile based small-talk (Hopefully light-hearted; discuss something she enjoys)
  10. End or extend date depending on how well it is going

Throwing Out the Script

For all the separation of topic-type I’ve done here and the importance of knowing what you’ll talk about suggested above, most conversation simply doesn’t follow a clear cut model. On most of my dates I followed my script for the first two steps and then the conversation simply took off. It gained a life all its own.

Discussing online dating jump started many conversations to the point that there was no looking back. From there we would jump back and forth between topics talking about things I hadn’t even thought of. As you experience this, the point of the script becomes clear: it’s not for most dates. The script exists only for the dates where the conversation lags. Hopefully, you’ll never need it.

Never try to stick by a script simply because you created one. Mentally tossing the script aside is one sign of a good date.

Taboo Topics

You’ll find lists everywhere about what to not talk about on a first date. Sex, politics and religion are often at the top, although recently I saw an article that said talking about your pets would doom any date (don’t ask me).

I’ve found that lists like this are good general guidelines but that every situation is different. For example, when I met my wife for the first time, a big part of why I contacted her was because of our religious similarities. This seems like safe ground to cover to me at the time (it was).

We also discussed politics on our first date but when I sensed she didn’t like that we disagreed on some ideas I abandoned the conversation quickly. My advice would be to trust yourself more than some list of do’s or don’ts. If your date listed being a member of the Rainbow and Butterfly Tree-hugging Club in their profile but you’re the president of the Vast Right-Wing Conspiracy Fan Club, hopefully you’ll have the sense to exclude political discussion (as long as you can accept views different from yours in your partner).

On the other hand, don’t talk about something you’re not comfortable with just because some other list says you should. Personally, I never brought up sex because I would have been uncomfortable doing so. Healthy conversation is fueled by the comfort of both you and your date so don’t go and slow the conversation down because you think you need to cover certain topics. Use your head and remember that good topics for some dates should be avoided at all costs on others. Lists of suggested do’s and don’ts aren’t bad but it is bad to adopt a universal rule for every date.