After so many dates, I came across a few conversation starters that are really fun and help you get comfortable with your date fast. The key to using these successfully is not to take them very seriously; just present them to the girl as something interesting and funny to try together. Here's the list:

Dating facts from OkCupid's dataset

Do you prefer people in your life to be simple or complex?

If you answered "simple," you're more likely to be politically conservative. If you said "complex," you're more likely to be politically liberal.

This is just one of the really interesting insights that Christian Rudder describes in his excellent book Dataclysm. Rudder was a founder of OkCupid, and he mined their vast dataset for interesting tidbits like this. The book is fascinating, and as it happens, these facts are great to discuss on dates. They give you insight into the woman you're on the date with, they open up the conversation to romance/sex, and they make you seem intelligent and interesting for knowing them.

Some other great facts:

  • People who like the taste of beer are 60% more likely to consider sleeping with someone on the first date.

  • People who are bothered by spelling and grammar mistakes are less likely to be religious.

  • A couple's shared preference for horror movies correlates strongly with relationship success. So if one partner likes horror movies and the other doesn't, their relationship is a lot less likely to last than if they both liked horror movies or both disliked them.

I've found that it's easy to work these into a conversation, and you can do it even if you haven't read the book. Just act really excited about them-- tell the girl, "I just heard of this really interesting trick. I bet I can predict if you're religious or not!"

In my experience, once you tell the girl about the facts and where they came from, she'll want to hear more, and you can tell her the others. I suggest finishing with the "taste of beer" question, since it's the most fun!

What's your ideal body of water?

This is a fun little game that I learned way back in 5th grade, and I've been using it for my amusement ever since. You tell the girl you have a little psychological test for her, and then ask her the following questions:

  • What's your favorite animal? Describe it in as much detail as you can.

  • What's your favorite color? Describe it in as much detail as you can.

  • What's your ideal body of water? Describe it in as much detail as you can.

Then, you share with her the corresponding "meanings" of the answers:

  • The animal describes how you'd like other people to view you.
  • The color describes how you view yourself.
  • The body of water describes how you think about your sex life.

This one is much less fact-based than the OkCupid questions, but it's always good for a laugh, especially when someone describes the water as wild and dangerous, or vast and dark. More importantly, it opens the conversation to deeper, more meaningful topics.

The Infamous 6-12-18-24 Challenge

This is a pretty unique thought experiment and a real-life challenge that I learned in college. It's a bit tougher to bring up casually, and you should definitely establish a rapport with someone before asking this, but everyone I've talked about it with has had a lot of fun with it.

The challenge is this:

There are four groups of activities: Eating donuts, running miles, drinking beers, and having orgasms.

To complete the challenge, you must do one of these things 6x, one of them 12x, one of them 18x, and one of them 24x. You have to do all of this in under 24 hours. For example, you could have 6 orgasms, run 12 miles, drink 18 beers and eat 24 donuts.

People enjoy contemplating the various limitations and possibilities of this challenge, and it's interesting to see peoples' attitudes towards each category. I once told a girl I didn't think there was any way I could ever have 12 orgasms in 24 hours, and she said, "thanks for the vote of confidence!"

That was a fun few months.

36 Questions to make you fall in love This was an old psychology study which became popular recently when the New York Times ran an article about it. Basically, a researcher came up with 36 questions designed to make two strangers "fall in love" after asking them of one another. The activity peaks at the end, when you're supposed to stare into the eyes of the other person for 3 minutes straight-- it's surprisingly intense!

I've actually tried this twice, and it's been interesting both times. I didn't fall in love with either girl, but the questions definitely accelerated our relationship and got us talking about real things. I won't list all the questions, but you can find them on the NYT website here

Doing this entire activity or just discussing it can lead to interesting conversation about love, attraction and what it means to you and your date.

A walk to a lover's house

I hesitate to include this one because it seems like something you'd read in a Cosmo Teen magazine, but it's still kind of fun and girls I've done it with have really enjoyed it. Like the Body of Water quiz, it's a list of questions with corresponding interpretations. Here are the questions:

  • You have a lover who means everything to you. He lives apart from you, but within walking distance. One day you decide to visit him. You have two paths you can take to get to his home. One is a short but boring path that will get you there quickly. The other is a long but scenic path with many beautiful sites that will take longer. Which do you take?
  • Along the path you come across rose bushes. The roses come in two colors — red and white. You decide you want to pick some roses for your lover. You are allowed to pick twenty roses of any combination of red or white. How many red and how many white roses do you pick?
  • You go up to his bedroom and he is not there. You want to leave the roses in his room. Do you leave them on his windowsill or on his bed?
  • Your lover returns and you two spend the night together. You both fall asleep and in the morning you wake up first. Is he awake or still sleeping?
  • It’s the end of the day and time for you to say goodbye and go home. Again, you have can take a long but scenic path or a short but boring path. Which path do you take?

The corresponding interpretations are:

  • If you took the long path, it means you take a long time to fall in love. The short path means you fall in love quickly.
  • The white rose bush represents selfishness in a relationship, while the red rose bush represents selflessness. The makeup of the bouquet indicates how selfish/selfless you are.
  • If you left the flowers on the bed, you prefer an intense relationship where you see your lover a lot. If you put them on the windowsill, you like your space.
  • If your lover is still asleep, you don't feel the need to change your partner in a relationship. If they're awake, you're more controlling.
  • If you take the long path home, you fall out of love slowly. If you take the short path, you get over breakups quickly.

Use them wisely! These are definitely not magic and they're no substitute for being a generally good conversationalist (a subject which many people smarter than I am have written extensively about).

But I've found that they can transform an otherwise mundane first date into a really fun conversation, and can do wonders to make you and your date feel comfortable with each other.

I like writing about this kind of thing. You can read more here.

Good luck, and let me know how it goes!