Full disclosure: I do not think I am qualified to write about being insanely interesting on a first date, but “How to be moderately interesting on a first date” doesn’t have the same appeal. Also, I have gone on some first dates with pretty interesting people, so these tips are pulled from those experiences just as much as from my own moderate interestingness. Good news: If you are an insanely interesting person, but get a little nervous when dating, these ideas will totally work for you!

  1. Ask lots of questions. This may seem like it’s about the other person being interesting, but it’s actually about you as well. Here’s the trick: ask interesting questions. It’s not about trying to be too cute (“What’s your favorite dessert?”), too clever (“In Back to the Future, how come George and Lorraine McFly don’t recognize their 17-year-old son as the guy who got them together in high school?”), or too personal (“When was the last time you felt truly vulnerable?”). It’s about stumping the person with mental math! Just kidding. It’s not about any of those things. Asking interesting questions is just a way to show you’re a curious person with a thoughtful mind. Try asking about books they’re reading, what plans they’re most looking forward to, or where in the world they most want to visit.
  2. Do something interesting. I’m actually a big fan of drinks or dinner as a first date activity. Though it’s not particularly original, I just like face-to-face conversation. But doing a more unusual activity where talking is allowed, like going to an art gallery, can make it easier to come up with conversation topics. Here are some other ideas.
  3. Have something to say about your day. First dates often venture into biographical territory (Where did you grow up? How many brothers and sisters do you have?) It’s nice to be able to supplement this with an anecdote from your current life. You’ll convey a lot more about yourself this way, and it will keep the conversation from feeling stilted and “first date-y.”
  4. Have a problem to solve. Of course, you don’t want to go into complaining mode, but sharing a small challenge you’re having at work or with a side project, and discussing possible ways to approach it not only makes for an interesting discussion, it also gives some insight into the way you look at life.
  5. Don’t treat it like a job interview or audition. You don’t need to rattle off a list of your accomplishments, or put on a show, and you certainly don’t need to offer up a five-year plan. Rather than developing a “pitch,” just focus on sharing stories and ideas.
  6. Speaking of ideas…share ‘em. You must have ideas about something, right? Maybe you have strong opinions about the state of education or the state of television. Perhaps you have a list of awesome t-shirt ideas. Whatever you’re passionate about, let it all out. But try to keep it light, k? The point is to be interesting, not scary or obsessive.
  7. Make sure you figure out if you like them. A classic rookie mistake is to focus entirely on impressing the other person. It’s just as important (nay, it’s more important) for you to figure out if you find them interesting (in a friendly, non-judgy way). It might not seem like it, but this will actually make you seem more interesting because you’ll come across as confident rather than over-eager.
  8. Tell a joke. Here’s a good one: Why did the hipster burn his mouth? (wait for it) Because he ate his food before it was cool.

Anything to add?

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