6 Conversation Ideas for Your First Date

Hey it’s Gregg and I’m so excited to bring you a guest blog post from a friend of mine, Pauline Plott. Pauline is a London-based blogger on DatingSpot. You can read her bio at the end of this post! Enjoy!

There you are, sitting down for dinner with a person you hardly know. You exchange pleasantries, talk about the pasta, and then it hits you…

SILENCE.

You’re thinking, “This is not good.” 

Suddenly you’re so tongue tied that you have nothing to do but look down at your food. “Make it end!”, you beg internally.

We’ve all experienced it before, but part of being prepared for a date is coming with a list of conversation ideas that ensures you’re never caught bereft of speech.

Now, let’s explore some of my favorite conversation ideas for a first date. They are guaranteed to inspire, compel, and even build rapport. But first, let’s go over some discussion basics…

Listen More Than You Speak

The point of a first date is to get to know the person you’re with. It’s pretty hard to do that if you don’t give them the opportunity to do so. Listening more than you speak is a good rule to abide by in general, but is especially important on a first date.

If both you and your new friend follow this rule, there will be a fairly even exchange. A good indicator of a relationship “clicking” is the ability to volley a conversation back and forth. Kind of like a ping pong match.

Be Genuinely Interested

No matter how your first date is going, it’s important to give it your all. Part of this can be achieved by showing genuine interest. Even if your date is not the most interesting person in the world, you should still take advantage of this unique opportunity to learn about this person’s unique perspective.

You may find that your concerted effort to act interested actually makes you interested.

Avoid Taboo Subjects

There are certain topics you should always avoid on a first date. One would think that many of these are obvious, but I have been on innumerable dates where these topics have come up. More often than not, when these issues are brought up it was ‘one and done’ for me.

  1. Past Relationships
  2. Money and How You Spend It
  3. Intimate or Sexual Details
  4. Marriage Plans
  5. Politics

First dates are meant to be lighthearted and fun. Mixing in this kind of discussion makes it… Not that. Of course, that leaves plenty of topics that you CAN broach.

Here are just a few…

Conversation Ideas for Your First Date

Now that I’ve discussed the basics, we can talk about some great conversation ideas! Feel free to expand on these and even come up with some that relate to things you discussed during the online dating process.

1. Who has been the biggest influence on your life?

This question is pretty typical and seemingly innocuous, but really says a lot about who a person is and what they want to be in life. If your date talks about a family member, it means they probably come from a healthy and loving home. If they choose to talk about a famous figure, it means that they have a passion for things outside of their own world.

2. Where is your favorite location on earth?

This is a good question for learning about where someone has been and can lead to a much further and deeper discussion about travel. You can also use this response for the planning on dates later on. For example, if your date says their favorite location is Niagara Falls, you can take them on a picnic to a local waterfall.

3. What is your favorite movie ever?

Asking about movies and pop culture in general is a great way to connect with someone. That’s because it is so pervasive that everyone has something to say about movies, TV shows, and celebrities. Once again, the answer to this question can lead you down a conversational path that is rich, interesting, and capable of creating some nice side discussions.

4. What is your biggest goal?

Similar to question one, the answer to this question can tell you a lot about a person. Goals are an indication of drive and people who can immediately identify their biggest goals are often those who don’t need to go on dates to begin considering the matter.

Keep in mind that all of these questions will be volleyed back to you, so make sure you have an answer yourself!

5. What do you hate most about dating?

Nothing brings people together better than a mutual dislike of something. Dating isn’t always fun and everyone has something to say about the matter. Talking about your frustrations together is a surprisingly good icebreaker.

6. What should I know about you that I wouldn’t think of asking?

This final question is my favorite. The things that someone chooses to voluntarily reveal about themselves that may be quirky can say a lot about them. Like all of the other questions on this list, it can also lead to even more interesting and unexpected questions that result, ideally, in both you and your date having an amazing night.

As you may have noticed, one commonality these all share is that they are not ‘yes or no’ questions and require a little bit of thought. Each one can tell you a lot about a person, their expectations, and their dreams.

You may find that you really connect with many of the answers and, perhaps, that you do not.

I always recommend a second date if you think that it’s worth continuing to suss things out.

About the Author

Pauline Plott is a London-based blogger who became a dating guru after learning the psychology behind modern romance and signing up for every dating website in pursuit of relationship bliss. She shares her reviews and opinions on DatingSpot.co.uk.

Gregg Michaelsen

Gregg Michaelsen

Gregg feels that coaching has chosen him. He grew up just as many others – in a dysfunctional, but loving family. After going through twelve years of his own failed relationships, he decided to try and decode dating for men and women. That elusive older couple sitting in the park holding hands gave him hope!

Gregg began his journey into understanding the mistakes we make in dating and how to fix them by interviewing thousands of people – happy couples, unhappy couples, singles looking for ‘the one’ and everyone in between. He reviewed his own dating experiences and combined all of this information into his series of dating advice books for men and women.

Gregg Michaelsen

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