15 Questions that Will Turn an Awkward First Date into an Amazing One

When nerves get the best of us, we can easily turn a first date, where you are just trying to get to know one another, into something that resembles a game of 20 questions or worse, an interrogation. If you really want to go out on a second date with the cutie on the other side of the table, you can try asking these 15 questions.

1. This coffee reminds me of the best cup I had while traveling to [insert city]. Isn’t it interesting how things can remind you of something from your past?

With this type of question, you are incorporating a memory of your past with a present day situation. It’ll give him a chance to share something about himself and the conversation could become quite interesting pretty quickly — depending on the answer.

2. It’s a shame that theaters don’t do double-features anymore… What’s the most number of movies you’ve seen in one day?

This question gives him information about yourself and then allows him to elaborate and share some information about himself without feeling like he is being grilled.

3. Do you remember that scene in [insert movie] where they are swimming under the stars? It reminds me of skinny dipping as a teen in the neighbor’s pool. I miss doing those sorts of things… Have you ever done anything like that?

This question shows that you’re adventurous and a bit risqué, but the flirtatious intention will clearly be noted. If he responds by saying he has done something like that in the past, then be prepared for more flirty conversations to ensue.

4. What brought you to [insert city]?

This is a good question to ask if they are a transplant, whether from out of state or simply from another town.

5. Where do you normally like to hang out in your spare time?

This lets you get an idea of their hobbies and what they enjoy doing. If you share similar places of interest, it is the perfect opportunity to plan a second date.

6. What was it like growing up with [x-amount of siblings]? Or What was it like being an only child?

Depending on the familial structure of his family, this question will clue you in to how he became the person he is today.

7. If you could only eat one type of food for the rest of your life, what would it be?

This question will give you a glimpse into the things your date likes the most. For example, if they say they could live off of steak and cheeseburgers for the rest of their lives, then they may not be the most compatible if you’re a vegan. Of course, this shouldn’t be the end all, be all of getting to know them – it is a hypothetical question of course.

8. Where are some of the places that you’ve always wanted to visit?

With this question, you will learn if they like to travel or if they’d rather stay home. We like asking this question because it’ll give you an idea of whether or not they are content in their own little bubble, or if they have insatiable wanderlust.

9. What is your personality type?

This is the question you’ll want to ask if you have a hard time figuring out that person. Not only that, but you can get a better idea if you’re compatible. For instance, it may be difficult for two alphas to get along, or maybe you’re an introvert and you don’t want to get involved with an extrovert.

10. What are some of your biggest pet peeves?

We all have them, and we all know someone who pushes your buttons on purpose. By asking your date what are their biggest pet peeves, you’ll know what things to avoid (if you want a second date) or what things to do (if you don’t want a second date!).

11. If money were no object, what would your dream vacation be?

This is a wonderful question because you can easily have an engaging conversation. Also, if you’ve been to your date’s dream vacation destination, then you can fill them in on how wonderful the place was, and where they need to go for the best experience.

12. What was your favorite cartoon you used to watch as a kid?

Reminiscing over your favorite cartoons as a kid is a great way to spark conversation – especially if you are around the same age. You may find that you share favorite cartoons. Also, by talking about your favorite cartoons, it could easily lead to more conversations about what your childhood was like, the things you miss most about being a kid, and even muse over how differently children behave today than when you were growing up. See? Lots of potential with this one!

13. Did you have a pet when you were growing up?

Again, this is another good conversation starter because most of us had a beloved pet as a child, or wanted a pet but they weren’t allowed to have one. With this question, you’ll have the opportunity to get a better understanding of their home life as a child, but it can also lead into a conversation about current pets and the like.

14. What is the happiest moment in your life?

With this question, you should prepare yourself to answer in kind. However, who doesn’t want to share the happiest memories of their lives? You can also get an idea of what is most important to them.

15. What are your plans for the following weekend?

This question shows your interest and your intention to spend more time together. Be bold and ask for a second date!

After all is said and done, the conversation you have and the questions you ask will set the tone for your date. If you are having a hard time meeting people on your own, you should sign up for a membership on Flirt.com! The members of our site are friendly, engaging, and are always down to have a good time! Of course, don’t take our word for it. Try it yourself! What have you got to lose?