First Dates in a Foreign Language – Use these Questions to Avoid Awkward Conversation

Free association is the mother of all great conversationalist skills.  The ability to riff endlessly off nothing at all is sought after by any guy that has ‘run out of stuff to say’ with girls.  

It’s completely possible to work on your chops until you’re at a point where you can turn anything in your environment into a conversation that threads for hours and hours.  It’s probably my favorite thing to do;  pull the girl into a conversation that whips her around like a damn tilt-a-whirl while making just enough pit stops into deep emotional/vulnerability territory. 

Over the years I’ve gotten quite proficient and speaking like this, and my results in dating have easily 10x’d. Especially in the nightclub, the longer you can stay in a good conversation the better your chances are at actually connecting. Certainly not just a words +  volume game but you get my point.

Then I switched to speaking Spanish on dates (in South America) and was completely fucked.

I’ve worked really hard at becoming proficient in Spanish over the last year or two. And for the most part I’ve succeeded in becoming completely conversational.  I can chat up anyone, get things done, navigate a bureaucracy, pick up girls on the street, all in Spanish.

But when you’re sitting face to face (or ideally next to) a girl for a multi-hour (first) date, my Spanish vocabulary can be exhausted within the first 30 minutes (or hers depending). 

Free association in a foreign language is about 100x more difficult. I can think of and articulate a  direct thought or point, but I struggle to continuously flow to the next and the next.

So I use a cheat sheet.

My strategy is to use a list of engaging questions that I’ve written down in a google doc. The questions range from light and cute, to sexual, to emotionally deep.  Based on the vibe and the girls response i can pick which types to continue with and which to skip over.

Each question provokes not only a response, but an awesome thread of a conversation you can use to carry you for a long time (should you want to). 

And the best part? You don’t even have to memorize them all.

I turn the list into a fun thing that I “just thought of”. I say something along the lines of:

“My friend sent me this list of fun first date questions”  


“When i was super young, I had this list of crazy first date questions, let’s see if i still have it…”

In every single case, the girl is intrigued by the list and/or relieved that she doesn’t have to try and help carry the convo in a tough language. Win for everyone.

Then I pull out my google doc, and browse through and find a question that fits the vibe and her personality. From there, they always ask for more and it turns into a fun game you’re playing together.  

Having a little list like that lets you focus on her responses, and actually connecting and finding commonalities among your hopes/dreams/fears.  Instead of just sweating the next sentence that’s going to stumble out of your mouth, you can use them to buy time to think a step ahead.

Here they are (in no particular order).

 My Personal Favorites

1.-What do you judge a guy on when first meeting him? 

2.-Craziest place you’ve had sex.

3.-Ever been caught having sex 

4.-Worst first date story 

5.-First impressions of each other

6.-How do you want your friends to describe you?

7.-What movie characters do you most identify with, good/bad

8.-3 things you want to learn how to do before you die

9.-If you could be an animal for a day, what would you be? Why? What would you do? 

All the rest.  These were taken from somewhere but I can’t remember where to cite them properly.

1.-Given the choice of anyone in the world, whom would you want as a dinner guest?

2.-Would you like to be famous? In what way?

3.-What would constitute a “perfect” day for you?

4.-When did you last sing to yourself? To someone else?

5.-If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

6.-Do you have a secret hunch about how you will die?

7.-If you could change anything about the way you were raised, what would it be?

8.-Take four minutes and tell your partner your life story in as much detail as possible. 

9.-If you could wake up tomorrow having gained any one quality or ability, what would it be?

Set II

1.-If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

2.-Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

3.-What is the greatest accomplishment of your life?

4.-What do you value most in a friendship?

5.-What is your most treasured memory?

6.-What is your most terrible memory?

7.-If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why

8.-Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

9.-How close and warm is your family? Do you feel your childhood was happier than most other people’s?

10.-Make three true “we” statements each. For instance, “We are both in this room feeling … “

11.-Complete this sentence: “I wish I had someone with whom I could share … “

12.-If you were going to become a close friend with your partner, please share what would be important for him or her to know.

13.-Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

14.-Share with your partner an embarrassing moment in your life.

15.-When did you last cry in front of another person? By yourself?

16.-Tell your partner something that you like about them already.

17.-What, if anything, is too serious to be joked about?

18.-If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

19.-Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

20.-Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.


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