Best Questions to Ask on a First Date


1. Don’t ask Questions Make Statements - Statements are how we have conversations with friends. We pepper questions in there every now and then but mostly we say stuff and trust that they will respond.

2. If you must ask questions ask leading questions - This is important for guys, but ask pointed questions every now and then. It will make her ask herself “Why did he have that assumption?”

Examples: “You like cats right?” “You’re from the East Coast, huh?”
“You look like you like to travel?”

3. Tell Stories - Get really good at telling stories people. Make sure you pick out good details, change your tone, the and smile a lot. I always recommend trying to make the mundane interesting on dates.

4. But if you absolutely must ask question here are some questions to get them off their script

“What did you eat for breakfast?”
“Why do people talk to each other about the weather?”
“If you had only bullet and you were in a room with Stalin and Hitler, who would you kill? ”
“Do you like peanut butter?”
“I’m thinking about getting a fish - what color should I get?”


These questions are off the wall and more than likely most of you will feel weird saying them. I don’t want you to copy my question verbatim but I want you to look at the spirit of the questions, they are fun, superficial, weird but not try hard.

This will make the date more playful which is what dates should be. They shouldn’t be this long discussion about your hopes and dreams from the beginning. I’ve had a bunch of dates like that and frankly they’re boring and insincere.

A lot of times, if I am being honest I don’t really care about her answer, I’m just trying to keep the conversation going.

With these new types of questions and making statements I have so much more fun with the girl when I’m out. Sure I’d like the date to end at her place or mine, but if it doesn’t I don’t care because I had fun.

If she hates my sense of humor/statements/questions/stories well I shouldn’t have been with her anyway. I don’t want to be around someone I have to filter myself to relate too. I already do that enough at school during the day - I’d to leave school and do that with the person I’m trying to cultivate a loving relationship with.

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