Four Must-Ask First Date Questions


What questions should you ask someone on a first date? The four questions below provide a nice springboard, designed to motivate further conversation without making your date feel interviewed or cross-examined. Ask these questions and you can potentially get gobs of good information to mentally feast on later!

1. What kind of relationship are you looking for?

Ideally, any man or woman to whom you’d pose this question would be able to give you a fleshed-out and specific, clear response. Unfortunately, this type of question is so direct that it can actually throw someone off for a second. After all, people are more accustomed to psychological games during dating than direct honesty. When you ask the question, give your date a few prompts to ensure that you get the most honest answer. “Are you looking for something casual, or an exclusive relationship? Some people just want a hookup, while others are gunning for marriage. Where do you fall in the spectrum?” I promise you: The more you learn to ask this question of your dates early in the dating process, the more successful your relationships will be. It really is that simple!

2. How often do you like to talk to or see someone when you start dating them? Are you a slow starter or do you like to dive right in?

Few people employ this question early in dating, and a lot of relationships end because the couple doesn’t draw sufficient boundaries early. What usually happens? Person A meets Person B, and Persons A and B start talking every day and seeing each other – and sleeping together, thankyouverymuch – at least a few days per week. Simply put: No! If you find someone you like and you want it to work, the smartest strategy to protect the future of that relationship is to start the relationship slowly. To make sure things start slowly, try saying this:

“I like you, and I like seeing you and talking to you. But to make sure we don’t jump in too fast or force things, let’s start slowly by seeing each other once or twice per week in the beginning. Is that okay? I like you enough that I don’t want to rush this. Trust me: It’s actually a sign that I like you.”

3. Are you more of a go-out person or more of a homebody?

This one is huge, folks, so we have to spend a little more time on this issue. One of the biggest reasons new relationships fail has to do with socializing – because one person usually likes to socialize more than the other. Whichever you are – homebody, social butterfly, someone in between – know what you are, don’t be afraid to be honest about it, and understand that there must be enough of a similar social style between the two of you for a relationship to work.

Here’s an example of a problem that frequently develops when one member of the couple is more social, and the other is more of a homebody:

Mr. Social loves to watch the game at the bar with his buddies or his girlfriend, and he loves house parties and occasions to meet new people and bump into old friends. Ms. Homebody, however, prefers to chill out at home: cook, garden, or snuggle under blankets to guilty-pleasure TV. After a while: He starts to resent her, gets anxious and restless, and starts acting out. His version of acting out includes losing his temper or going out with his buddies without her, which causes an even greater divide between the couple, frequently leading to the end of the relationship.

Here’s the correct way to handle a relationship in which two people vary in how social they are:

Mr. Social wishes his girlfriend, Ms. Homebody, would go out with him more socially, but he accepts that she isn’t – and is never going to be – very social, and he doesn’t stay home to appease her or force her to go out with him. Similarly, in a healthy relationship, Ms. Homebody would love it if her boyfriend liked to nest at home more, but she knows that’s not who he is, so she finds ways to fulfill herself emotionally at home when he’s out and about.

4. What’s your dream job?

Asking this question is a great way to get a sense of the spirit that lies deep inside the person you’re dating. Sure, he may be a teacher or stock broker, but is that what he does for money, or is that his true passion? Most men and women, sadly, aren’t working in a career that reflects their significant interests and passions – everyone’s too busy paying the bills to have that luxury. Remember, working at a job that isn’t your passion isn’t anything to fault. The point in asking the question is to pull out the little boy or girl inside and get a quick flash of their essence. For example, I recently asked a rather shy friend this question, and she shocked me when said she’d be an actress. I pressed on. “Comedy or drama?” “Drama,” she answered as if she’d been planning this answer her entire life. Well, I never would have guessed it, but asking the question gave me a great window into a sort of hidden part of her personality. Sometimes you can get some really interesting information from your date if you ask this question.

The questions I present here are a few great conversation starters, and will hopefully give you a better sense of who your date is. If you choose to use them, space them out throughout the date as opposed to firing them off like cannon balls. Stay relaxed, let the conversation flow, and enjoy that moment in your life!

book_Dr_Seths_Love_Prescription_lgAbout the Author:

Dr. Seth is a licensed clinical psychologist, author, Psychology Today blogger, and TV guest expert. He practices in Los Angeles and treats a wide range of issues and disorders and specializes in relationships, parenting, and addiction. He has had extensive training in conducting couples therapy and is the author of Dr. Seth’s Love Prescription: Overcome Relationship Repetition Syndrome and Find the Love You Deserve.      


If this article gave you the confidence to find your match, try eharmony today!

Join Now