ArtsAutosBooksBusinessEducationEntertainmentFamilyFashionFoodGamesGenderHealthHolidaysHomeHubPagesPersonal FinancePetsPoliticsReligionSportsTechnologyTravel

Good Questions to Ask a Woman on a First Date

Updated on May 2, 2023
Sychophantastic profile image

I'm an eclectic gal with many diverse interests. They include relationships, film, trivia, and an assortment of other things.

Think of dating like a job interview

Guys who are desperate think of a first date as a chance for them to interview for the position of being the boyfriend of the woman they are meeting. A guy with confidence thinks of a first date as a chance for the woman to interview for the chance to be his girlfriend. The first step in approaching the dating game with the right attitude is thinking of it as a job interview for the woman you are meeting. Even if she doesn't know it, the woman is interviewing and you're going to evaluate her and see if she meets your standards. Don't settle for a woman who doesn't pass the test.

Having made the analogy between a first date and a job interview, the intention of these questions is for them to come up in casual conversation, not for the man to whip out a list and start asking them like he's in an interrogation. Be subtle. Gentle. You don't have to ask every question and you don't have to ask them in any particular order or using my exact words. You're trying to create a good conversation, but also get information. Doing so is a skill, so practice.

The ultimate thing to understand though is that if you give the woman the idea that you're the one in control, that she's interviewing for you and not the other way around, it will help overall attraction. You want to give the impression that you're the one doing the choosing.


Use these questions or some variation to start some good conversations

Where Do You See Yourself in 3, 5 or 10 Years?

What you're trying to find out here is whether a woman sees herself married, with children, or an entrepreneur making tons of money. This tells you what she wants out of you because a woman who says "oh, I'll be taking care of my five children at home in my mansion" is a lot different than one who says "I'll own my own business and be making a million dollars."

Describe the Worst Date You've Ever Been on

What a woman considers to be a bad date will tell you a lot about her. It will tell you a lot about what she likes in a man and doesn't like and it will give you great insight into her tastes and what kinds of behaviors you might want to avoid.

Describe the Best Date You've Ever Been On

See #2. However, don't take what she says literally. You're trying to pick out themes, behaviors; etc. You're not trying to repeat the exact details of the date.

Describe Your Dream House

Depending on what kind of guy you are, you want to know what a woman's relationship to money is. Does she even care what kind of house she lives in or does she say something smart like "it doesn't matter what kind of house I'm in as long as I'm with the right person."

Would You Rather Bar Hop or Sit at Home with a Good Book?

This question tells you whether a woman is an introvert or an extrovert and whether she values intelligence more than socializing. If you're a party animal, you don't want to go out with the former. If you're a bookworm, you probably don't want the latter.

What Would Your Ex-Boyfriends Say About You?

This is a fun question for a whole bunch of reasons. First, it's just a good question. You're likely to get a lot of good detail from a woman who you'll want to see again because a woman with confidence and intelligence is going to tell you stuff. She's not going to be ashamed of why she broke up with past boyfriends. And if she's the kind of woman you'll want to hang out with, she's not going to have any big skeletons in her closet. However, a woman who's going to throw up red flags is also going to give you some interesting detail. She's probably going to tell some ridiculous stories. She's probably going to have a whole sequence of stories about ex-boyfriends who were unbelievably freakish. Well, freaks attract freaks. One way or another, you'll learn some interesting stuff. And a woman who won't tell you anything probably has something to hide.

Describe Your Favorite Meal

I find that eating is a critical component of both attraction and compatibility. You want what you believe to be good food to match what your woman thinks is good food. If you like McDonald's and she likes sushi, you might want to rethink your interest.

What Do You Like Best About Your Parents?

You're looking for a bunch of details in this question. First, you want to find out about the relationship between a woman and her parents. Usually a strained or non-existent relationship signals a problem. A preference for one parent or another will tell you lots about your woman. If she's a daddy's girl, she's likely to be looking for similar qualities in her man that she likes in her father. Not a daddy's girl. Similar reasoning applies. Remember, a woman's father is the first and most significant male role model in a girl's life. Pay attention to what she thinks of her father.

Define Success

Is success money or happiness? That's what you are trying to find out from the woman. If the woman talks about material things, then you know what kind of career you're going to have to have to make her happy. If the woman talks about helping others and having a great family, then you know where she stands too. Ultimately, the answer will tell you loads.

Do You Prefer Cats or Dogs?

People have strange relationships with their pets - women especially. You might want to find out if the woman you might be dating is crazy, like if she thinks her pet is a person or deserves to vote or she dresses it in clothing.

© 2012 Sychophantastic


This website uses cookies

As a user in the EEA, your approval is needed on a few things. To provide a better website experience, uses cookies (and other similar technologies) and may collect, process, and share personal data. Please choose which areas of our service you consent to our doing so.

For more information on managing or withdrawing consents and how we handle data, visit our Privacy Policy at:

Show Details
HubPages Device IDThis is used to identify particular browsers or devices when the access the service, and is used for security reasons.
LoginThis is necessary to sign in to the HubPages Service.
Google RecaptchaThis is used to prevent bots and spam. (Privacy Policy)
AkismetThis is used to detect comment spam. (Privacy Policy)
HubPages Google AnalyticsThis is used to provide data on traffic to our website, all personally identifyable data is anonymized. (Privacy Policy)
HubPages Traffic PixelThis is used to collect data on traffic to articles and other pages on our site. Unless you are signed in to a HubPages account, all personally identifiable information is anonymized.
Amazon Web ServicesThis is a cloud services platform that we used to host our service. (Privacy Policy)
CloudflareThis is a cloud CDN service that we use to efficiently deliver files required for our service to operate such as javascript, cascading style sheets, images, and videos. (Privacy Policy)
Google Hosted LibrariesJavascript software libraries such as jQuery are loaded at endpoints on the or domains, for performance and efficiency reasons. (Privacy Policy)
Google Custom SearchThis is feature allows you to search the site. (Privacy Policy)
Google MapsSome articles have Google Maps embedded in them. (Privacy Policy)
Google ChartsThis is used to display charts and graphs on articles and the author center. (Privacy Policy)
Google AdSense Host APIThis service allows you to sign up for or associate a Google AdSense account with HubPages, so that you can earn money from ads on your articles. No data is shared unless you engage with this feature. (Privacy Policy)
Google YouTubeSome articles have YouTube videos embedded in them. (Privacy Policy)
VimeoSome articles have Vimeo videos embedded in them. (Privacy Policy)
PaypalThis is used for a registered author who enrolls in the HubPages Earnings program and requests to be paid via PayPal. No data is shared with Paypal unless you engage with this feature. (Privacy Policy)
Facebook LoginYou can use this to streamline signing up for, or signing in to your Hubpages account. No data is shared with Facebook unless you engage with this feature. (Privacy Policy)
MavenThis supports the Maven widget and search functionality. (Privacy Policy)
Google AdSenseThis is an ad network. (Privacy Policy)
Google DoubleClickGoogle provides ad serving technology and runs an ad network. (Privacy Policy)
Index ExchangeThis is an ad network. (Privacy Policy)
SovrnThis is an ad network. (Privacy Policy)
Facebook AdsThis is an ad network. (Privacy Policy)
Amazon Unified Ad MarketplaceThis is an ad network. (Privacy Policy)
AppNexusThis is an ad network. (Privacy Policy)
OpenxThis is an ad network. (Privacy Policy)
Rubicon ProjectThis is an ad network. (Privacy Policy)
TripleLiftThis is an ad network. (Privacy Policy)
Say MediaWe partner with Say Media to deliver ad campaigns on our sites. (Privacy Policy)
Remarketing PixelsWe may use remarketing pixels from advertising networks such as Google AdWords, Bing Ads, and Facebook in order to advertise the HubPages Service to people that have visited our sites.
Conversion Tracking PixelsWe may use conversion tracking pixels from advertising networks such as Google AdWords, Bing Ads, and Facebook in order to identify when an advertisement has successfully resulted in the desired action, such as signing up for the HubPages Service or publishing an article on the HubPages Service.
Author Google AnalyticsThis is used to provide traffic data and reports to the authors of articles on the HubPages Service. (Privacy Policy)
ComscoreComScore is a media measurement and analytics company providing marketing data and analytics to enterprises, media and advertising agencies, and publishers. Non-consent will result in ComScore only processing obfuscated personal data. (Privacy Policy)
Amazon Tracking PixelSome articles display amazon products as part of the Amazon Affiliate program, this pixel provides traffic statistics for those products (Privacy Policy)
ClickscoThis is a data management platform studying reader behavior (Privacy Policy)