Questions to Ask on a First Date

Things you need to know when you first meet him

There's no better time to ask questions than on a first date. If you ask too many questions on, say, a third date, after being quiet on the first two dates, then he'll think you're grilling him for no reason. So go ahead and throw out the big stuff on the first date and find out if he's the one for you before you pursue a relationship.

After all, wouldn't you rather know on the first date that he hate kids or wants to wait until he's 40 to get married? No matter how much you like him, it's always easier to end it early than six months down the road.

With that in mind, we turned to our dating experts to ask them the top 15 questions to ask on a first date.

Questions to Ask on a First Date

Do you like animals?

This is a natural question and will give you insight into his personality. It’s also a good starter question to keep the date from feeling like an interrogation.

What are some of your favorite restaurants?

Everyone likes food, so this is something people can relate to and not feel high pressure.

What sports teams do you follow or are you interested in?

Again, this question connects people to family traditions, college, and is also low-pressure.

What are some of the things you like to do on the weekends?

It's also good to let your date know what you like to do as well to make the conversation balanced.

Have you ever been out of the country?

This is a more relaxed question that a lot of people can relate to and easily find conversation to talk about once you know where he’s traveled and if you have any places in common.

Where have you traveled recently?

This is a natural follow-up to the previous question. Some people like to go to Europe to sightsee others like to head to Miami to party. You can learn a lot about people when they describe their travel personas. You can find out first and foremost if you have a connection. It's a great conversation starter if you've both visited the same place or have a favorite dream travel spot. It helps the conversation flow much more fluidly than the typical ‘where are you from?’

Do you like what you do?

Asking about his job allows you to assess his financial stability, without asking for a pay stub. Furthermore, for many men ego and job go hand-in-hand. If he’s unhappy with what he’s doing, the stress is going to permeate other aspects of his life.

Questions to Ask on a First Date

Did you go away for college?

This will allow you to know if he actually went to college, and possibly find out if he has a degree, without it feeling as if you’re grilling him. Plus, you’ll find out if he attended a quality school, or if he went to a state college, if that matters to you.

What do you do for fun?

You’ll be able to find out if his interests and pursuits match yours as well as assess his proclivity for good health and longevity. If he says he is inactive, he might not be the right guy for you.

Are you close to your family?

If he’s close to his family, then it shows that he understands the importance of maintaining relationships long-term.

What’s your mom like?

The kind of relationship he engages in with his mother is a keen insight into how he’ll treat all the women in his life.

What did you and your family do for vacations when you were young?

This will give you an idea of what he was exposed to, how he was enculturated or emotionally developed. If they traveled together, or took separate vacations, or went away at Christmas, will tell you volumes about his personal preferences.

What was the longest romantic relationship you’ve ever had and why did it end?

This is serious stuff, but essential. Questions in this area will help you determine how he views relationships, if he takes responsibility for his actions and how he perceives or interacts with a woman he is involved with.

Are you interested in a long-term relationship or just looking to date casually?

This might seem like an obvious question for a guy to lie about, and say he wants something long-term even if he doesn’t, but it’s actually a question that most men answer honestly. Listen to what he says and believe it. If he says he’s looking for fun, then that is what he is looking for.

Do you like kids and do you ever see yourself becoming a parent?

Again, this is a serious question, but the first date is the best time to ask. If you ask this on the third date, then it seems like you’re plotting your future engagement. But on the first date it’s a natural question to throw out there.

Sources: Stef Safran, owner of Chicago-based dating service Stef and the City; Kerri Zane, spokesperson for online dating site; Tina B. Tessina, Ph.D.; Jill Jacinto; and Dawn C. Reid

Tagged in: dating, relationships, first date,

Lifestyle / Relationships

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