The Best 1st Date Questions Release by Pittsburgh Dating Service

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Congratulations, you found an awesome guy to go out on a date with, and he’s super handsome too. You have your outfit picked out, you have your hair styled, you’re about to walk out the front door, and then you realize you’re about to go out on the town with someone you know nothing about. So what do you talk about? Well, panic no more.

Today, our Pittsburgh dating experts here at Pittsburgh Singles Dating Service have some of the best topics for you to discuss on your first date. We also have some helpful advice for smooth communication on while you’re out.

If you are a nervous chatterbox like most women, you might spend first dates talking about anything and everything just so you can cover up any awkward silences. Or, maybe you’re the complete opposite and you get your tongue tied and lose your words. Whatever the case, it’s best to be prepared. Just bringing a few questions to your first date will get you prepared so that you can come out successful. After all, you are only responsible for 50% of the conversation that happens on a first date.

To get you started, our Pittsburgh dating experts here at Pittsburgh Singles Dating Service have some great questions to use on your first date. These questions will help you get to know him and find out if you’re compatible for one another.

1. What Do You Do During Day?

This is an open-ended and very casual question to start off your first date. Men especially love talking about their careers, and for most men, their careers are what define them so they usually can’t stop talking about them. We like this question because it asks him if he has a job without assuming, and it allows him to tell you certain details that he wants to share with you.

2. What Does Your Perfect Sunday Look Like?

This question reveals a lot about a person, more so than you think. If your Sunday usually involves going out for brunch with the ladies, followed by a walk in the park, then curling up with a book at home with your furry feline friend, while his consists of watching football and drinking beer with a rowdy group of guys all day, then the two of you might not be compatible for each other. You see? This question reveals a lot about a person.

3. Are You From Around Here?

It is a little too much to give this man the third degree when it comes to his parents, siblings, and social economic background; however, this is a much better question to ask him as it’s polite and less intrusive. You’ll be surprised how much you can find out about a person just by getting them talking about their background and family.

4. What Do You Want to Do When You Get Older?

This is a great question to ask any man on a date. This question is great as it’s a good way to inquire about a number of things, including their ultimate goals and where they see themselves a few years from now. When you were in your twenties, this question came from a playful place and it still does the same, even as a more mature person. This question gives you good perspective into their future.

5. Who Was Your Role Model Growing Up?

This is a great question to spark conversation with him. It also gives you an inside look at your date’s childhood. A person’s role model says a lot about them, who they are, and what their values are, so don’t be shy; find out who he looked up to as a child.

6. Do You Date Often?

This is a great way to find out if he is a serial dater or is out on the search for a long and committed relationship. Yes, you’ll come across many types of single when looking for the one, mature singles who are divorced, some who are serial daters, and some who are just getting back in the field looking for something serious and committed. It’s good to know what dating expectations the man sitting across from you has before you get too invested.

7. What Are Your Pet-Peeves?

For example, does it drive you nuts when someone doesn’t know the difference between there, their, and they’re?
Finding out someone’s pet peeves can give you a heads up if the two of you are going to butt heads or go together like peanut butter and jelly.

How to Maintain a Conversation on a 1st Date…

1. Listen as Much as You Do Talking

Some people consider themselves to be good communicators because they can talk endlessly. However, our Pittsburgh dating experts know being able to speak is just one part of the equation. You must also be able to listen. The best communication happens when two people talk evenly. Think of your first date conversation as a tennis match in which you and your date back and forth. Each person gets their turn, no one is hogging the ball.

2. Peel It Layer by Layer

Getting to know someone is like peeling an onion. You do it slowly but surely, layer by layer. Some people get too overly eager in the conversation and get into deep subjects—too much, too fast. They ask too many personal and sensitive questions that makes their date get defensive. Now, should the relationship get serious, there will be plenty of time to talk about those topics, but for the first date we want you keep these subjects off the table.

3. Show Genuine Interest

Maybe your first date questions will lead you to find out that the person in front of you is your true soul mate, or maybe not. Either way, you are out on a date with someone new and it’s exciting to be able to get to know someone else. Just remember that great communication starts with being genuine about what the other person has to say.

The key to having a successful first date is to have a positive experience with relaxed conversation topics, our Pittsburgh dating experts know it always helps to be prepared with what types of questions to ask as well as which ones to leave off the table during your first date. So now that you know the types of questions you need to ask, your upcoming first dates should go as smooth as butter. Remember to let your date do some talking; after all, it’s all about finding the perfect balance.

For more dating and relationship tips from our matchmakers, be sure to connect with us on Facebook and Twitter!


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