Master the Art of Dating with Philadelphia Upscale Matchmakers

Dating has definitely changed in the last few years.  Nowadays, men are meeting single women through much different platforms.  Although online dating sites and dating apps make connecting with local singles quick and easy, people aren’t going out on dates as much as they once did.  Less dating experience means more troubles planning. 

Part of what makes a killer date is proper planning.  If you want to be successful with women in Philadelphia, you must know how to properly plan a great date.  If you want to land a girlfriend, you must plan a date that helps you spark a connection and make a lasting impression.

In our near 30 years of operations in the Philadelphia dating industry, we have taught many men the art of dating.  The first date is crucial, and it will set the tone for your relationship. So get ready to discover the ultimate way to plan a great date in Philly.

It should allow for plenty of relaxed conversation.

In order to ensure that you have a great date, you must choose a place that allows for easy conversation, which will require a little time and efforts on your part.  After all, we all know that first date conversation can be a little awkward, especially because you’re just meeting this woman for the first time.  You should pick a date that encourages lighthearted conversation.  The atmosphere should give you many things to talk about to kill those awkward silences that usually pop up.  Having something to talk about will take the pressure off of both of you and allow more fun to be had.

Plan a date with mutual interests in mind.

Whether you met her at a coffee shop, local bar, or through our matchmaking services, you should have an idea of who she is and what she likes.  Common interests will be beneficial for your date planning.  Dates that allow you and her to engage in a mutual interest will give you many interesting things to talk about.

If you choose a date revolving around both of your mutual interests, it will let her know that you were paying attention to something she said when you first met her.  It is important to show a woman you’re interested right from the get-go, and you can do this by choosing a great date activity.  Picking a date based on mutual interests will also show her that you’re compatible. 

Plan a date with a timeframe in mind.

Dates that have a timeframe are much better than free-for-alls.  If you go out for coffee, make sure there is a time limit.  Why would you want to do this?  Because you don’t know how things are going to go just yet.  When the date is over, you can always extend your date if things went well.  If you had a good time and would like to continue, you can ask her if she wants to go for a walk in the park, to check out a nearby art gallery, or to grab a drink at a local lounge. 

On the other hand, if the date did not go as planned, you’ll have an easy way out.  It is easy to extend a date that has a time limit.  However, if you arrange a long date and things aren’t going well, you’re stuck.  Our Philadelphia upscale matchmakers know timing plays a huge part in planning a great first date.

Date ideas that work…

We have given you some guidelines to plan a successful date.  But now you’re probably looking for some examples of where you can take her in Philly.  Don’t worry, our Philadelphia upscale matchmakers have you covered.  Here are a few examples of dates you can plan to have a great time together.

  • Games Dates: Bowling, mini-golfing, go-cart racing, and driving golf balls are just a few ideas of game dates. These are great ideas that allow for plenty of conversation and fun to be had.  They also have a time limit, which allows you to continue the date or end it right then and there.


  • Walking Dates: Simple but effective. If you’re both into the outdoors, why not take her out on a refreshing walk at the local park?  Walking dates are a great way to get to know each other while escaping the pressure of sitting together at a restaurant.  You can either walk your dogs, visit a historic site, a park, the river, or you can take it up a notch and go for a nice hike.


  • Activity Dates: If you both enjoy being active, use it to your advantage. For example, if you already know she is into working out, then you can invite her to go jogging with you.  This might not sound romantic to a non-jogger, but if you’re both avid runners, then it’s a great idea.  Ice-skating and rollerblading are two other great options.  Hiking, biking, and any other sport you can think of will work to get your adrenaline flowing and spark a connection.  Activity dates are a great way of getting to know each other and having fun at the same time. 


  • Creative Dates: Want to do something awesome and show her that you’re different from all the other men she has dated in the past? Then it’s time to think outside the box.  Women love outside-the-box thinkers.  Do something unique; something fun and exciting.  Invite her to an outdoor festival, fair, or concert.  You can visit a local tourist attraction, go on a ghost tour, or invite her to do one of Philly’s famous restaurant/bar hops.  The idea is to do something fun and unique to stand out from the competition. 


Do you want to learn more about dating in Philly?  Are your skills a little outdated or rusty?  Do you need a little matchmaking help?  Let our Philadelphia upscale matchmakers teach you how to approach modern dating and create a lasting impression on the women you go out with.  It’s easy to master the art of modern dating, all it takes is one simple phone call to get started.  Start meeting quality single women in Philadelphia today by filling out the private form on our homepage.