Wingman wisdom… Make the first date a first meet!

Wingman wisdom… Make the first date a first meet!

It’s a match!  Everything has clicked and you are ready to transition from the digital world into the real one.  The pressure is on to figure out the where, when and what to do!  Planning the first date is challenging!  Especially when you are moving from online to off.  You really don’t know all that much about the person.  I mean come on…how much insight can you really have from a weeks worth of sharing photos, texts and maybe even a brief phone call.  With so little insight into your “match” how the hell do you plan a great first date?  In my expert wingman opinion, you don’t!  Don’t even think about it till after the first meet!


Changing “date” to “meet”!

It’s estimated that online daters spends on average $20k on dating related expenses within a five year span.  Now imagine how much time and effort is also exhausted!  Whoa, Right!  Unfortunately, the modern digital dating scene is really tough.  It’s riddled with fakes, scammers, and ill-intentioned folks misrepresenting themselves in all ways.  This often leads to one bad date after another.  Ultimately leading to a great amount of disappointment!  So, what’s the best way to take your connection offline?

After years of experience I found a very simple and effective solution; the “first meet” rule!  This simple rule will change your entire dating experience!  First, simply substitute “meet” for “date.”  This immediately lowers expectations to a more reasonable level.  Next, change your mind set to be more connection focused.  Think of it like this… before you can make a real first date doesn’t it make sense to see if there is an in-person connection!  Finally, get rid of all the pressure!  The connotation of “date” is so damn rigid and formal.  So to alleviate all pressure it’s best to simplify the first get together entirely.

Every “first meet” should be casual, simple, and light.  This allows for both parties to be me comfortable and to just be yourselves.  To really make your “first meets” great follow these simple rules…

Wingman Tips Rules

  1. Keep it casual!  You are not walking down the aisle just yet in a tux or gown.  It’s just a first meeting and no need for unnecessary pressures.  For example make plans to meet up at low key coffee shop where you can spend some time chatting.  Yes, it is a bit cliche.  However it is a highly effective!    A huge plus here – it’s much easier to leave a bad first meet than an extravagant dinner date.  
  2. Set a maximum time!  Keep the meeting to an hour max.  Mention this prior to meeting so that there is no misunderstanding.  An hour is ample time to make a first impression and to know if the potential exists for a future romantic connection.  Best perk is this minimizes the max time on bad first meets.  
  3. No pressure mindset!  Knowing you are only meeting the person versus having a date should remove all unnecessary pressures.  This makes it easier for you to just be yourself and enjoy the time getting to know one another.  Maybe you will find a new friend or maybe it’s time to plan a romantic date.  Just go with what feels right!

There are couple primary benefits to “first meet” rule.  First, if there is no connection it’s super easy to move past all negative experiences.  Most important, if you do hit it off, it is a lot more fun and easier to plan a romantic first date.


My Personal Experience

This advice comes directly from my own personal experiences.  During the time I was creating hey there… dating app I was very active on the dating scene.  Date after date without any romantic connection.  I was getting extremely frustrated with lack of results.  So much so that I began questioning online dating all together.  I knew I had to do something to make it into the fun experience it was intended to be. So I created the “first meet” rule!   It immediately had a profound effect on my dating life.  I started having fun meeting people again.  I was less concerned about results and more happy to have the opportunity to meet new people. I made many new friends as a result.  Ultimately, I ended up meeting one amazing woman!  It all started with a simple meet up over a coffee at Starbucks.  We instantly hit it off and couldn’t wait to see each other again.  We planned a romantic date soon there after.  Many dates later we are still together and looking forward to a future together.  We often look back at our first meeting and try to encourage others to take the same positive approach we had that day.  No pressure, carefree, and just enjoying the opportunity to meet someone new with the potential for romantic connection.  There is an old saying that goes something like…  “it’s not where you are that matters but rather who you’re with that does.”  In essence that is the meaning of the “first meet!”   Dating can be so damn complicated.  In my opinion there is no need to make it even more complicated with unnecessary pressures of grandiose first dates.  The connection is with the who ….not the where, when, or what!


Just be real from the start!

Recently a really good question about a very common issue for many online daters was asked in the Hey There New England Singles Group on Facebook (

Donn: ”How many times have y’all been on a few dates everything seems great then bam! They flip a switch and are like a completely different person…. Just be real from the start!! I can’t stand that sh@#. I will leave regardless because to me you played me!”

Unfortunately for our friend Donn, he experienced the online dating bait and switch. Everything is going well for a hot minute then suddenly everything changes drastically. That amazing person you were all excited for turns out to be someone totally different. Did you just meet Dr. Jekyll Mr. Hyde? The truth is that online dating makes it very challenging to just be yourself.

The Bait

The goal of every online dater is to advertise themselves as a great catch. In this attempt to portray themselves in the best possible light, the tendency is to create a profile based on what we think other people find attractive. Creating false identities and personas online is extremely easy to do. A person can pretend to be anyone they want to be. The most common fabrications online daters make are personality, physical appearance, careers, and financial status. Use the right “bait” and attract that trophy fish. Every exaggeration is in an attempt to become the most desirable candidate on the market. White lies in regards to height and weight are usually forgiving by most. But when it comes to personality and character not so much!

The Switch

Most people are not blessed with the necessary acting skills to keep up with their fabrications. Sooner or later the switch happens revealing their true self. It totally catches you off guard leaving you ask… Am I talking to the same person? What the hell just happened?

The switch happens quickly. Just like what happened with our friend Jenn from the group.

Jenn: “I had that happen recently with someone. He came back from his business trip in LA and was a completely different person then I had been led to believe.”

No one likes to be led on. It hurts! It’s a total waste of time and energy! Worst of all, it makes it difficult to not be guarded in the future! Is it so hard to just be yourself?

Creating a false persona is easy. Keeping that persona up is the hard part. The best remedy here is to just be yourself at all costs. People appreciate REAL! Our friend Donn from the group said it best…”just be real from the start!” You may think people want a certain type of person but reality is people appreciate honesty and realness more than anything.

Before hopping back on your favorite dating app. Take a few moments to ask yourself these 2 questions.
Am I truly being myself? Remember, we are all unique in our own ways. You don’t have to pretend to be someone you are not. Anyone deserving of your time and company will appreciate you for you are, not for who you pretend to be. And do you really want to keep up a fake profile in real life for who knows how long? No.. so don’t do it to start with.
Am I being completely honest with prospective candidates? Make sure all the info you add to your profile is legit. No one wants to find out later on that you lied about your love for animals. Make sure that your intentions are realistic. If you are looking for a hookup don’t lie and say you want a long-term thing. Better to be candid about yourself in all ways! Makes it much easier to find someone that you will be compatible with.

Keep in mind these 3 tips for success!

1. Keep one eye open, one eye closed. Being a little guarded is ok and can spare you from some unnecessary hurt. Always keep one eye open to be able to pick out the deceptive candidates. But you also need to keep one eye closed to be able to take chances in order to find the “one! You never know who’s going to walk around that corner next.

2. Ask friends to help out. It’s always a good idea to have an extra set of eyes looking out for you. Friends are more likely to keep it real and call BS. They can also keep us honest in what we say about ourselves.

3. Most importantly just be real from the start! When you can truly be yourself around someone then you know you found the perfect match 🙂


The Hey There… Wingman

Staying safe when online dating…

Hey There… 2017

With online dating season now in full swing it’s important to be a little cautious as the potential for danger lurks around every corner.  Scams are on the rise costing online daters more than just a broken heart.  Scams cost singles hundreds of millions of dollars every year.  But the hardships of online dating are not reserved for just criminal scammers.  Many online daters fall prey to serial daters that break hearts at every click.

A great article in the Chicago Tribune from Jackie Pilossoph describes an experience with one of her online dating friends and offers some great tips for staying safe.  

Pilossoph offers these valuable insights into online dating to protect your heart and well being…

“1. Be Mindful When Posting Pictures: Online dating means exposing your photos to thousands of men and women you know nothing about. So, while people always want to show off their children and express how much they love being a parent, it’s not worth strangers seeing the photos. Once you have met the person a few times and trust him or her, that’s when showing photos of your kids is great.

2. Talk to the person on the phone before meeting. Also, meet in a public place where you feel comfortable and take your own car.

3. Do a Google search and Google image search. These days, it’s so easy to check someone out yourself. Once you know the person’s last name, start with a Google Image search. You can learn a lot, most notably, if the person is assuming someone else’s identity or is pretending to be someone else (also known as “catfishing.”)

4. Don’t put your last name, your address or where you work on dating apps.

5. Use Facebook referrals. In other words, if you see that the two of you have mutual friends on Facebook, reach out to those people and ask about him or her.

6. Don’t use your regular cellphone or home phone. Instead, you can use a Google Voice account, which is a free service that you can easily sign up for at no charge. If you want to go a step further, there is a new app called Burner, which is a phone number that disappears if you choose to no longer allow this person to contact you.

7. Don’t share and check in where you are going on Facebook. Instead, post pictures when you get home. There is no need for anyone to know that you aren’t at home, especially someone you might have dated where the relationship ended badly.

8. Don’t spend too much time in a texting/phone relationship. After a few conversations or a couple weeks at the most, move it offline or move on to someone else.

9. Expect that you will meet people who disappear for no reason. It’s hard not to take things personally when dating, so if someone stops responding or is suddenly not on the app anymore, assume he or she either got back together with someone else or met someone special and decided to be exclusive. We would all like to hope that someone would give us an explanation, but that usually doesn’t happen. Try to move on and realize it was most likely nothing you said or did.”

No matter how experienced you are online always remember the hearts desire to find companionship and love can be blind to the dangers that await online.  It’s always great practice to keep a level head.  Whether you are online or off in pursuit of love always keep one eye open to guard against hurt, while keeping on eye closed to take a chance on the unknown.  Stay safe and best of love this 2017!

Full article from Jackie Pilossoph: