I have to start this week’s post with a shout out.  I had a big Housewarming Party this past Saturday, and it was a “Haunted” housewarming aka a Halloween Party.  It was an incredible time.  We had an amazing amount of creative costumes, but the talk of the party was the Dating By Wegs group.  My friends who read this blog dressed up as the various blog posts – Swim Date, Kenosha Truck Driver (very loose interpretation), my military Catfish/Crazy person, and my personal favorite – my doppelganger – Dad Jeans.  Thank you everyone for both celebrating my new beginnings and poking a little fun at Wegs.

Dating By Wegs

Rule #6 – Have Fun!!

We have gone over a lot of rules to navigate this world of dating.  However, one of the key things to keep in mind (and maybe should have been Rule #1), is to have fun.  I think a simple question can be asked every time you go out with someone new or even someone for the 3rd of 4th time – “Am I having fun?”  Or “Am I enjoying myself?”  I’ve been in 2 marriages now, so trust me, I know the negative side to relationships.  I remember a good friend of mine telling me several times when I was struggling in my last marriage the old adage, “Life is too short.”  I completely agree.  There is no point to toiling away at life and not stopping to laugh out loud or do something totally exhilarating with someone else.  I think in rediscovering myself in this whole thing, I realized that life gets a hell of a lot easier when you have something to look forward to and when you get there really enjoying yourself.  The bottom line is tomorrow is not guaranteed, so make the most of the time you spend with people.

Wegs, that sounds great, but how do you do this, though?  I may have said this before, but having fun starts with you.  As a single person, naturally, we get exposed to more things, so being open to those things is an attitude that really helps having fun.  As I said in Rule #1, being creative on dates is about you being pro-active in finding activities that you or your date have never tried.  Taking chances to put yourself out there may be scary, but finding a cool new spot or fun activity breaks the boundaries down with your date.  Plus, you gain extra points on breaking the mold.  The other side to starting with you is that when something doesn’t go well on a date or the idea you float is not received with the excitement you expect, then find something else.  Be flexible and open to something your date may want to do.  It’s not all about what you want to do all the time.  You may be surprised by an activity your date wants to try.  The absolute most important thing is to make the most of the moment you are in – Stay Present – each experience you have is valuable, even if you don’t find your complete match.

2 approaches to fun dates:

With Competition Everyone Wins:  I’m a firm believer in competition.  Everyone who knows me will attest that I’m a competitive guy.  In doing competitive activities, both people typically will give their best efforts as not to be embarrassed.  More importantly, if you can find that good level of competitive spirit, that tension can really lead to some fun and memorable dates.  Here are some competitive date ideas I’ve been partaking in over the past few months:

  • Swim Date – Yeah, that was a new level of crazy.  However, it was so fun and memorable.
  • Shuffleboard – That’s right, the old timer activity.  There is a push to do old time activities in our cities.  Here is the spot I went to with a date and really recommend:  https://www.royalpalmschicago.com/
  • Darts – There is a cool dart parlor I have not tried yet, but I have met a few ladies at the bar playing regardless of skill level.  Here is the spot on my list:  http://us.flightclubdarts.com/chicago/
  • Ax Throwing – I haven’t tried this one, but it is definitely on the list.  https://batlgrounds.com/

Exhilarating Activities:  I think that you may be seeing a theme here.  I have a bit of a theory that I’m working on.  Adrenaline during dates can lead to deeper connections.  I’ll have to let you know if that is actually true.  However, in a competitive situation, all those endorphins are flowing with the physical activity and competitive environment.  The other way to go about that without actually competing is to check out exciting events.  I like music, but I’m not a huge concert guy.  However, I think the same effect can be achieved with really good music.  For me, it comes in the form of the Circus lately.  Here are options I’ve been doing, too.

  • Midnight Circus – The Midnight Circus is a local Chicago circus done in the Chicago Parks from the end of August to the end of October.  There is really nothing like seeing humans doing things that defy logic and imagination.  https://www.midnightcircus.net/
  • CirColombia – I found this one in a What To Do search for a date last week.  This one was part dance, part circus.  Really entertaining.  http://circolombia.com/
  • UniverSoul Circus – This circus has been around a while now, but I have yet to see it.  In fact, my initial suggestion for the CirColombia date was to see Universoul Circus.  I’ll check it out soon.  https://www.universoulcircus.com/

                                                                                                                                       (I promise this wasn’t me.)

This week’s story has to do with a simple childhood game.  Ping Pong.  So, as I said in my first post, Hinge has been a really good app for me.  I’ve enjoyed how the interface works to connect with people.  As I wrote before, Hinge gives you both pictures and provocative statements to open the conversation.  To me, this is genius and exactly what I need to figure out how to get things moving.  So, after reviewing several profiles, I came upon a pretty woman who wrote in The Dorkiest Thing About Me Is….”I secretly love to play ping pong.”  A bit of background…

My parents were divorced in my teens, and when my dad relocated a 2nd time post divorce to the Denver area, he bought a ping pong table.  I mean come on, who wouldn’t love a ping pong table in the garage, right?  I have fond memories of playing with and against my brother back then.  I wasn’t Forest Gump or anything, but I could play.  Then, going to college at Colorado State, in my 2nd year, I was an RA at Newsom Hall.  Those first 2 weeks of the school year we had a mini ping pong tournament.  I reached the finals and played this dude, Gill, who literally had one hand or truth, one functional hand.  His 2nd hand he had an accident or birth defect or something, which honestly made him all the better at ping pong.  This guy would toss the ball up in the same hand as the paddle for a wicked spinner serve.  I vividly remember an epic battle with Gill in the finals which was something of Newsom lore.  Of course, he beat me, but I can safely say I was good.

Fast forward to this Hinge ad, I simply commented – “Ping pong, huh?  We should play.”  She was game, and of course, in Chicago there is a deluxe ping pong bar called Ace Bounce –  https://www.acebounce.com/  I found the place online, and I knew it was the spot.  Ace Bounce is off the chain.  I walked in on a Thursday evening, and the place was bumpin’ with a DJ, like 12 ping pong tables with balls flying everywhere, and even beer pong tables.  This place has it down.  You get a bucket of balls and 2 paddles, pay too much for an hour at the table ($40), but as you play, you just let the ball stay on the ground and there are employees scooping up balls and refilling the bucket at all times.  It’s quite a scene.

I met my date at the bar, as we had about an hour before our table reservation.  I was enthralled by her, as she was a tall, beautiful woman.  We grabbed a spot at the bar and got a couple of cocktails.  The whole scene was energizing with the music and the place was dripping with fun.  So, I really enjoyed our conversation about all things.  She is from NYC.  I learned that she had recently picked up ping pong at her job.  At her firm, there is a table that people play on breaks and often.  I knew I was in for a competitive game.  We got our paddles and bucket and headed to the table.

We started with a little warm up.  I mean I hadn’t picked up a paddle in over 20 years.  It was clear she was skilled and so I had to get back up to speed quickly.  I think I lost the first 5 points on serve.  Thankfully, as my competitive spirit kicked in, I was able to handle her heavy, low trajectory ball.  In time, I was jumping from side to side on this table and was able to win the first game.  I think she was a little upset, but she assured me that she was having a good time.

We ended up playing like 7 games in the hour.  I gotta be honest, it was so much fun.  She was really good, and even though I won more of the games, every point was quality.  Again, the whole scene was something, and for me, having that competitive tension for a full hour was totally exhilarating.  She did win the last 2 games, including the “Winner Take All” final game.  We finished up and chatted a bit more.  I told her that I really wanted to see her again.  I thought we had made a real connection – of course in the glow of all that adrenaline.

Of course, in typical Wegs fashion, I haven’t heard from her since the following day.  I will reach out to her again soon, as maybe she got busy, plus following Rule #5 – Abundance Principle – I don’t want to get too tied up in her.  Although, I don’t think I was alone in enjoying the evening so much.  I do hope to see her again, for real.  The important thing is I had a great frigging time.  I tried a new venue, played a game I used to love, and connected with someone in the moment.

So all of you daters out there, find your way to have fun one bounce at a time.

Wegs