Interesting people, places, conversations, experiences & insights brought to you by a guy who uses the Ride-Sharing platform to Life Coach his passengers.


February 13, 2018
With Valentine’s Day now here, I felt it was time to discuss an idea I have had floating around in my head for a while… UBER dating! Hey, why not? Uber has moved into other experimental service areas like food & package delivery, transportation by water & air, automated cars, ice cream to the office, roses to women on V-Day and even delivering puppy therapy to the workplace, so why not Uber dating?
OK, OK so I have to be honest here and tell you that I couldn’t write about dating “Uber-style” unless I actually tried it myself, and that I did. It was not planned, I only remember I picked up a couple and another woman who were all coming from the Boston Symphony one Thursday afternoon. We had a very engaging conversation and many laughs along the way.  The woman was single and she must have asked for my business card, but honestly I don’t remember. Two days later I received an email from this woman (let’s call her Donna). Donna apologized for reaching out to me and for her reasoning to do so… which was to ask me out on a date. 
Being a guy that loves adventure, all kinds of adventure, of course I had to accept (little did I know it would provide future content for my blog). I didn’t even remember what she looked like, but she wanted to meet close to her apartment in Brookline and picked out a restaurant on Beacon Street. For the record, I never would ask a passenger out and although I have many meaningful conversations with them, I always keep it professional!
I hardly recognized Donna when she arrived, as she looked like she just got off a Harley, wearing all black with big black lace-up boots & a leather jacket. This was a complete 180 from her previous ultra conservative look. The date started out well and we were only supposed to have a cocktail or two.  When she started ordering $20 Scotches and telling me how her deceased husband left her with lots of debt and how she has an ongoing intimate, physical relationship with a guy with Asperger Syndrome… I am not really one who judges others, but I just knew this date was headed toward disaster.  On top of all this, Donna had to be one of the most negative people I have ever encountered. As you might expect… there was no second date.
Just because Uber dating did not work out for me, it does not mean it won’t work for others. My idea is centered around the shared ride service called “Pool,” where the driver sporadically picks up people heading in the same direction.  Why not have a weekend day where you only pick up pool riders who are a match for what they are looking to date, and see if the conversation ignites any dating interest?  Good idea, right?  The only catch is you have to have a driver who can be that conversation catalyst to get things going… you know like, “Hey, you guys both have blonde hair…what a coincidence?” or “WOW, you guys work at the same company, she’s not your boss is she?” It could be a little awkward and I am sure there is some kind of liability that would forbid Uber to offer this kind of service.
I remember discussing this idea with a young professional woman a while back.  She was the first rider in the pool.  She loved the idea and as it turned out we were picking up a guy along the way. We laughed at the prospect of her dating this guy and I told her to keep an open mind cause ya never really know. Imagine actually meeting someone organically and not from one of those online dating services! Long story short, I never mentioned the Uber dating idea to the guy, and rather let things progress naturally (well, with a little help from me). The conversation went well and the guy got dropped off first.  She worked in Bio-tech and he was an entrepreneur working at a start-up so it seemed like an interesting match.  I asked the woman what she thought and she mentioned that he was very cute with a nice personality, but he looked like a metro-sexual.  I asked, “So that’s a good thing right?” Apparently not, as she finds most metro-sexuals a little on the feminine side!
For now, my Uber dating will remain a work in progress as I go back to the drawing board to re-think this whole idea! In the meantime, HAPPY VALENTINE’S DAY!
  1. Reply


    December 29, 2018

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  2. Reply


    December 29, 2018

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Greater Boston, MA

Long story short: I started with UBER (5) years ago as a sabbatical from enterprise B2B sales. I have found driving for Uber in Boston to be one of the most engaging gigs I have ever experienced. SOOOO… I decided not to return to corporate life and use Ubering as a platform to help people through life coaching, conversations and random acts of kindness. I am a very HAPPY camper now!

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