Interesting people, places, conversations, experiences & insights brought to you by a guy, who took some time off from corporate enterprise sales to take an Uber sabbatical... and that sabbatical continues 4 years later!
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
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!