Dating and How Men Get it Wrong...

I recently had a conversation with a handsome guy whilst at SXSW about online dating. As someone who was married long before digital dating started, I am admittedly a bit removed from the millennial road rules of hook-ups and shagging. 

Said "cute guy" began to explain to me all about the way in which he was connecting with some of the women he bonded with on Tinder, Zoosk, etc. As cute as he was, I wondered why he couldn't just pull the ladies in person. 

He showed me a few photos of the girls he'd connected with...and a few of these he'd actually managed to get their digits. He seemed incredibly pleased with the number of girls phone numbers he had in his phone. 

I had to ask...

"If you have that many cute girls numbers in your phone, what the heck are you doing sitting here talking to me? Why aren't you busy every night and twice on Saturdays?"

He leaned into me, and whispered in my ear that whilst he was really good at writing a decent profile and starting the live banter in Tinder chat, once off the platform his game wasn't so great. This piqued my curiosity. I wanted to know his exact approach...fascinated by what these young folks have to do to get a date. 

He showed me a few of the text messages and DMs he'd been sending. 


"U busy?"

"Wanna hang out?"

or...or my personal favorite...


 Seems Cute Boy committed the foreplay sin of inducing boredom. This guy was a real spunk and twenty years ago I would have been supremely keen. He was well groomed, smelled nice, and knew how to wear a American Apparel t-shirt that flattered him.  He needed to read this blog post about how to turn a girl off

Then I asked him a tough question...

"What's your closing ratio like?"

Seems uber cute boy had a less than .001 success rate with his thumbs. 

I remembered a conversation that I had with a "digital date guru." 

My friend Race in the US - guilty of sending over 7000 texts and a self-professed JEDI on using his thumbs to do the hard yards when it comes to hook-ups - told me that most guys' game drops because they can't seem to engage a girl's curiosity and stroke their sensibilities.

Seems Cute Boy and Race should be throwing back the Titos & Sodas instead of he and I. (Race is so sweet he shares some of his tactics on the internet. 

Watch RACE do his thing LIVE on a video -- it blew me away.

I could not believe that someone so sweet was getting this so wrong. So for him and all the guys like him, I have decided to write a Digital Dating a 101 course at Harvard. I hate to think of how many of these nice boys just can't seem to communicate effectively in text. I can't quite call it an NGO, but it is a bit of a giving back. Here is the first part of the giving - a free guide to become a dating text JEDI -- compliments of Race

I started a blog to curate some of the content for this upcoming book. If you are curious about my tips for Digital Dating click here. If you've got a question on Digital Dating or a golden tip I need to include in my book, or would like to be interviewed for my book, send me a message. (my firstnamelastname @ Gmail.) 

Meanwhile....stay positive, productive and motivated!