Dish Collective

Men

THE KNOW IT ALL

Dating, Men, AdventuresJen gurveyComment

Being single in your 40s has proven to be quite the challenge. My belief is not because of the city in which I live, but because women have choices, a lot of them especially if they're single.  With a little research, they are exposed to a plethora of online matchmaking sites promising everything from taking long walks on the beach to paying you monthly allowances.

Meet Dan Smith.

His profile, sparse as it was, revealed two nice looking photos, clean cut, local-ish to the Bay Area, assuming San Jose is still considered within the realm, and he seemed to be looking for the usual chemistry, connection and something more.

We email each other 24 hours before planning our meeting, and he shares his name is actually Robb. OK, hello Robb. The email banter is short. No flirting, little information exchanged and more firm in tone than I typically experience. My excitement level was low, and relieved that I had another drink appointment lined up shortly thereafter. I’ve learned over the years that having an escape plan is always a smart idea.

I arrive 5 minutes late to the empty bar where we’ve decided to meet. He’s seated along the wall at a communal table, vodka drink nearly gone and somewhat attractive. Not sure he looked like his photos, or at least the primary one that was probably taken some 10 years ago and 20 pounds lighter. He barely greets me, picks his head up from being buried in his phone and says, “Oh, hey! You know sign language?” Shocked as I was that he greeted me with some historical information, it was creepy that within a few minutes of finding out my last name (TIP: be sure to create a fake email account, name and cell phone number!), he was now studying my LinkedIn profile. I smiled, gave him what I refer to as a fake laugh and asked if was looking for someone in marketing. I mean, play Words with Friends or something other than researching the date that’s walking through the door.

I’d like to say that the conversation flowed but in all honesty, there was very little in the way of conversing. He spoke to me and at me. In fact, it took Dear Robb a good 15-20 minutes to not only ask me a question but then every so often, he realized that I too may want a drink. I think I politely mentioned my drink preference about 4 times as he continued to steam roll over every topic he could cover, all in one breath. Barely able to keep up, it ran the gamut from all of his “successful” dating experiences, to his awesome ex-girlfriend who lived in the Marina and worked at Goldman Sachs to the fact that I had far too much competition within my age category to even consider dating anyone under the age of 60. Almost aghast, gulping down my newfound love for Mezcal, I not so subtly laughed out loud thinking I was on candid camera. Oh, I can’t forget his oh so bold, right winged political opinions, back to sign language to him buried in his phone again texting with whom he refers to as “cat sitter.” Cue fake smile as he begins swiping his photo album to share the handful of his 17 year old cat photos. Sadly I couldn’t even get a word in to tell him I wasn’t a cat person. Forty-five minutes go by and I was exhausted. This so called conversation felt like a surreal Ping Pong match gone wrong. As he continued to talk to me, about what I can’t recall, I thought my meter should be running out soon and it was my perfect excuse to wrap this up. He looked up again, noticing my empty drink, and asked, “Another one?” I flashed him my no so innocent smile and politely declined. “Ya know, I’m all set. I think I’m done here,” I said. He agreed, paid the bill and off we went. Walking a good five feet apart, down the sidewalk of Market Street, making not so small talk, he got to his car first. “See ya.” Wow, one more drink appointment under the belt and I’m pooped!