D8 with the Answerman

The text exchange I experienced with Glen was a lot of fun. He was a very witty and quick thinking high school teacher at a Manhattan private school. History was his subject, and as a favorite of mine, we had lots of potential topics to discuss. The texting was very easy with Glen, and I thought it would be fun to take it to the next level and meet for a coffee, in spite of one red flag.

The history teacher had no history.

At 53, Glen has never had a substantial relationship. No former partners and he never had a boyfriend for longer than, say, six months. He’s never lived with a partner, solved problems with a partner, nor has he gone on vacation with a partner. He’s never raised a pet, nor has he hosted a holiday party with a partner. Is this a deal breaker? I’m not sure. Perhaps he’s been inundated with working on a Masters and focusing on his career. There are lots of possibilities as to why he put his personal life on the backburner. Glen seemed to be very steady in his resolve to commit to a relationship and was excited about creating some history. On that, I decided that sharing a Venti Frappuccino couldn’t hurt.

I met Glen for a coffee in Midtown. The conversation at Starbuck’s was one of the most interesting I’ve ever had on a date, but not in a good way. I could share the entire conversation, however each question I was asked ended in the same fashion. Here’s an idea of what conversing with Glen was like…

“Craig, who’s your favorite college football team?”

“Oh…”, I responded, trying to say Ohio State when Glen’s hand went into the air motioning for me to be quiet.

“My favorite team is Penn State.”

From favorite TV shows to restaurant recommendations, his hand was in the air and my answers were “Frr..”, “Ahh..”, “Eee” and “Buh…”. I reached a point where I thought I was auditioning for a remake of the film Nell, and I was up for the Jodie Foster role.

At first I thought it was sort of funny, but then it became both annoying and illuminating. It explained to me why Glen has no history with men. Who is going to be able to take a steady diet of giving “Ack…” and “Chr….” responses and seeing Glen’s hand in the air all the time? I realized that if I were in a relationship with Glen, he would have the answers to everything from where we are spending the holidays, what we would name our dog, and where we were going on vacation. When it came to problem solving there would be no consensus because Glen is the Answerman.

My breaking point was when Glen asked me where I was from in Ohio. “You tell me, Glen. You tell me,” was the response I gave through a giggle as I finished my Frappuccino.

“What’s so funny?” asked Glen.

“Well, Glen, you haven’t let me answer one question. You shushed me so you could answer your own questions, again and again. Seriously, Glen, what have you learned about me in the last 20 minutes?”

Glen was rather flabbergasted, and perhaps a little embarrassed. He knew I was unfortunately correct in my assessment. I wished the Answerman all the best and was on my way.


My date with Glen took me back to freshman year of high school and my first communications class. I remember Ms. Ganz teaching us the importance of listening. “Listening allows you to learn and empowers you to respond intelligently”. Listening is even more important than speaking, and to that end, you have to allow your communication partner, be it a dating scenario or not, to actually speak.

The best way to discern if your date will lead to a 2ndFineD8 is to really listen to them, and that means allowing them to speak. Learning your date’s likes and dislikes is important, but gauging their sense of humor and intelligence is critical. Is there a sparkle in their eye when they speak? Do you hear a welcoming tone in their voice? Perhaps the combination of both with the words they say are telltale signs that they are flirting with you? You’ll never know the answers if you never allow them to respond.

When you’re on your date, ask your date questions about themselves. Hobbies, career, their Alma Mater, and pets are great places to start. You’ll be able to learn quite a bit, such as if they’re an overall positive person, their sense of humor and their excitement levels on each topic. Let the conversation flow, and enjoy the ride!

I’m not sure if being the Answerman is the real reason why this history teacher has no chapters of relationships past in his own private textbook. Not being able to get a word in edgewise kept me from asking. My hope is that if it plays a role in his lack of success in the dating world, he took my feedback and applied it to his next date.

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