Getting Around Town With Jamie Shupak: A Year of Lessons

Getting Around Town With Jamie Shupak: A Year of Lessons

In 365 days I went on about 30 first dates and politely described about a third of them here, in this column. I sent about 10,000 text messages (don’t worry, Dad—unlimited plan!), but published only 20 or so. I drank plenty of tequila gimlets and fired off 25 “this isn’t going to work” emails, though I only shared two or three publicly.

I didn’t set out to teach or advise; that was never my goal. I wasn’t out to find a boyfriend either; nope, I didn’t want one of those. I wanted to have fun. I wanted to meet new people. I was given a rare golden ticket to start over, to figure out what I liked and didn’t, and then share what I saw, heard, and felt so you could better understand the intricacies of dating, right along with me.

I began my first column last March as I began life as a Single Lady, armed with what I still consider the best piece of advice. My Dad told me to pretend that I was driving without a rear-view mirror, and that’s exactly what I did. I never looked back. Until now, that is.

It’s time to see what we learned this year.

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The first guy I dated seemed intelligent enough, based on his career path, anyway. But our text conversations—never a phone call, no—usually looked like this:

Him: Wut r u up to 2nite?

Me: Going to dinner with my girls, then not sure. How about you?

Him: o that’s tight. Wherez din? U should hit me up after.

So, that wasn’t going to work. I wanted a guy who would type and talk in full English sentences, like an adult. I use plenty of shorthand in texting—everyone does—but if you peek at my phone you would never confuse what you saw with a teenager’s conversations.

Next.

A few months later I went on a great first date. What I liked about this guy was that he not only asked me really thoughtful questions—a lot of guys can drum up interesting inquiries—but that he was genuinely interested in my responses. He looked me in the eye, intent on learning what made me tick, what people get wrong about me, and why my last relationship failed. Some of this seemed a bit personal, a bit forward of him, but his genuine charm made it work.

I learned that it’s okay to let your guard down sometimes, to not be ashamed of your dating history, and that when you make the woman feel comfortable, she might really open up to you.

Onwards.

You all remember the guy I was supposed to meet for drinks at 7, who texted me at 7:05 saying he was going to be fifteen minutes late?

That wasn’t going to work either. I wrote about the importance of being on time maybe one too many times. But I think it’s important to be with someone who respects your time as much as their own.

Moving right along.

I dated another guy who you could file under "Bring Home to Mom". In fact, my mom did meet him when she was visiting me in New York, and loved him. He’s the kind of guy who pays attention when she’s talking, then smiles and gives her the “Aw, Mom” as he puts his arm around her. It was endearing, not slimy.

We went out a bunch of times and even though he was family-approved, I wasn’t ready to commit when he asked that we date exclusively. I hadn’t been single six months, and like a dog who’s been cooped up inside all day then gets to run free when its owner gets home, I was still enjoying my new-found freedom. I broke his heart when I told him. He said if he were the right guy timing wouldn’t matter; I disagree. You have to be ready and willing to be in a relationship; at the time, I was neither. He was the first guy I dated consistently, so I knew I had more to explore in both myself and other guys.

I also learned it’s best to be honest if you want to preserve both your relationship and reputation. We’re still friends today.

That’s not the case with this next guy, but I learned that sometimes that’s okay too.

I realized after hanging out with him a few times that he only texted me late at night, and never asked me earlier than Friday what I was doing on Friday. I was a bit (mistakenly) enthralled by his older, hot guy mystique, so I always responded and met up with him.

It didn’t take long until I was turned off by his laziness and inability to make a plan or reservation. I learned that what you tolerate and the behaviors you enable are exactly what you will get in return.

If you respond to a guy’s texts at 1 a.m., you are telling him that’s acceptable, and he will continue to text you at 1 a.m.

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Looking in that rearview mirror, I don’t regret any of those texts, as misguided as some of them were. I had my fair share of missteps this year, and perhaps you have too. That’s okay, so long as we don’t make the same mistakes again.

I think we’ve come a long way together since last March. I’ve written 44 columns and kissed about half as many boys. I learned that some will open the door to a restaurant or car for you and others will open the door to a better life. The best are the ones who do both.

Talk about lessons learned.

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