The Old Flame

The First Month: Practice Date

I like to tell a version of the story where I showed up to Portland, walked into a coffee shop and tripped into a relationship. I’m sure that I’ll get a chance to retell that story soon. But there was actually a prelude to the story, where I came out to visit Portland briefly and got into an argument with a guy about Shakespeare. It’s not popular, especially among theatre kids, to talk shit about Shakespeare, so perhaps this is why I do it. It pissed The Old Flame off and an instant bond was formed. We tried dating briefly once I moved here, but he wasn’t quite over his stripper ex-fiancée, and when our clothes came off the sex never happened. Over the years we’ve remained dear friends, and even though we probably only dated for a week, he has honorary title as my ex.

With perfectly sunny weather overhead, we decided to have a picnic in a park, and use his super sleek motorcycle to get there. Hearing my mom’s apprehensive voice in the back of my mind, I took pause to suss out my own level of fear. I’ve had to work on some trust issues when it comes to climbing on boys’ bikes. I briefly dated a guy in high school who really had no idea what he was doing, and I felt lucky to have survived the ride. But in college I went on a few dates with the bouncer of a night club. He was always so sober and responsible that riding with him put a lot of my fears at ease. And The Old Flame is even better than that. He diligently secured a helmet to my head and told me how to position my body. As I wrapped myself around him I wondered for a second if this friend hang-out was starting to feel slightly different from “just friends”.

We rode through the city, our bodies hugging the turns, his speed reasonable and his braking smooth. We arrived at Cathedral Park*, located under the picturesque St. John’s Bridge, and had a yummy picnic in the sun. While laying in the grass and sipping on ciders we caught each other up on our lives. It is so comfortable to be with him. And he’s funny. I hadn’t forgotten that about that, it’s just that all those years ago I remember feeling that he was always preforming. Whereas now he seems to have come into his own. His humor seems effortless.

On the ride home I held him closer. I could feel his heart beating in his chest, and I could tell that he was very aware of my presence as I gripped him with my thighs. When we pulled up to my place we weren’t ready to say goodbye, so we went up to my apartment and lay down on my bed (oops, sorry-not-sorry that I live in a studio and don’t own a couch). He told me that he hadn’t been sure, but now realizes that he does in fact still have feelings for me, and “I don’t want to risk our friendship…but would it be ok if I kissed you?” It was a very long and pleasant kiss. I enjoyed the intimacy immensely, but noticed that there were no butterflies to be seen. There’s obviously still something there between us… I’m just not convinced that it is worth investigating for a second time. We’ve already looked down that road. And honestly, I have this strong desire to only move forward. No falling back on cute and comfortable exes. I really have to just put myself out there! The thought is both exciting and horrifying. I don’t feel ready, but I’m scared that I never will be ready unless I force myself to get out into that big intimidating dating world. Now in my 30’s with 2 failed engagements under my belt, a partially mended broken heart and a bruised ego, I must act braver than I feel! I have no choice but to swipe right, say yes, and go out on a freaking DATE with a STRANGER!

Portland Date Option:
*Picnic in the beautiful Cathedral Park, located under the iconic St. John’s Bridge. The bridge was designed by poet and engineer David B. Steinman and opened in the early 1930s. This seems to be everyone’s favorite Portland bridge, and definitely deserves a visit.

___________________________________________________________________Liked what you just read? This piece is part of a series called Men & Meals: One Woman’s Feast. I’ve challenged myself to 100 dates in a year and I invite you to Follow along!