If I could, I'd run a piece from Caitlin Bergh every day on here. So few local performers work with such a well developed voice; her self-effacing, reflective style is unrivaled here in Chicago. Caitlin was nice enough to send over this story to run in advance of her new one woman show, CHUNKS, which can be seen every Sunday this month at Studio Be. Tickets links and more information about the show can be found . 

When it comes to relationships with women, I don’t think any word describes me better than “desperate.” Because I’ve been out now for about 4 years, my desperation has significantly decreased. But during my first few years of finally knowing what gender I wanted to date, my desperation around beautiful women was palpable on my skin like a heavy perfume.

My initial desperation is perfectly encapsulated by a very strange night I spent with the first girl I casually dated, who I will call Anna. I was really, really into Anna. Why? I had just come out, been rejected by the “love of my life” (the girl I came out for), and was now, for the first time, desperately looking to date other girls. Anna happened to be the first girl in my tracks.

Anna knew that I was into her, and she was both scared and excited. The first time we hung out, she told me she had just gotten out of a bad relationship. But all I heard was, “hey I’m beautiful, you should pursue me.” The second time we hung out, she told me she needed to be alone because she was trying to figure out whether she wanted to date men or women. But all I heard was “I’m open to dating women. Also, I’m still beautiful.” The third time we hung out, we decided to go out “cruising for chicks” together. Of course, all I wanted to cruise for was her.

We went to Berlin nightclub and Anna challenged me to get three numbers. I agreed. We started drinking and dancing until, several hours later, she realized I hadn’t gotten any numbers and jokingly got mad at me for it. “Honestly,” I said, “it’s hard for me to be interested in these girls when you’re here, and I’d so much rather be getting a number from you.” By number, of course, I really meant amazing sex, lifelong commitment, maybe a few kids and a dog.

Anna looked surprised and walked over to the bar without saying anything. Then she came back and said “Caitlin, I feel the same way.” She put her hand on my hip and pushed me into the wall of Berlin, forcing my exposed back into contact with about 8 million STDs. But I didn’t care if I got back chlamydia, because she kissed me. It was the best kiss of my life.

Anna took me home that night and we made out dramatically on her bed.

We started going on dates regularly, always ending with dramatic make-out sessions on her bed. It was too good to be true. Really. Because soon I found out that I was not the only one coming home with her every other night. So was a guy named Jon.

As it turned out, Anna was figuring out if she wanted to date men or women by dating one of each of us for a “trial period.” Kind of like Netflix. I knew there was no way I could compete with Jon. He wasn’t better; we were just different. We had different body parts, different personalities. I couldn’t compete with an MBA student with a dick, and I didn’t want to.

If I had had any self-respect, I would have told Anna that I needed to know which of us she wanted before it went any further and I got hurt. But I just wanted to keep making out with her. Dramatically. One night we came home to her apartment to find roses from Jon, and it was just too painful. I told her I wanted to be with her. She told me she was ending it with both Jon and me, because she still couldn’t figure out what she wanted. I was devastated. I sobbed uncontrollably in a public restroom.

A few nights later Anna called me from a bar and asked me to come out. Maybe this was it! She had had her space (a few nights) and had picked me! I dressed cute and went to see her. We had a few drinks and she invited me home.

We got to her apartment and I started to kiss her. “Stop!” she said. “What?” I asked, “isn’t this why you invited me over?” “No,” she said, “I just didn’t want you walking home alone so late. I still need space Caitlin. I can’t make out with you or Jon.” “So, you want me to just sleep on the couch?” I asked. “No,” she said, hugging me, “sleep in bed with me.” My head was about to explode from all the mixed signals.

In bed, she grabbed me and started kissing me again. Then she pulled herself away and said, “I can’t! I need to take time.” Then she did something unbelievable. She grabbed her retainers off of the nightstand and aggressively put them in her mouth. “There,” she said, lisping, “now I can’t kiss you.” “Are you telling me,” I asked, “that you brought me home, invited me into your bed, started kissing me, and then put your retainers in to keep YOURSELF away from ME?” “Yes,” she said with a lisp. I was in shock. No one had ever tried to repulse me with orthodontia before; it was beyond insulting.

“Anna, good luck,” I said, getting my stuff. “One last kiss?” she asked, gesturing that she could remove the retainers. I leaned in and kissed her without even thinking. The feeling of someone’s retainers on your tongue with the knowledge that she put them there to keep herself away from you—that’s what it feels like to be desperate.

-Caitlin Bergh

Note: This story was originally published in Rebellious magazine and is reproduced here with permission. You can find the original here.