by: Caitlin Bergh 

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 who I wanted to date, my desperation around beautiful women was palpable on my skin like a heavy perfume.

Nothing better encapsulates my initial desperation than a very strange night I spent with the first girl I casually dated. To protect her identity, which is somewhere out there in the world not talking to me, I’ll call her Anna. For some reason, totally unknown to me and everyone around me, I was really, really into Anna. From the first day I met her, I just couldn’t think about anything else. The reason I was into her, which I mentioned was “totally” unknown back then, is now, in hindsight kind of known. I think it was because 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, looking to date other girls. Anna was the first girl in my tracks (#desperate).

If a person who just came out of the closet meets you and falls in love with you, you are very lucky; you also better watch the fuck out. Cause he or she will stop at nothing, I mean nothing, to marry you as quickly as possible. There is no one more desperate than a person who has just stepped out of the deep, dank closet of homophobic shame.

This girl Anna knew that I was into her, and she was definitely a little 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 figuring out that she was bisexual and needed space to think about whether she wanted to date men or women. But all I heard was “I’m open to dating women. Also, I’m still beautiful.” On our third hang out, we decided to go out “cruising for chicks” together. Of course, all I wanted was to cruise for her.

We went to Berlin nightclub and we got Berlin bombs (Redbull and some kind of flavored alcohol). We stood in the corner together scoping out the 5 or 6 women who were there; they were high out of their minds and dancing in circles around each other. “Hey,” Anna said, “I would love to see you get at least 3 numbers tonight.” It was definitely a challenge, and a pretty serious one, as there were only 5 or 6 women in the room. “Absolutely,” I said, cool as a cucumber. I started talking to one girl, then went back to hang with Anna. “Did you get her number?” she asked. “No,” I said, “I wasn’t interested.” I repeated this six times over the next two hours. Several Berlin bombs later, Anna was frustrated.  “Caitlin, you said you’d get three numbers. You have zero.” I looked at her. It was now or never. “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 meant really 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 over with a new drink. “Caitlin,” she said, “I feel the same way.” She put her free 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 her lips were so close to mine. I leaned forward and kissed her. It was the best kiss of my life.

Anna took me home with her that night and we made out in her queen-size bed. She told me she didn’t want to go any further until we were going  “steady.” “Hold me,” she said. So I did. “Don’t touch my boobs, Caitlin. I said no more stuff until we are seriously dating.” “Oh sorry,” I said, “where exactly do you want me to hold? They are just kind of like at the same height as my arms…” “Hold me around my stomach,” she said. I couldn’t sleep.

The next few times that Anna and I went out ended the same way. Always amazing make out sessions in her bed ending in me holding only her stomach. It was awful. Why was she doing this? Then I found out that I was not the only one coming home with her every other night. So was a guy she was dating, named Jon.

As it turned out, Anna was “taking space” to figure out if she wanted to date men or women by dating one of each of us for a “trial period” before making her decision. This was very frustrating information, because I knew there was no way I could compete with a man. Not becasuse he was better; because we were just different. We had different body parts, different personalities. I couldn’t compete with an MBA student with a dick, pure and simple. It was like we were on different planes.

If I had had any self-respect, I would have told Anna that I had feelings invested and needed to know her answer before it went any further and I got hurt. But I just wanted to keep making out with her. That lasted for a little while. But we would get home to her apartment sometimes to find roses from Jon, and it was just getting too painful. I told her I wanted to be with her. She said she needed to end it with me and Jon because she still couldn’t figure anything out. I was bummed. 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. We were both in a great mood. She invited me home and I was so excited. Maybe we would finally get to do things now that Jon was out of the picture.

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 didn’t want you walking home 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?” “No, she said, hugging me, “sleep in bed with me.” My head was about to explode from all the mixed signals. In bed I tried kissing her again, and she kissed me back. Then she pulled herself away and said, “I can’t! I need to take time.” She grabbed her retainers off of the night stand and 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 hten put your retainers in to keep ME away from YOU?” “Yes,” she said with a lisp. “I can’t believe this.” No one had ever tried to repulse me with orthodontia before, and it was pretty 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.

Note: This piece was originally published in Rebellious magazine and was republished with permission. You can find the original here.

Caitlin Bergh is a Chicago comic. She is the producer & host of The Funny Story Show at LooseLeaf Lounge and co-producer & co-host of Performance Anxiety Chicago at The Pleasure Chest and #LadyBros Comedy at Cole’s Bar. She is a winner of the Moth StorySLAM & has performed at Mayne Stage, The Comedy Bar, Zanies, Berlin Nightclub, Chicago Underground Comedy, as well as in NYC and LA.  You can also see her perform Tuesday, September 18th, at Town Hall Pub for Word Is Out: Outrageous.  The show starts at 8 o’clock, is 5 dollars at the door.

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