How Being Single Shaped Who I Was In My Twenties


When I was in the 7th grade, I confessed my feelings to my one and only ~tru luv~. I had been in “childhood love” with this boy since basically kindergarten, and we were friends, so I wasn’t sure how he was going to take it. We were lined up at the classroom door, waiting for the bell to ring to signal our freedom for the afternoon, when I turned to him and said, “Hey, there’s something I’ve been meaning to tell you for awhile. I like you. Like, I really like you.” He looked at me with a confused grin on his face, and then the bell rang and off we went to our separate buses home.

He smiled, I thought. That was definitely a smile. Okay, cool. I did it. I was feeling pretty badass. I had finally spoken my truth, and now all I had to do was wait for the next school day. So, like most children growing up in the very early 2000s, I went home and immediately logged into AIM and impatiently waited for the opening door sound effect to tell me that he had logged on. I don’t remember if he ever logged on but I do remember telling all of my friends what I’d done and all of them being completely in awe of my “balls.”

Naturally, the next school day comes and I feel like I’m going to vomit having realized the vulnerability I’ve opened myself up to. I also feel like I’m going to vomit because today is the day we are dissecting frogs, and just, gross. When I get to school and locate THE ONE, I find that he is practicing complete avoidance of me on every level. I’m not kidding, I’ve never seen anyone go about a task with as much concentration as this boy dissecting his frog. Eventually the awkwardness died down, but he never acknowledged what I’d said to him. Though one day in the 8th grade he did let me wear his watch, which was basically as dramatic as being given an engagement ring in my 2004 world.

I am now a 26 year-old grown ass woman, but I remember this story so clearly because much of my romantic life as an adult has played out in a similar fashion (minus the whole watch-wearing phenomenon). I’m a very honest person by nature, and I love confrontation because I find it so much more relaxing to have answers than to have awkwardness. A lot of my romantic history involves me developing feelings for a friend, telling them, and then seeing how it all plays out.

I met with my new therapist in Chicago last week and she was asking all the basic questions, one of them being about my romantic history. I genuinely did not know how to explain to her that I’ve sort-of had relationships, if you can call them that. But I’ve never been in love, I’ve never been referred to as someone’s girlfriend, I’ve never met a guy’s parents. But I have fallen hard for people and I’ve had my heart broken. I have been in a lot of intense situations that all played out the exact same way: girl and boy go to school together/work together/have all the same friends and see each other every day, one or both of them expresses feelings, one or both of them does something stupid, everything goes up in flames. The life-span of these relationships is about 3 weeks max. And repeat.

Up until my move to Chicago, I had never gone on a date with someone I was not already very close friends with. I couldn’t do the online dating scene in LA because I was too nervous and I didn’t really want to date anyway. Besides, who has time for online dating when you’re in the middle of a dramatic love triangle at work that every single one of your coworkers knows about? Good times, good times.

I used to have a lot of shame about the fact that I’m in my mid-twenties and not only single but a total relationship noob. Growing up, I had no examples of how to be a single woman. I was consistently the only friend without a date to the dance or a boyfriend and all of the women in my family were married straight out of college. This caused a huge issue for me mentally, and it took me years of therapy in college and in my first year post-graduation to work through it all. My eating disorder was born out of a desire to become thin enough where men would be interested in me. I was convinced that any man who did show a spark of interest was the last man on earth who would ever do so, and then when he left, I was incredibly broken. I wanted a relationship so badly that I forced the issue with everyone, but I never actually believed I was worthy of being loved, so I consistently chose men I knew were incapable of sticking around or staying loyal or being a good person. For months after a particularly bad “break-up” I refused to do anything social, anything where I would be around men at all, because all they did was hurt me and I was tired of it. Like I said, I used to have a lot of issues with being single. Therapy is a godsend, friends.

Fast-forward to modern day, where I am still very much single, but I’m also pretty dang happy. I have A LOT of friends who are in committed relationships, some of them married. I also have plenty of single friends, and now that we’re all getting older, it’s so interesting to see how everyone is approaching their dating lives. We all have the friend whose wild and crazy days are far from behind him/her, and we all have the friend who can’t seem to stay single for longer than a month. Some of us aren’t even trying to find a boyfriend or girlfriend, some us of want one so badly that just about anyone will do for now.

Dating for me right now is a comedic adventure if nothing else. I honest to God do not have the time to be dating multiple men while I’m working 5 jobs and trying to create a new career. But I’ve also never been more motivated to put myself out there and see what happens. I recently joined the millions in the online dating sphere and because I go balls to the wall on everything in my life, I, at one point, had them all up and running: Tinder, Bumble, Hinge, The League, OkCupid (serious side note: are there more creepy guys anywhere on the internet than on OkCupid because DANG), Coffee Meets Bagel. I even filled out a profile on Match before I realized that shit costs money and I’m not at that phase of life right now.

Since January, I have gone out on dates with 13 different men, mostly from Tinder and Bumble. I have 36 phone numbers in my phone right now with contacts whose last name is Tinder and I honestly don’t remember who any of them are. I’ve made plans with and bailed last minute on at least 10 guys. I’ve met exactly two men that I genuinely, truly had a connection with and liked a lot. One of them took me on an incredible second date filled with surprises that ended with great seats to a White Sox/Indians game. He has since fallen off the face of the planet, never to return a text again. The other one I met for a drink at a bar and I felt like I was in an episode of Gilmore Girls because our witty repartee was something to behold. He said he’d love to see me again soon for a second date. He has officially ghosted me after I asked him to hang out again a full week after our first date. Honestly, it’s really hard to keep putting yourself out there when the results are so disappointing. I know so many people who met their current and serious partner through Tinder or Bumble, and it’s hard to know whether it’s time to take a break or whether to push through and hope I meet a great guy soon.

I was thinking about that dilemma last week when a friend of mind (HAYYYYY MARIA!) reminded me that online dating isn’t the only way to meet men, it’s just the only way I have met any men in Chicago so far. And then my therapist pointed out that it doesn’t seem like I’m having any fun dating. So the question remains, do I keep going? Do I stop? Why do I care so much about finding a boyfriend now when I’ve got so many other things going on that I could devote my energy to? Is it because I’m getting older, and this is what society tells me I should be doing? Is it because I’m afraid I’ll end up alone if I don’t hurry up and find a good man? What happens if I just chill out and get comfy with my new life first? What will people think of me if I’m content being alone right now? I really don’t know the answers to any of these questions, by the way.

I know he isn’t everyone’s cup of tea, but I think John Mayer is a lyrical genius. One of my favorite songs of his is called “Age of Worry,” and in the song, John sings: “Don’t be scared to walk alone. Don’t be scared to like it…Go out in the age of worry and say “Worry? Why should I care?’” I’ve always been an independent soul, sometimes to a fault, but it’s the thing I like most about myself. I’ve never been the type of girl who felt like she needed a guy around to kill bugs in the apartment, fix a slow drain or be a shoulder to cry on. I buy my own flowers, change my own smoke alarm batteries and see a lot of movies by myself.

I am so, so happy that I have been a single gal in the world during my twenties. I have been able to explore my early twenties without ever once feeling like I owed anything to anybody else. I’ve uprooted my life and moved across the country twice without hesitation. I never have to “check-in” with a boyfriend before I commit to something I want to do because I’m not sure if he’s already made plans for us (what’s with that anyway, ladies?). I’ve lived a full life based on choices that I alone have made. I know exactly who I am and what I want out of life and none of that is tied to another person’s plans or expectations.

Do I want to be in a relationship? Heck yeah! I like doing nice things for guys I like, and it would be nice to be treated well and taken care of myself. I’d like to have the support of someone in my corner who tells me I’m pretty and laughs at my jokes and buys me flowers so I don’t have to buy them myself. I would love to have someone to text during the day when I find amazing videos of puppies being stupid and always have a plus-one at the ready for wedding and party invites. But I’m not mad at the fact that I’ll wake up tomorrow knowing that I’m a complete story all on my own, and that is a beautiful thing.