How Not Trusting My Gut Led Me To Heartbreak


When I moved to Chicago for grad school as a 24 year old socially awkward virgin, Tinder became my saving grace. Initially I had no intention on meeting people in real life. The thought of actual face to face conversation with a stranger gave me anxiety and I had an unfounded fear that I looked substantially better in photos. Eventually though, I became a regular with the Tinder dates. It became fun to meet new people and I became a savage for the free stuff, like meals and movie tickets. 

 When I matched with *David, 27 I was excited. He had enough of a Jewish name, big nose, and curly hair to satisfy my mom but a nose ring and a denim jacket that I imagined to smell like weed and cheap beer to make me happy. So when he invited me to a free sold out Death Grips show, I was in. The date went okay. A lot of first date awkward small talk. I found out he never graduated college, currently served at a pizza place, was a year ago wanting to marry his best friend who he wasn’t involved with romantically and start a life on his barista wage, and was debating a fake green card marriage for the money and free vacation. All these things took him off my long term list, but he was nice and I reluctantly agreed to hang out again. The next couple times we hung out I learned how uncertain of a person he was and how he was still trying to figure out his life. He then asked me out on a more formal dinner date and followed up with flowers. The date felt like our awkward first date, which I knew shouldn’t have been by date 4.

I was conflicted. I didn’t feel like something immensely special was there but he was so into me and was sweet. I ultimately decided we were better off as friends and I tried to set up that dynamic. It went great for a while until, thanks to alcohol, my thirsty side reared its ugly head. We had a drunk make out and it changed everything. I still knew I wasn’t totally into him but thought we could be cuddle buddies on the low. 

Eventually though, he was spending every night at my place and took my virginity. I officially had a boyfriend and didn’t fully know how it happened. I rationalized this by acknowledging that I had the tendency to go after guys who aren’t interested, so why not give a nice guy a shot? Or, maybe I don’t like him that much because he made himself so available?

Months went by and I was still uncertain. At his sister’s bar, one pitcher of sangria in and inside the men’s handicap bathroom stall, I started bawling with him because I wasn’t obsessed with him the way I have been about other dudes. He ensured me how certain he was about me, about us, and about our future. I made the mistake of trusting him over my own gut. I thought, for someone who is so unsure about their entire life to be certain about me, this had to be some sign. 

After 6 months of steady dating, I was finally all in. Being in love was great! I could now tolerate awful Kate Hudson rom coms, couples holding hands didn’t make me nauseous anymore, and I started Facebook liking old friend’s engagement and baby announcements. I was as infatuated with him as he always was with me and I sort of appreciated the slow to warm process it took. We did great for a while. He visited my hometown, I went to his family reunion, and we spent every free moment together.

Shortly after, things changed. David was acting different and I didn’t know why. He was less affectionate and no longer the nice guy I thought I knew and fell in love with. I felt like something was wrong and suggested we take a break. He insisted that was not what he wanted. As things continue it became toxic. I found out he was social media creeping his old 19 year old fling regularly, so I called us over. He showed up an hour later with coffee and what I thought to be a sincere apology. Of course I took him back. 

A week went by and things still felt off. He eventually decided we should break up. This was unsettling to me because I was blinded by love and I remember how in love with me he was just week ago. Now, almost a month later, the whole situation still makes me cry. I saw him a week after the break up for a friendly drink. I knew it was still too fresh but I couldn’t resist. He was doing extremely well and didn’t appear the slightest bit sad, while I was fighting back tears. I was hoping hanging out would rekindle some old flame for him, but it didn’t. 

I’m trying to find peace in the fact I may never know what exactly went wrong. I’m working on moving on, but one thing I’ve learned is that when it comes to love, trust your gut.