To the mediocre bartender,

I had to teach you how to properly make a mojito and I’ve never even been a bartender. You looked cute in your bartending suspenders, which caught my eye, but we had absolutely nothing in common. I knew things were going south when our fourth date was a trip to your gym and I had to pay for my own guest pass. Why do you talk about drugs so often if you allegedly don’t do them? You also claimed that you used to run 7 miles in 30 minutes on a regular basis, which I found extremely hard to believe. After saying you were a “relationship guy,” but quickly declining when I asked if we were going to be in a relationship after five weeks of getting to know each other, things ultimately ended in tears for me while you quickly left my apartment on my birthday while my cat stared you down. We never spoke again and I think you’re okay with that.

To “Florida Boy,”

We bonded over our mutual fear of dating bartenders due to bad past experiences (see above). I thought you were a safe bet, since we went to the same high school, although we ran in different circles for clear reasons. The cockiness you displayed in high school that you claimed was now confidence is definitely still cockiness. You just have more money now (so you say). You thought it was somewhat comical that you were mean to your coworker for being new and asking a question, which is no surprise, since you got into numerous fights in your teenage years and early twenties. You almost got evicted due to righteous indignation, and almost got charged with a hit-and-run, all within the same few weeks I was getting to know you. Although I technically ended things between us because you said something grossly disrespectful, your lack of apology and ease of letting the situation go made me feel like I was the one being rejected. That’s the only reason you’re included in these letters. I hope your new girlfriend never finds your secret Twitter account and sees all of your disgusting misogynistic tweets. On second thought, I’m sure new women you date won’t find it, because you probably won’t want to date another intelligent woman who can find your secret accounts like I did. Smart women are too much of a challenge to your ego. In your own words, I wish you the best. I hope you find what you’re looking for. Take care.

P.S. – Just reach out to your bartender ex-girlfriend already. You clearly still love her.

To the best kisser I’ve ever met,

I feel like I can safely be honest in this because I know you’ll never read this, since in hindsight, I don’t think you put as much stock in our conversations as I did. You probably don’t even remember that I write, and you definitely don’t know which magazines I write for. I’d be surprised if I ever even crossed your mind at all. However, these are all negative assumptions I’m making, which is something I am aiming to work on. Months ago, I saw an episode of Dr. Phil that really resonated with me where he said, “Not everyone you lose is a loss.” The first time I wrote this letter, I was still very much longing for things to be different and for you to realize my value. After countless therapy sessions (you said I was the one who needed therapy, right?), prayers, crying spells, and efforts to somehow learn to love myself, I asked our editor to let me revise it after concluding that even though you were the one seemingly uninterested in pursuing something real with me, you were truly the one who lost me. Whether it was your age, potential substance abuse issues, different wants and desires, or a combination of the three, you mishandled me. At the same time, I should have known better than to get attached to an idea of something that was destined to fail. A part of me does wonder and I frequently ask God why I am continuing to go through so much pain after so much time has passed from such a short-lived fling (well, a fling for YOU). An even smaller part of me still hopes that things will somehow work out in the future after we both sort out our issues, but I know life rarely works that way. Hoping is only holding me back from healing. My friends and family keep assuring me that with the right person, I will feel passion and butterflies again the way I felt them with you when we kissed on the beach. Most days, I don’t think that’s possible, but my therapist told me to keep assuring myself that I will find it again until I believe it.