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Why I’ve Given Up on Dating

I remember my first real date. Mostly because it was a disaster. I was in school on Long Island and this guy I met online asked me to come to his apartment for dinner so I put on a cute outfit (or whatever I considered cute back then) and took the train into Brooklyn. I remember getting off the train and thinking, with certainty, that I was in the middle of nowhere… (For Brooklynites: I got off at the 7th Avenue B/Q stop, so far from the middle of nowhere). I got to his apartment and he was cooking dinner, which for someone as picky as I am is always a nerve-racking event.

He made a salad that was roughly 60% black olives (I hate black olives) and a mushroom risotto (I hate mushrooms) and spent the entire meal telling me about his elaborate idea for a musical (it involved time travel) while we ate on his couch. At one point he leaned down to kiss me while I was in the middle of telling him I should go and when I moved away he began to yell at me about not telling him I wasn’t interested right away.

“Hi, wow dinner looks great! By the way, I’m not really feeling this, but let’s eat!”

I grabbed my coat and headed back to school knowing it could only go up from here… Eight or so years later and I am not sure it did.

Sundae Co. | Ross & BF1

I’ve done my fair share of dating, some not even worth mentioning to my friends and I’ve dated some really great guys who for one reason, or a million, it didn’t work out. In an extremely abbreviated version, here is my dating history, as I choose to remember it:

At 20, I told a boy “I love you” for the first time. I had never met this boy in person. We met on Tumblr and he lived in California. We spoke daily and when we finally met after months of speaking, it fell apart quickly afterwards.

At 23, I dated a 36 year old who cheated on me with his ex the entire 2 months we were together. He broke up with me over dinner after I told him I don’t think we should be together anymore.

At 24, I met at a guy at a holiday party thrown by some college friends of mine and we dated for over a year. I broke up with him because we weren’t compatible in any way other than as friends, but both failed to see it for 13 months.

At 25, I met a guy on Tinder. He was insanely attractive, talented, outgoing and selfish. I broke up with him after a few months because I felt more like an object to show off then a partner in a relationship. He still hasn’t returned some of my stuff.

At 26, I wanted to keep things casual with a 32 year old who wanted to be monogamous. We never really settled on what we “were” and ended up both sleeping with other people and broke up shortly after.

At 27, I met a guy on a “dating” app while he was in town from another city. We talked almost daily and I visited him for a long weekend a few months later. He moved to NYC, we went on a great vacation together and I was really happy. He broke up with me because he was too busy for a new relationship.

Sundae Co. | Ross & BF2

So, here I am. 28 years old and after some self-reflection (and a little therapy) I have decided that dating is just not for me. I’m at the point now where I think I can accomplish all I want to accomplish much easier if I am on my own. I love to travel, but on my own itinerary. I love spending time with friends without worrying about anyone else. I love to watch what I want to watch and eat what I want to eat and clean when I want to clean. This is why I live alone. This is why my family calls me selfish. I may seem selfish, but I like to think of it as self-sufficient and independent and strong-willed?

Sundae Co. | Ross & BF3

As I become more comfortable with this decision, I become more hopeful about the future. I no longer put pressure on myself when meeting new people or going out with friends. I do not worry that I look good for strangers, I only want my friends to think I look good. When I mention this new outlook to friends, they all say the same thing: “So, if a really handsome guy walked up to you and asked you out, what would you say?”

“Oh, that is very sweet, but no thank you.”

They laugh it off and tell me I am crazy, but I have already turned down one or two handsome guys and didn’t bat an eye at it. It is genuinely not something I am interested in right now and I am not sure when (or if) I will change my mind about it anytime soon. And yes, I am still interested in having sex. And no, not just a bunch of random hookups. I am not sure what my sex life will look like now that I have sworn off dating, but I am working on that and truth be told, sex is something I care about less and less these days anyways. (Oh, my Mom reads this huh?)

Sundae Co. | Ross & BF4

Mostly, I just got tired to getting to that point in a relationship where I let myself open up to someone and start to let my emotions get involved only to wind up disappointed and heartbroken X amount of days, weeks or months later. I do not want to experience that again if I can help it – and I can, by not getting myself in that situation again.

With the time and energy I would have spent on dating, I am fully devoted to working on myself. I am going to get back to the gym. I am going to cook more. I am going to read more. I am going to write more. I want to travel and be around my friends. I basically want to date myself. I’ll buy myself nice gifts and take myself on dates to museums or the park. I need to court myself back into being the confident, sexy, outgoing man I know I can be. And if I tried so hard in the past for guys I was dating, why can’t I try that hard now for me?

So anyways, that’s my new outlook on life and love and how I maybe don’t believe it anymore? 2017 is turing out to be quite a year!

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  • Reply Fajj Greenberg February 2, 2017 at 2:18 pm

    Umm…your Father is reading this too… There’s nothing wrong with a little self-reflection & a little “me” time. You’re deciding several big life decisions now so this is a good thing. Love you.

  • Reply Productive Ways to Endure Valentine's Day as a Single Person | Sundae Co. February 9, 2017 at 8:03 am

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  • Reply Alex February 17, 2017 at 3:58 pm

    Ross, I hope this new relationship with yourself is the most rewarding and romantic of all! Chin up, heart open, my friend.

    • Reply Ross Greenberg February 17, 2017 at 5:04 pm

      Thanks Alex! I hope so too!

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