This week at TheGloss, we’re featuring essays about regrets. If you’d like to contribute, feel free to reach out to Ashley or I at Jennifer [at] or Ashley [at]

I don’t have many regrets. I believe we learn from all of our experiences, good or bad. There are lessons in our experiences intended to help us grow. But if I am being entirely honest, I do have one. It is a huge one. I have never really been in a relationship. I am in my thirties and I have never dated a man for more than a few months.

I do want a relationship. I am actually consumed with my desire to be in one. I have become overwhelmingly envious of people in relationships. I see happy couples and I want to knock their heads together. I refuse to go to weddings because I am afraid I might punch the bride in the face.

I have always been deeply driven. I am driven in everything I do and most of my focus, over the past decade, has been on my work. Over the past two years that has changed. My priorities have shifted. I realized that I actually wanted a life beyond my work and that I didn’t want to live it alone. I really want someone to share it with.

I want a partner. It seemed simple enough. I could just be in a relationship, right? I am attractive and likeable. I would just find a man I enjoyed spending time with and I would have my relationship. It would be easy, nothing to it!

Turns out… I’m picky and I have a hard time opening up in intimate situations. Being choosy isn’t really my problem. I have a pretty good idea of what I want. When I meet someone I am interested in I know it almost immediately. This has caused me to act a little prematurely and that is where my first problem really lies. I haven’t had a lot of sexual partners but the underlying problem with all of my attempts at relationships is, nine times out of ten, I sleep with my perspective partners way to soon. I love sex so when I find someone I am attracted to (which isn’t often) I am eager to start creating premature emotional and hormonal bonds with the object of my affection.

Once these bonds are formed, once I start feeling something for a man, I tend to shut down. I don’t really discuss how I am feeling or what I truly hope to accomplish. This usually leads men to believe that I am just looking for a good time and that I am more than content to continue fuck-buddying it up with no expectations beyond our climaxes. I have hard time telling men what I want. By the time I get up the courage to tell the guy I am dating how I feel, I have already typecast myself as a “friend with benefits.” Things tend to fall apart from there.

I’m learning from my pseudo relationships and trying to apply those lessons in new experiences. I try to wait longer to have sex. I try not to date men I know aren’t emotionally available. I am working harder to let men know what I want. I really want to be in a relationship. I like the excitement of meeting someone new and establishing a connection I want all the normalcy of having someone consistent in my life. I want the security. I want the comfort.

I regret not being courageous enough to be honest and stop doing the things I know won’t work if I want a relationship. I regret feeling like something is missing in my life. My one all-consuming regret has turned into hundreds of little regrets. I regret that too.