I Regret Everything: Not Being In A Relationship

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] thegloss.com or Ashley [at] thegloss.com

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.

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    • Hmmm

      god this is me at 20… now i’m nervous

    • Human

      This is me at 24. So don’t feel so bad. I’ve got it worse.

    • Teri Jensen

      If it helps at all, I spent the last thirteen years raising a child by myself and my focus wasn’t on relationship. My emotional development has been slightly retarded as a result and I am stiil scared of mern so there is that.

    • Teri Jensen

      If it helps at all, I spent the last thirteen years raising a child by myself and my focus wasn’t on relationships. I didn’t really start dating again until recently and my emotional development has been slightly retarded as a result. This coupled with less than desirable outcomes in the recent past has lead me to act little timid around men I am interested in. In other words, I am still kinda’ scared of boys.

    • Stephanie

      this is me at 23. nice to know i’m not the only one.

    • Caridad

      Why are so many comments from readers in their early 20s saying, “I feel behind already, and now I’m scared”?? I don’t see this as a “poor me” piece. Sure, there are things to regret (and I relate to that) but the path you take is your path, and you’re on it for a reason. I used to tell myself that I didn’t date because of religion. But now I see that I didn’t date back then because I just couldn’t go there. If it hadn’t been religion, it would have been feminism, or too-busy-working, etc. I wasn’t ready to be vulnerable, and if I had tried to date when I wasn’t ready, it would have been embarrassing and emotionally damaging. I think this author was really wise to avoid dating while she was raising a child. But it seems like that’s a really different situation than not being committed when you’re in your early 20s. Don’t beat yourself up. Open your heart when you’re ready. And when you find someone who’s ready for you, don’t be afraid of it — embrace it.

    • I am Thomas….

      Teri… come now…amazing girl… you need to be held for a while… just know there are those of us who adore you… would welcome your magic… so reflect upon it the right way…

      Christmas is here love….. so give of your heart… I adore you… I think you’re amazing…


      • Teri Jensen


        I adore you and how did you find this? You are an amazing, amazing man.

        The other “T”

    • lizajack25

      Beautifully written post. Identify with much of what you say too.

    • jay22

      Omg I def feel the same but I regret all my partners && its starting to really affect me so I just try to keep busy that kinda helps but this lonely feeling is always here

    • Veronica Haunani Fitzhugh
    • Jacinda

      This is me exactly at 21. Sigh, I’m afraid for my future.

    • smaktakula

      Let’s hear it for honesty!

    • Baghead Kelly

      You’ve confused an interconnect between sex & love. I don’t think there is one.

    • Let Life In Practices

      I just found your blog and read this post. I know many many people can relate to you. I just posted an article yesterday on relationships that I think you might enjoy. It is called The difference between falling in love and real love. I look forward to reading more of your writing.

    • sparkylaurie

      Terri, You are a strong woman… I love the fact that you are “picky” and refuse to consider guys who are not emotionally available. Thats totally wise thinking. You are a gem and make sure you take time and listen to your heart as you find the guy who sees that and more in you! You totally deserve life’s very best!Luv alwayys,

    • Asuna_Warrior

      i’m struggling with this at 26 (27 in a month). lately i’ve wondered if i need to really get out there even more and try dating again