Dating Sucks & I’m Working On Making It Fun Again

For a while, I was bitter as hell about dating and I certainly wasn’t having fun. Then with the help of a friend, I realized that I should really make enjoyment more of a goal. I’m not perfect, but I’ve made some big changes to truly have more fun when I’m seeing someone (or multiple someones) in the early stages.

  1. I was taking things too seriouslyI was very much focused on the fact that I was seeking a serious relationship. I had my blinders on and I was pushing anyone who wasn’t dead set on the same thing away without giving them a chance. Don’t get me wrong, it’s good to be on the same page, but I was so serious I was scaring people. I was also very serious in my judgment of others. I took it a bit too far.
  2. I’m keeping my standards but loosening them a bit. Don’t get me wrong, I’m not saying I should throw out all rationality and thinking, I’m just saying that I should ease up on it a bit because it’s ruining things. Nonetheless, I should still take figuring out compatibility seriously as well as feeling out safety or spotting red flags. Dating another human is pretty serious business because a lot is on the line. I have to have that balance though.
  3. A friend reminded me that I should be having fun. You know it’s bad when a friend has to stage an intervention. She was adamant that I should be having fun and she was tired of seeing me so miserable. Now I’m trying to look to my friends who are enjoying themselves more than I am and I’m trying to draw inspiration from them. It’s a good thing I had this friend to keep me in check.
  4. I think I was jaded about loveA big reason I wasn’t having fun was that I was feeling so dang beaten down by dating and love. I had my heart broken and I had crappy luck with online dating. As a result, it turned into a chore rather than something to be enjoyed. Now I’m trying to make it fun again and I’m making a concerted effort to be more optimistic. It turns out that what I put out into the universe is often what I get back.
  5. If I’m not having fun, I change course. If I realize that I’m not enjoying myself, I try to turn my mind back to pleasure. I also sometimes take actions like suggest we go for a walk instead of sitting still on a date or I end the date altogether if I’m just not enjoying myself. I’ve realized that I have the capacity to shift my focus, turning to a more positive outlook. This doesn’t always work, but often I can make it happen.
  6. I have to keep reminding myself. Meditation helps me a lot with this. Since fun is my object of focus, whenever I notice that I’m drifting away, I bring my attention back to my focus. It takes constant reminders to get it through my head that I’m in it for the fun. I have to remind myself when I’m talking to people and when I’m out on a date.
  7. I started having more creative ideas for dates. If I go to an arcade bar on a first date, who cares if the company’s bad? I get to play multiple games of Pac-Man and Skee-Ball. If I make sure that the date is creative and I’ll have fun no matter what then I can’t lose, even if the person themselves is actually disappointing. I’ve found this a fail-proof strategy and my dates often really enjoy my location choices.
  8. Overthinking and projection ruin things. Man, I love to overthink and project into the future, and these two things really make focusing on fun quite difficult. When I’m obsessing about all of the things that I should and shouldn’t know, like if someone is “The One” or not on the first date; when I’m projecting I’m creating a future for us in my head when we haven’t even finished our dinner—they’re both mad. I do my best to bypass and suppress them.
  9. If I’m not having fun, what’s the point? Why date if it’s not going to be fun? It’s not meant to be a part-time job, it’s meant to be magical, enjoyable, and silly at times. Sure, it can be dull and often unfortunate, but that doesn’t mean I can’t enjoy myself along the way. Shifting my focus like this has really made all the difference in my level of happiness.
  10. Now no date is a loss. I chalk every date up to an experience. I get to meet a new person and have a good time, so I leave winning. I also get to realize that they aren’t for me if that’s the case. I get to listen to my gut and act accordingly. Gotta love that.
Ginelle has been writing professionally for more than six years and has a bachelor’s degree in digital marketing & design. Her writing has appeared on Birdie, Thought Catalog, Tiny Buddha and more. You can follow her on Instagram @ginelletesta, via her Facebook page, or through her website at