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Dating in Your Twenties

  • The Twenty Something
  • Aug 12, 2023
  • 4 min read

Is it just me or does dating in your twenties feel impossible? I spend hours swiping on dating apps and it usually ends one of two ways. I immediately swipe left or the guys I swipe right on don't swipe right on me. It's a torturous cycle. And every dating app is the same.


In a city of 8.4 million people, why is it so hard to find "the one"?


Finance bro after finance bro and they're all variations of the same. Do I have to sacrifice what I want to expand my dating pool?


I went on a date recently. I had matched with this guy on a dating app and he seemed nice. On paper, he was exactly what I want. He didn't message me for a few days and I thought - oh well moving on to the next. When he did finally message me, our conversations were nothing exciting. He would ask me how my day was and I would do the same. With both of our busy schedules, it was nearly impossible to find a time to actually meet in person. We tried making plans for almost a month. Texting about our days became so routine, so mechanic that I hadn't realized how much time had passed.


This guy would consistently only ask me out at 8:00 or 9:00 for plans that night. And the plan was always to go to his apartment and hang out. I'm an elementary school teacher, and 9:00 is past my bedtime. I have graduate school at night and spend my time after that doing homework, so last-minute dates don't work for me. Not to mention they show no thought went into planning the date. If we can even call hanging out a date. But the bigger red flag was that he thought I was going to hang out with him at his apartment at night when we had never met before. How do I know he's not a serial killer? I don't! Because we've never met. And we all know what going to a boys' apartment means...


When I mentioned something along those lines to him, he suggested we facetime. We did and it was weird, but not as terrible as I thought it would be. I was left unimpressed and he definitely wasn't trying to impress me. I had suggested going out for drinks and doing something fun, but he always shot me down.


When we finally found a time I sucked up my gut feeling and went to have wine with him on his rooftop on a Tuesday night. I knew I had to be up early for work the next day, but I also knew I'd regret it if I never gave him chance.


He texted me earlier that day saying how excited he was and that made me feel more excited because it showed he cared. On my way there he asked me if I had eaten dinner. When I said no he was relieved and asked if I minded if he didn't get snacks. Of course, I said no, but I did mind. On principle, he could bring snacks to a wine and snacks date. Red flag. I fought through the icky feeling and actually had a good time on our date. He was nice and easy to talk to. We had a lot in common and knew some of the same people.


Towards the end of the date he made his way over to my lawn chair and I knew that meant he would try to kiss me. When he did, I politely declined and he took it well. I thought wow points to him.


He texted me immediately after the date. The next day he asked me out again. As usual, it was for later that night, He said he was going out for dinner with his sister and could hang out after. I, unfortunately, could not, nor did I want to so soon after the first date. I did not feel the sparks. In fact, I felt nothing which has been the trend after most of my dates.


We continued to text for the next few weeks. He still asked me to hang out, but again we couldn't find the time. I eventually became annoyed with his lack of planning and desire to only hang out with me late at night at his apartment. I don't know what type of girl he thinks I am, but that was NOT happening.


When he could feel me pulling away he asked me straight up if I wanted to see him again. I spent a lot of time thinking about it. Should I go on a second date just to see if my feelings change? But I was also annoyed that once again he was only asking to hang out at his apartment for that night. I decided to send him a text and however he responded would give me my answer for how to move forward. I told him it was difficult for me to make plans so last minute because of my busy schedule and that it would be better for me to know in advance so I can adjust when I'm doing things. It was very to the point. He liked my message and that was it. That was how I got my answer. If he wasn't going to man up and actually plan a proper date in advance like a gentleman then he wasn't worth my time.


It was in these moments that I had to remind myself who I am and why I believe so strongly in romance. I deserve to be treated like I'm special. I deserve to have someone who shows me they care by putting effort into planning a date. I deserve more than what this boy was giving me. I had moments of self-doubt. Moments when I thought maybe I'm asking for too much. But that's not true. The dating culture today makes women believe that asking for the bare minimum is asking for the world. I'd rather be alone than be with someone who doesn't put in any effort. If they don't put in the effort at the beginning when everything is supposed to be rainbows and butterflies, then they never will.





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