Playing It Cool Almost Ruined My Love Life

I thought that trying to be easy, breezy, and totally down for anything would make me irresistible. As it turns out, pretending to be ultra low maintenance led to constant disappointment. I didn’t feel like I mattered in relationships and guys just seemed annoyed with me. Lesson learned.

  1. I sucked at texting. When should I text back? Is this too flirty? Not enough? Instead of just being myself and messaging back whenever and whatever I felt like, I tried so hard to act casual that I’d get messages back asking if I was still there or why I always ended every sentence with “haha.” It wasn’t acting chill, it was acting fake and it didn’t do me any favors.
  2. Spoken conversations weren’t much better. I was so afraid of saying the wrong thing that I didn’t say anything at all sometimes. If I hadn’t heard something a guy said after I’d already asked him to repeat it twice, I’d just giggle instead of asking again. Giggled! Even when what he said probably wasn’t funny! Cue the awkward pauses.
  3. I let a lot of things slide. Missed plans, late night texts, taking a week to call me back with no contact in between—I let it all go. No one wants to be a nag, right? In my eternal quest to be perfectly chill, I ended up neglecting my own standards for a happy relationship. I felt undervalued and unimportant, but I didn’t say anything to fix the situation. Instead, I bottled it all up, and the next thing he knew, I was angry for seemingly no reason. It wasn’t healthy or fair for anyone in that relationship.
  4. Going with the flow rarely made things easier. When the answer to where you want to go for dinner, what movie you want to see, or what you want to do on Friday night is “I don’t care, babe, you pick,” the night usually ends in frustration. I learned that the hard way when one ex actually got angry about it the hundredth time I deferred to him on a decision. Not only is it easier to choose when you can collaboratively narrow options down, having an opinion really helps establish you as equals. You each feel like you’re dating a mature adult capable of making their own decisions, not a child that needs to be guided along in life or given permission.
  5. I ended up wasting a lot of time. I went on dates to movies and malls in which I had no interest because I didn’t want to seem picky and had conversations that felt too much like small talk because I couldn’t direct them more meaningfully. Relationships fizzled, and it was because I was putting my work into all the wrong places. Instead of trying to protect this Cool Girl image by keeping everything surface level, I should have been taking more risks in order to get to know people and build a more satisfying relationship.
  6. Saying no wasn’t easy. I’d gone along with everything he wanted to do until now, so why start pushing back? I felt guilty whenever I said no to guys who wanted to go farther physically than I did and I’d apologize for it a million times (even though I had every right to say no!) and make it all into a bigger deal than necessary. It would have been so much easier to be confident enough to talk it out and set some clearer boundaries.
  7. I didn’t share anything with my friends. I didn’t want to make a big fuss about a new guy in front of my friends, so he was always “just someone I’m kind of seeing, NBD.” Privately, I was of course already head over heels for him, but heaven forbid I show more emotion in public. Acting casual seemed better than gushing but in reality, it just sent the message that I didn’t care about him. In one instance, it spread into the relationship itself and made my then-boyfriend feel like I didn’t want him.
  8. I was always anxious. I didn’t look forward to dates because I knew I’d spend them overanalyzing my every word and movement to make sure they were perfectly cool. Dating just wasn’t fun anymore, and I never allowed myself to get comfortable and start learning and understanding guys on a deeper level. Eventually, I decided to stop dating altogether and hit reset.
  9. Trying to avoid causing problems just caused more of them. Speaking up is always better, even if it causes tension—and it was all about avoiding tension. Going with the flow made me boring and stressed out, but having opinions, making decisions, and being more upfront about what I want gave me an identity. If doing all of that creates problems, I’m OK with that now because I know that even a good relationship has its issues, and working together to solve those problems makes the relationship even better.
Samantha is a freelance writer living, reading, swing dancing, and cooking in Boston.