I Asked A Guy Where Things Were Going & Never Heard From Him Again

Recently, I either went on a handful of dates or hung out with the same guy a bunch of times. I’m not actually sure if he considered them dates – he paid, but wouldn’t let me know how he was feeling. Finally, after several weeks, I sucked up my courage and asked where things were going… only to never get a response. Here’s what I learned from this all-too common experience:

  1. I don’t regret it. It was only when catching up with a friend over dinner that I realized sending a guy a text saying he was being confusing and asking if he was even interested in me was a big deal. I figured it was weirder not to say anything and I don’t regret it for a single second.
  2. Gen Y is immature sometimes. When someone is texting you constantly after dates (or “dates”) and yet refuses to make plans right away or be more obvious about his intentions, you can be sure that this person is pretty immature. Our generation seems to allow for this kind of immature behavior since apparently being part of Gen Y means hiding your feelings. I’m not into that.
  3. Other people mean well. This situation was new to me so I got tons of advice from friends and family friends. Everyone seemed to think this guy was into me and wondered if he was just shy or inexperienced. Eventually I realized that while other people mean well, you have to listen to yourself.
  4. I didn’t waste my time. It seemed super obvious that things would continue in this vague, super casual way if I never said anything, so it was good that more of my time didn’t get wasted. Not that it was a waste of time so far – any experience is a good one if you leave knowing more than when you went in – but spending more time would have been ridiculous.
  5. Red flags can be subtle. Sometimes things just don’t add up and that’s the biggest red flag of all. There was nothing “wrong” or creepy about this person. They were cute, nice, friendly, funny. But something didn’t seem to add up and then I realized that his cell number didn’t have an area code that would make sense for my city. Now I have no idea where he actually lives.
  6. I felt powerful. Sending that text was a risky move and the outcome didn’t even matter because it was enough that I was able to speak my mind.
  7. It felt natural to ask him. I’d rather date the old-school way, whatever that means. If that equals being honest about my feelings and wanting someone to do the same, so be it.
  8. Bravery is always a good thing. Our way of dating is definitely making us all a little less brave. We hide behind our phone and laptop screens and think that silence is an acceptable response to the hard questions in life and love. I’d rather be brave any day.
  9. I would do it again. It was scarier in my head and once I did it, I wasn’t afraid anymore. Refusing to tell someone where things are going is only going to ensure that you’re single forever and ever.
  10. It will happen again. Unfortunately. But that’s OK — now I’m ready.
Aya Tsintziras is a freelance lifestyle writer and editor from Toronto, Canada. In addition to writing about dating and relationships for Bolde, she also writes about movies, TV, and video games for ScreenRant and GameRant. She has a Political Science degree from the University of Toronto and a Masters of Journalism from Ryerson University. You can find her on Twitter @ayatsintziras and on Instagram @aya.tsintziras.