Guys Say They Like It When A Girl Makes The First Move, But Whenever I Do It, It Always Gets Weird

Guys tell me all the time how they wished girls would approach them, but in my experience, every time I “woman up” and ask a guy out, it ends up being the most awkward situation of my life.

  1. It doesn’t come naturally for me. I don’t think approaching men comes naturally for ANY woman and it’s mostly because it’s just not the way we’re made. I think there’s a reason the guy traditionally asks the girl out. It’s the way it’s supposed to be and anytime I try to break the rules of nature, it always ends up going weird.
  2. It’s wired into a man’s biology to approach. The same way women can feel weird about approaching, guys are kinda wired to chase, so when I try to take on the role of pursuer, it always ends up making things awkward. I just need to accept that my brain is wired differently and there’s no reason I should force myself to do something that doesn’t feel good or natural.
  3. It puts unnecessary pressure on guys to pursue. The real reason my attempts at approaching guys always ends up in awkwardness is because of all the pressure it puts on the guy to make the next move. Maybe he wasn’t ready yet but was going to eventually do it but I still had to go ahead and force him into an interaction, making the whole thing a lot more stressful than it needs to be.
  4. It’s like I’m interrupting the natural flow of things. Whenever I ask a guy out or tell him that I like him, it feels like I’m interrupting some kind of intricate process. The type of guys who pursue me seem to take FOREVER just to make a move, so I figure that if I just do it, it’ll all move along faster and we can start dating sooner rather than later. The thing is, though, it rarely ever ends that way. It’s almost like my action puts a fork in the road of the attraction that was already growing between us.
  5. I’m already an awkward person to begin with. I’m the last person who should be taking it upon themselves to approach guys. I feel like it takes a certain personality and boldness to take that kinda risk, go against societal norms, and ask a guy out—and I just don’t have it. I’ve seen my friends do it with style and grace, but when I do it, it’s like a cringe fest. I just can’t pull it off.
  6. The guy is weirded out that it’s even happening. Even the act of a girl asking a guy out (awkward or not) is in itself kinda weird because it pretty much never happens! Guys aren’t used to it, so they kinda freak out in the moment and don’t know what to do. I would love for it to eventually be normal but I think we’re a really long way from guys not instantly falling into insecurity and awkwardness when they get asked out by a girl.
  7. It probably knocks me down a couple of pegs in their book. Everyone wants what they can’t have and when I’m basically throwing myself at them, it probably makes me that much less attractive in their eyes. I’m giving all the power to them from the get-go and if I was already nervous before I approached, now I should be REALLY nervous.
  8. I don’t know how guys do it. The way guys put themselves up for potential rejection time after time is nuts but I guess it must be worth it to them because they never seem to give up. Maybe they see women as more valuable than we see men. Either way, I’m not willing to put my dignity at risk just for a shot at dating a guy I think is cute. It doesn’t seem like a fair trade-off for some reason. Maybe I should follow that instinct and sit back.
  9. Desperation is one of the most unattractive qualities in the history of the world. I can’t really keep my cool when I approach a guy, especially since I don’t really do it that often. There’s a really good chance that I’m coming off as desperate, which is SO not sexy.
  10. It seems to make the guy more nervous than anything. My intention is to captivate the guy with my charm and wit but it usually ends up just making him nervous and awkward. Not my intention AT ALL, so I think I’m better off waiting for him to approach me.
  11. It’s almost like I don’t trust them to make a move on me. The thing that probably shakes them up about being approached is that they probably think that I don’t think they had the balls to do it, so I had to just do it myself. Even though that’s not AT ALL where I’m coming from, I can tell they’re thinking it.
Jennifer is a playwright, dancer, and theatre nerd living in the big city of Toronto, Canada. She studied Creative Writing at Concordia University and works as a lifestyle writer who focuses on Health, B2B, Tech, Psychology, Science, Food Trends and Millennial Life. She's also a coreographer, playwright, and lyricist, with choreography credits for McMaster University’s “Spring Awakening,” “Roxanne” for the Guelph Contemporary Dance Festival, and “The Beaver Den” for The LOT, among others.

You can see more of her work on her Contently page and follow her on Instagram @jenniferenchin.
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