I’m Way Too Cautious In Dating & It’s Kept Me Single For The Past 3 Years

When people ask me why I’m single, I’ll say cliche things like that I haven’t found the right person yet, I’m really picky, or even that I don’t feel like dating right now. The truth i that deep down, I know it’s because I’m way too cautious in my approach to finding love.

  1. For starters, I’m already scared of men. Forget my innate tendency to be cautious when it comes to dating—it’s hard to really dive in head-first when I’m so terrified of guys. I’ve been this way for as long as I can remember and I don’t know why. Still, maybe that’s the reason why I go for meek, slightly feminine guys. The risk of getting hurt by one of those big, manly men is just too scary.
  2. I have an insatiable need to protect myself. The second I enter a relationship, I put the walls up. I grew up in an unstable family environment so I’m always on the lookout for signs that my relationship is on shaky ground. I’m not one of those people who can just throw caution to the wind and dive feet first into a new relationship because for all I know, it’s going to hurt me in some way.
  3. Nothing is scarier to me than being stuck in a relationship with someone I hate. I’d rather be alone forever than be stuck with the wrong person. I’m not someone who gets along easily with people so the idea of being trapped with someone for all of eternity is like almost as bad as hell itself. This is why I tend to keep one foot in and one foot out of my relationships. What if he’s not “The One” and I make a major mistake?
  4. I take pickiness to a ridiculous level. I often disguise my cautiousness with pickiness in dating. I’ll manage to find a ton of teeny flaws in a basically perfect guy. He could be a goddamn saint and I’ll manage to make him seem like a total a-hole. It’s my way of making sure I’m with the right person. If I’m not scanning him for flaws then I might find myself totally unhappy and not knowing how to get out years down the line.
  5. Maybe I’m just afraid of rejection. I’m well aware that these cautious habits of mine are fully based in fear. I’m afraid that it’s not going to work out and I’ll be rejected or betrayed in some way, so instead of taking my chances and going for what I want like most people do, I stay scared, curled up in my safe little corner, never taking a real chance on love.
  6. I feel like I’m missing out. I can’t even count the amount of times that an opportunity for a new relationship was presented to me and I totally and completely messed it up with my insecurity and cautiousness. All of my friends have had these amazing love stories but the farthest I’ve ever gone with a guy is leaving my toothbrush at his house.
  7. I always imagine the worst case scenario. For some reason, my mind always assumes the worst and I feel like I can’t control it. The second I get a prospect for a date, my mind starts scanning the situation and goes over literally every single thing that can go wrong. It’s exhausting. Why do I do it?
  8. Sometimes I literally run away from guys who talk to me. I don’t even think I could consider this “cautious” behavior because it’s just so extra. Sometimes when a guy comes up to me, I get so scared that I literally run away. Sometimes I give an excuse, but more often than not I just pretend I didn’t see or hear him and run away. It’s a serious problem.
  9. I assume that guys aren’t serious about me. A big reason I’m so cautious with dating is that I don’t trust that guys who say they’re interested in me are being genuine. I don’t really have any proof that they’re not, I just believe deep down that I’m not a very good person to date. Maybe I need some therapy…
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.