Confession: I Try To Date Losers So That I’m The Cool One In The Couple

I know this sounds a little counterproductive and also a little rude, but I actively seek out losers to date so I seem like the cool, attractive one in the couple. It sounds like a nutty thing to do, but trust me, it’s worth it.

  1. My self-esteem is already so low. I can’t even imagine how I would act if I was dating someone cooler and more attractive than me. I would probably get super jealous and paranoid. Maybe that’s why I stick to the losers? If I date a loser, I know that I’ll always be seen as the “better” one and that’s comforting to me. My low self-esteem can’t handle anything else.
  2. I like being in charge in my relationships. I guess I like knowing that I have more experience and confidence than my partner because then I’ll be able to make most of the decisions and sort of “lead” us. Most guys don’t like it when the woman leads, but I have this insatiable need to be the decision-maker (or at least be somewhat in charge) and I won’t be able to do that if I date a confident, cool guy.
  3. It makes me feel secure. Not only does it make me feel more secure in a self-esteem sense, but it also makes me feel secure in the relationship, meaning he’s less likely to cheat or want to end things because why would he when he’s dating someone way out of his league? He would probably do everything he can to keep me interested… at least in theory.
  4. I don’t like having to impress guys. The idea of running around trying to make sure the guy I’m dating still approves of me sounds seriously exhausting. I shouldn’t have to worry about being “good enough” for him, so if I date someone who’s way below my league, I can more or less trust that he won’t suddenly leave me for someone better because I’m the best he can do.
  5. It motivates me for some reason. Dating a loser just makes me want to be a better person for some reason. This sounds mean, but it’s truly not intended that way. I find myself looking for ways to be “better” than him but not to show him up, if that makes sense. I feel empowered to go ahead and be that amazing person I know I can be without worrying about an over-confident boyfriend trying to control me or tell me what to do.
  6. He’s smarter than me so it evens out. I might be more socially-savvy, but he’s actually very smart when it comes to facts and knowledge. He has his own skills and I have mine, so maybe we really are in each other’s league. We both have something about us that makes us extraordinary in the relationship.
  7. I’m good at building people up. I’m thinking that the reason why I tend to end up with “loser” types is that I look for people to improve or “fix.” I’m really good at showing other people why they’re amazing, complimenting them, and making them more confident. It’s no wonder why I end up with so many project guys.
  8. I know for sure they respect me. When you date a loser, you know that they likely respect you because you’re technically above their league. They’ll see past any mistakes you make and hold you in high regard. Who wouldn’t want that?
  9. I know I can do better, I just choose not to. So many of my friends will comment that I can do so much better, but why would I want to? I don’t need the stress of dating someone super hot or cool or successful or whatever. I don’t want to know that I could lose them to someone else. Dating a loser is comforting to me and it’s honestly, it’s better than dating a pretty boy, in my opinion.
  10. I’m sincerely physically attracted to them for some reason. I actually get all warm inside when I see a dopey loser-type who’s interested in me. I’m sincerely attracted to him, maybe partly because I feel sorry for him but I also think he’s cute in an “aw” sort of way.
  11. They make me seem more responsible to my parents. When you bring home a guy who seems to have his act together, your parents will fall in love with him and by default start pressuring you to keep up with him. If I bring home a loser, my parents would see me as having my life together compared to this sad, confused, immature guy.
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.