I’m An Overthinker Dating An Underthinker & It’s Hard AF

In my opinion, there’s nothing worse than someone who doesn’t think critically about things and just floats through life, letting the wind move them in any direction. Somehow, I ended up with a guy exactly like this. Instead of spending time researching, analyzing, and coming up with different outcomes for every situation like I do, my boyfriend “wings it” (his words, not mine) half the time and it’s the most frustrating thing ever. To say our relationship is a challenge is putting it lightly.

  1. He’s not very observant whereas nothing gets by me. As an overthinker, I’m naturally very observant and I see meaning in everything. My boyfriend doesn’t. He wouldn’t even notice a girl checking him out unless that girl was wearing a Ducks jersey, whereas I see and pay attention to everything. This is frustrating for me because I’m constantly yelling at him for being so completely unaware of his surroundings. Like, #STAYWOKE, dude.
  2. I’m always reading too much into his text messages and he doesn’t think twice about them. It was really hard for us in the beginning, or maybe it was just hard for me. I overanalyzed his text messages like it was nobody’s business. I’d lose sleep over the period he chose to put at the end of a sentence and it was honestly exhausting. Thankfully, once I was comfortable with him, I really opened up about what I needed him to do in terms of texting (which was complete sentences, clear emojis, and timeliness). Yes, I’m aware I sound crazy!
  3. He never second-guesses himself like I do. What I love about my boyfriend is that he’s confident as hell, but not in an arrogant sort of way. He just oozes self-assurance because he lives his life without much thought. He’s like HBO, you know? No limits. He doesn’t feel constrained by his mind like I do. He’s not worried so much about making the perfect decision because he doesn’t see one decision as being better than the other.
  4. I have an obsession with words but he doesn’t care which ones he uses to express himself. I’m an English major and so was my dad. Basically, an obsession with words runs in my family. I focus way too hard on the words people use and the overall syntax structure they use to deliver them. I can’t help it. Words are important and when my boyfriend uses a word that has a double meaning, yes, I’m going to drill him into elaborating on what the hell he’s saying.
  5. He lets go of everything pretty much immediately while I can hold a grudge. One of the many negatives of being an overthinker is that I have trouble letting things go. My boyfriend and I will fight and in a few minutes, he’s already ready to kiss and makeup. I can’t work like that. It takes me a while to get over something. I have to really talk it out before I feel confident enough that the issue is resolved. Thankfully, I have a patient guy who doesn’t mind when I spend hours talking about trigger words.
  6. I need to have everything organized but he flies by the seat of his pants. Going on a trip with my boyfriend is a roller coaster ride of emotions. Before the trip, I’m the one making all of the plans and getting all the ducks in a row. My boyfriend is the one randomly throwing out suggestions that I usually dismiss because they’re not reasonable or worth our time (I say in a very non-controlling way).
  7. He’s never in a rush but I need to be everywhere five minutes early. He’s always going with the flow. Seriously, I’ve never met anyone who’s never, EVER in a rush to do something. We’ll go to dinner a couple hours before a movie and I’ll start rushing, eating my food without chewing it because I’m so anxious about missing the movie. My boyfriend? He’ll order appetizers, entrees for days, and desserts. Time is the furthest thing on his mind.
  8. I want to know what makes people tick but he doesn’t seem to care either way. I’m a people watcher. I study the people I’m with and from there, I form a loose opinion of who they are. I thought it was common until I met my underthinker boyfriend whose lack of observation skills (and his complete disinterest in honing them) keeps him from caring too much about what everyone else is up to. That’s probably a good thing but it’s still pretty frustrating.
  9. He’s not afraid of anything while I have my reservations. My boyfriend doesn’t think, he just does. He’ll do anything twice. He’s not afraid to take risks and make BIG decisions based on how he’s feeling at that moment. It’s frustrating to watch someone not have to think for hours about whether or not they should quit their job and travel for a month (which, by the way, he did). I envy him more than anyone. I’m just not that carefree.
  10. I can rarely stay in the present but the future might as well not even exist to him. I’m constantly thinking in the future and sometimes even the past. When I first started dating my boyfriend, I spent a lot of time in my head going over how exactly we’d work long-term. Besides the fact that he’s an underthinker while I’m an overthinker, we didn’t have a ton in common. I almost broke up with him because I didn’t think marriage could ever be on the horizon. Turns out, I was wrong—not about the marriage part (at least I hope!) but about our compatibility. We’re extremely different but it works for us.
Jordan White is a writer based in Scottsdale, Arizona with more than 8 years of experience. She graduated from Northern Arizona University with a degree in Rhetoric and Creative Writing in 2015 and while there, she wrote for The Daily Wildcat. She has since written for sites including FanBread, and, of course, Bolde. You can find about more her on Facebook. She has a passion for giving her audience something to laugh about and despises the heat more than anything.