Author: Jessica Lowe

Last week I asked my boyfriend what animal he’d be if he had to fight a raccoon for survival skills. He thought about it for way too long, then said “a very angry goose.” I have not stopped laughing since. That’s the power of a silly question. It turns a normal Tuesday into a story you’ll retell at dinner parties. Here’s the thing about silly questions. They cut through the small talk fast. No more “how was your day.” Instead you get real answers, weird answers, the kind that show you who he actually is underneath the polished first-date version.…

So there I was, three months into dating someone, still not knowing his middle name. We talked about pizza toppings for an hour but never touched anything real. Sound familiar? Here’s the thing. Trust doesn’t just show up one day like a surprise bouquet. You build it, one honest question at a time. And no, this doesn’t mean grilling him like he’s on trial. It means asking the stuff that actually matters, the stuff that makes him go “huh, nobody’s ever asked me that before.” That’s what this list is for. 53 questions that dig past the small talk and…

We have all been there. You are sitting on the couch with your guy, the TV is on mute, and you both run out of things to say. I once asked my guy if he would fight one horse sized duck or ten duck sized horses. Three hours later, we were arguing about duck anatomy and drawing battle strategies on napkins. That goofy moment saved our date night from total boredom. Hypothetical questions are my favorite secret weapon for couples. They skip the boring small talk about work or the weather. Instead, they unlock how his brain works, what he…

We have all been there. You are staring at your phone, tapping your chin, and trying to think of something to say that does not sound like a job interview. Last Tuesday, I tried to act cool and text a guy I liked. I meant to ask about his day, but my hands slipped and I asked if he preferred soup or salad in the event of a zombie apocalypse. He answered in two seconds, and we laughed for an hour. A simple, sweet question can totally change your vibe. It breaks the ice. It brings down his guard. Best…

We have all been there. You are sitting across from your man at a nice restaurant. The food is great. The lighting is low. Suddenly you realize you have been talking about your grocery list or his boss for twenty minutes. The spark is still there, but the conversation is stuck on repeat. I once asked my boyfriend what his dream superpower was just to break a silent dinner. Turns out he had a whole fifteen-minute plan for using telekinesis to grab snacks from the fridge. It turned a totally normal night into our funniest memory that month. That is…

You are sitting on your couch. You have your phone in one hand and a half-eaten snack in the other. You want to text your guy, but typing “Hey, what are you doing?” feels so boring. I have been there! Once, I tried to send a clever text, made a total typo, and spent ten minutes panicking over my phone screen. We have all done it. Texting should not feel like work. It should be fun! That is why I put together this list of tricky, playful questions. These questions will catch him off guard, make him laugh, and keep…

We have all been there. You are sitting on the couch with your guy, Netflix is playing in the background, and you realize you have run out of things to talk about. I remember one date night with my guy where we spent twenty minutes arguing about whether hot dogs are sandwiches. It was funny, but I realized I did not actually know his deeper thoughts. I knew his favorite pizza topping, but I had no clue what he wanted out of life. You do not need to conduct a formal job interview to figure him out. You just need…

Picture this. You’re on the couch, half watching a show, half scrolling your phone, and your boyfriend says “what are you thinking about.” You almost say “nothing,” because that’s the safe answer. But you don’t. You ask him something juicy instead, and suddenly the show is forgotten and you two are talking for an hour. That’s the power of one good question. Most couples run on autopilot. “How was your day.” “Did you eat.” “What do you want for dinner.” Nothing wrong with that, but it’s not exactly setting anyone’s pulse racing. The right question can crack open a whole new…

So there I was, three years into dating my last boyfriend, and I realized I had no idea what his biggest fear was. We knew each other’s coffee orders. We knew which one of us hogged the blanket. But his actual fears? Blank stare. Turns out you can share a bed for years and still skip the good stuff. That’s the thing about relationships. Comfortable doesn’t always mean close. You can fall into a routine of “how was work” and “what do you want for dinner” and forget there’s a whole person sitting across from you with dreams, weird childhood…

Picture this. You and your boyfriend are sitting on the couch, staring at your phones, and the silence is so loud you can hear the fridge humming. Sound familiar? I once asked my boyfriend what animal he’d be if he lost a bet, and twenty minutes later we were both crying laughing over his answer. A raccoon. He said raccoon. No context. Just chaos. That’s the magic of a good funny question. It turns a boring night into an inside joke you’ll bring up for years. It shows him you’re fun to be around, not just easy to talk to.…