Author: Jessica Lowe

We have all been there. You are sitting on the couch with your guy. The TV is playing in the background. You look at him and realize you have run out of small talk. You already know his favorite pizza topping and his hated movie trope. You want to get past the surface stuff and really know what makes him tick. I remember trying to get my ex to open up years ago. I asked him a super deep question right while he was playing a video game. He looked at me like I had two heads and went back…

It is 2:00 AM. You are staring at your screen. He is still awake too. You want to move past the usual small talk. Asking him about his favorite color feels boring. I once asked a guy his favorite cereal at 2 AM. He answered, but the spark completely died right there. We can definitely do better than breakfast food. Late night is the best time for real connection. The world is quiet. Guards are down. People share secrets they hide during the day. Deep questions help you skip the fluff. They show you how his mind works. You learn…

Picture this. You’re three dates deep and you still only know his coffee order and that he “loves hiking” (translation: went once in 2019). Small talk is fine, but it gets old fast. I once dated a guy for two months before I found out he was terrified of birds. Two months! We could’ve bonded over that on date one. That’s the thing about deep questions. They skip the boring stuff and get you to the good stuff, the stuff that actually tells you if you two click. Real connection happens in the details, not the small talk. This list…

Picture this. You and your partner are three episodes deep into a show neither of you even likes anymore. The silence isn’t bad. It’s just quiet. Comfortable. And also a little empty. That was me last month. My boyfriend and I had turned into roommates who occasionally held hands. So I did something wild. I put down the remote and asked him a real question. Not “how was your day.” An actual question. His answer surprised me. Mine surprised him back. That’s the thing about good questions. They crack open doors you forgot were even there. This list has 38…

Picture this. You and your partner are sitting across from each other at your favorite restaurant, and after ordering, silence hits. You both just stare at the breadbasket like it holds the secrets of the universe. Sound familiar? We’ve all been there, staring at our menus longer than necessary just to avoid the awkward quiet. The truth is, even happy couples run out of things to say sometimes. Life gets busy, and talking turns into logistics. Who’s picking up the dry cleaning? Did you pay the electric bill? That’s where these questions come in. They’re designed to pull you out…

Last month my boyfriend and I sat on the couch, both scrolling our phones, and I realized we hadn’t actually talked in two days. Two days. We live together. That’s when I made him put his phone down and asked him one question. “Are we doing okay?” He looked at me like I’d asked him to solve a math problem. Turns out we were fine. We just needed to say it out loud. That’s the thing about relationships. You can love someone deeply and still forget to check in. Life gets busy. Netflix gets loud. And suddenly a week goes…

I once dated a guy for four months before I found out he still lived with his ex. Not “we’re just roommates for the lease.” Actual, current, sleeping down the hall ex. I found out from his cousin at a barbecue, while holding a hot dog, in front of everyone. That’s the day I learned the hard way that vibes are not a vetting process. You can have amazing chemistry and still be walking into a mess. The fix isn’t a background check. It’s just talking. Real talk, early talk, before your heart is too involved to think straight. That’s…

I once dated a guy for four months before I found out he still lived with his ex. Not “we’re finalizing paperwork” lived with her. Full on shared Netflix, shared fridge, shared everything. I found out at a birthday party when she showed up and casually mentioned she needed him to grab milk on his way home. To their home. Cool cool cool. That’s the moment I learned the hard way. Chemistry tells you nothing. A few good dates tell you nothing. If you want to know who you’re really dealing with, you have to ask. This article is your…

Picture this. It’s 9pm, you’re in sweatpants, and you’ve rewatched the same three seconds of his last video call just to hear his laugh again. Relatable? I once texted my long distance boyfriend “I miss you” seventeen times in one week and then panicked that I sounded clingy. Spoiler, I did not sound clingy. I sounded like a woman in love who lived four states away from her person. Long distance is hard. Nobody warns you that missing someone can feel like an actual physical ache, right in your chest, usually at the worst possible moment like during a work…

We have all been there. You are sitting on the couch, staring at the back of your boyfriend’s head while he plays video games, wondering what is actually going on in his mind. Is he thinking about your future together, or is he just thinking about pizza? Sometimes hints and passive-aggressive comments do not cut it. You need real answers, and you need them now. I once spent three weeks dropping subtle hints about moving in together. I left apartment listings on the kitchen counter. I mentioned how cute his dog would look in my living room. Do you know…