Author: Jessica Lowe

Picture this. You’re texting a guy you’re into and the conversation has gone stale. You’re both just typing “haha yeah” back and forth like a couple of robots running out of battery. We’ve all been there, staring at our phone, trying to think of something that doesn’t sound like small talk from a job interview. Enter the this or that question. It’s simple. It’s fun. And it works better than any “hey, how’s your day going” text ever could. Here’s why this or that questions are basically magic. They force a quick answer, which means less overthinking and more real…

Picture this. It’s 9pm, you’re in your pajamas, and your boyfriend is three time zones away eating what he swears is “just a snack” but is definitely dinner number two. You’ve already sent the good morning text, the goodnight text, and one blurry photo of your cat doing nothing interesting. Now what? This is the long distance struggle nobody warns you about. The conversation dies not because the love does, but because you run out of things to say. Texting “how’s your day” on repeat gets old fast, for both of you. That is where texting games come in. They…

My boyfriend and I once spent an entire Tuesday texting each other made up movie titles based on our relationship. “The Guy Who Steals All the Blankets” was a personal favorite. We laughed so hard I almost dropped my phone in my coffee. That silly game reminded me why texting still matters, even when you see each other every day. A good text game is not about filling silence. It is about staying curious about someone you already know well. Couples get comfortable, and comfortable can turn into autopilot if you let it. That is where these 53 games come…

You know that text thread that’s turned into a graveyard of “lol” and “haha ok”? Yeah. Mine did that once for an entire week. My boyfriend and I had somehow downgraded from actual conversations to sending each other memes and calling it bonding. Riveting stuff. That’s when I discovered question games. Not the cheesy “if you were a tree, what tree would you be” kind. I mean real, fun, sometimes cheeky questions that make him actually put his phone down and type back more than three words. Here’s the thing. Guys aren’t always great at starting deep or playful chats…

Last week my boyfriend and I sat in total silence for ten minutes because neither of us had anything new to say. Ten minutes. On a Tuesday. That is when I panicked and blurted out, “okay but if you had to fight one animal the size of a horse, which one.” Suddenly we were both laughing, arguing about whether a horse sized golden retriever would even attack, and the silence was gone. That is the magic of a good hypothetical question. It skips the boring “how was your day” loop and goes straight to the fun stuff. You learn what…

So there I was, three months into dating someone, convinced we were basically soulmates. Then I asked him one random question over tacos. What’s something you’re scared of that nobody knows about. His answer floored me. Turns out I knew his coffee order but nothing about his actual insides. That’s the thing about relationships. We learn the surface stuff fast. Favorite pizza topping, phone lock screen, that one friend he complains about. But the deep stuff only comes out if you actually ask. That’s where these questions come in. 45 of them, split into five categories, built to get past…

You know that moment when you’re staring at your crush’s name in your messages app, thumb hovering, brain totally blank? Yeah, me too. Last month I spent ten minutes typing and deleting “hey” like it was a legal document. Ten minutes. For one word. Here’s the truth. Small talk is boring and your crush is probably tired of “how’s your day going.” You want something that makes him smile, makes him think, and maybe makes him blush a little. That’s where flirty questions come in. These 52 questions are built to spark real conversation, not just a “lol yeah” and…

Picture this. My boyfriend and I were three glasses of wine into a “quiet night in” when I asked him what his weirdest turn on was. His face went red. Mine did too. Ten minutes later we were laughing so hard we forgot we were supposed to be watching a movie. That night taught me something. The right question can do more for your love life than any fancy dinner ever could. We get stuck in a texting rut. “How was your day.” “Good, you?” Boring. Predictable. A total spark killer. But swap those tired questions for something naughty and…

Picture this. You and your boyfriend are on the couch, phones out, half watching a show neither of you is actually watching. Sound familiar? I once spent an entire Friday night in that exact spot until I finally asked him what his most embarrassing childhood nickname was. Turns out it was “Turtle” because he wore a green backpack every single day for three years. We laughed so hard I almost fell off the couch. That one question turned a boring night into one of our favorite memories. That is the power of a good question. It is not about being…

Picture this. You and your boyfriend are on the couch, both scrolling your phones, and somehow you know more about a stranger’s vacation photos than what he’s actually dreaming about in life. Sound familiar? I once realized I knew my boyfriend’s coffee order down to the exact number of sugars, but had no idea what scared him. We’d been together a year. A year of oat milk lattes and zero real talk. That’s the thing about relationships. Comfort sneaks in, and somewhere along the way, curiosity takes a nap. It’s not that you love him less. You’re just busy. Life…