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Relationships & Dating

Navigating relationships as a teen can be exciting, confusing, and sometimes a little overwhelming — and that’s totally normal. Whether you’re figuring out how to talk to your crush, dealing with your first breakup, setting healthy boundaries, or just trying to understand your feelings, this space is here to guide you.

We cover everything from dating tips and friendship dynamics to recognizing toxic behavior and building self-respect. Whatever stage you’re at — single, dating, heartbroken, or just curious — you’ll find honest, supportive advice that helps you feel more confident in your choices and more connected to who you are.

Because relationships shouldn’t be stressful or scary — they should help you grow.

Teenagers are at a stage where their brains are still developing, especially the areas responsible for emotional regulation and impulse control. This makes teenage love feel all‑consuming and intense.
— Dr. Lisa Damour, clinical psychologist and author, speaking on the emotional intensity and developmental reality of teenage relationships
Flirting for Teens: How to Be Smooth Without the Cringe
Dating, Crush, Confidence Simon Richardson Dating, Crush, Confidence Simon Richardson

Flirting for Teens: How to Be Smooth Without the Cringe

You’re at school. You see your crush across the room. Your stomach flips, your palms sweat, and suddenly you forget how to speak like a normal human being. Sound familiar?

Let’s be real—flirting can feel like the most awkward thing in the world when you’re a teenager. The pressure to impress, the fear of looking silly, and the constant worry about rejection can make even the most confident teen freeze.

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12 Ways to Know If Someone Likes You Back (For Teens)
Crush, Dating Simon Richardson Crush, Dating Simon Richardson

12 Ways to Know If Someone Likes You Back (For Teens)

Wondering if your crush feels the same way about you? You're not alone. Figuring out whether someone likes you back can feel like trying to decode a secret language. But the truth is, most people give off small (and sometimes obvious!) signs when they’re into you.

Whether you're texting late into the night, catching glances in class, or just trying to make sense of mixed signals, these 12 signs can help you spot the difference between friendliness and full-on flirting.

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What to Wear, Say, and Do on a First Date
Dating Simon Richardson Dating Simon Richardson

What to Wear, Say, and Do on a First Date

First dates can be both exciting and terrifying. You’re probably wondering: What should I wear? What do I say? What if things get awkward? Don’t worry—you’re not alone. Everyone feels nervous before a first date, especially if it's your first ever date.

This guide covers what to wear, say, and do on a first date—plus tips to keep your cool and be yourself.

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What to Text Your Crush: Conversation Starters and Mistakes to Avoid
Crush, Dating, Communication Simon Richardson Crush, Dating, Communication Simon Richardson

What to Text Your Crush: Conversation Starters and Mistakes to Avoid

Texting your crush can feel like a high-stakes game. One wrong emoji and it’s game over. But don’t stress—whether you’re texting for the first time or trying to keep a convo going, this guide will help you send texts that feel natural, confident, and totally you.

We’ll break down the best ways to start a conversation, how to keep things going, and the major texting mistakes to avoid—plus what to do if they don’t reply.

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Teen Dating Tips: How to Start Without Feeling Awkward
Dating Simon Richardson Dating Simon Richardson

Teen Dating Tips: How to Start Without Feeling Awkward

Starting to date as a teenager can feel like stepping into a world you’ve never been trained for—full of nervous butterflies, mixed signals, and moments where you just don’t know what to say. But guess what? You’re not alone.

Feeling awkward is totally normal. Whether you’ve got a major crush, you're thinking about asking someone out, or you're just curious about what dating is even like, this guide will help you start with confidence—and way less cringe.

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A Guide to Teen Dating: What to Expect and How to Start
Dating, Relationships Simon Richardson Dating, Relationships Simon Richardson

A Guide to Teen Dating: What to Expect and How to Start

Dating is an exciting part of teenage life, but it can also feel confusing, nerve-wracking, or even overwhelming—especially if you're just starting out. Whether you're thinking about asking someone out, going on your first date, or just wondering what dating actually means, you're not alone.

This guide will walk you through what teen dating looks like, how to know if you're ready, what to expect, and how to keep things fun, healthy, and respectful.

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What to Do on a First Date: Fun and Safe Ideas
Dating Simon Richardson Dating Simon Richardson

What to Do on a First Date: Fun and Safe Ideas

First dates can be exciting, awkward, nerve-wracking—and totally unforgettable. If you’re a teen stepping into the world of dating for the first time, you might be wondering: Where should we go? What should we do? And how do I stay safe?

This guide is here to help. Whether you're shy or super social, tight on money or just unsure what counts as a “good” first date, we’ve got you covered with fun, safe, and low-pressure ideas that work for just about anyone.

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How to Ask Someone Out Without Feeling Awkward
Dating, Confidence, Vulnerability Simon Richardson Dating, Confidence, Vulnerability Simon Richardson

How to Ask Someone Out Without Feeling Awkward

Asking someone out can feel terrifying. Your palms sweat, your heart races, and a million “what ifs” crowd your brain. But here’s the truth: feeling awkward is totally normal, especially when you’re putting yourself out there. Whether it’s your first time or your fiftieth, that mix of nerves and excitement is part of the process. The good news? There are real ways to make it easier—and even feel good doing it.

In this post, we’ll walk you through how to ask someone out with confidence, what to say, how to reduce the awkwardness, and what to do afterward—no cringe, just real talk.

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