Should I Send a Risky Text? The Complete Guide
- Kristen K
- May 1
- 4 min read
Updated: May 15

In today's fast-paced dating scene, sending messages has become as easy as a few taps on your phone. But not every text is created equal. Among them are risky texts, which can create excitement but also anxiety. What exactly is a risky text, and when is it a good idea to push send? This guide will help you navigate the tricky waters of risky texts, providing insights on when to take a chance and when to play it safe.
What is a Risky Text?
A risky text is a message that challenges the current boundaries of your relationship. It can involve flirting, sharing intimate feelings, or hinting at something serious. These texts can quicken your heartbeat, whether they ignite excitement or apprehension.
Context, timing, and relationship dynamics matter significantly when sending a risky text. They can vary from a light and playful meme to a heartfelt expression about the future of your relationship. For example, a light-hearted joke could lead to a deeper conversation about your feelings.
When Are Risky Texts Common?
Risky texts often appear at various stages of dating. Here are some common scenarios where you might feel tempted to hit send:
Early Flirting: After a few fun dates, flirting over text can become more personal and intimate. (Psst – learn how to keep a text convo going here)
Post-Date Excitement: Following an enjoyable outing, adrenaline can prompt a daring text.
Testing Boundaries: You may want to gauge your partner's openness to deepening the relationship.
Confessions of Feelings: Eventually, you might feel compelled to share your true feelings.
Long-Distance Relationships: Being far from your partner might lead you to send messages that strengthen your bond.
6 Times You Should Send a Risky Text
Here are five situations where sending a risky text could be beneficial:
When You’re Both Flirting: If your conversations are playful already, feel free to raise the stakes. A flirty reply can keep the momentum flowing.
After a Great Date: Sending a bold follow-up after a fantastic date can maintain the excitement. For instance, texting “Last night was a blast! I can’t stop smiling!” shows your interest.
When You Want to See Where They Stand: If you are curious about what your partner thinks about your relationship, a direct yet playful question like “So, are we more than just friends?” can help clarify things.
If You’re Ready to Share Feelings: After getting to know someone for several weeks, expressing your feelings can enhance your connection. A thoughtful message like “I really enjoy our time together, and I think I’m developing feelings for you” can be pivotal.
As a Fun Icebreaker: Especially early on, using humor in a risky text can spark a fun conversation. A cheeky message like “So, when are we getting married?” can lighten the mood and get laughter going.
It's Your Ex, and You Think it's Ok: If it's your ex and they haven't blocked you, tried to block you, have told you that they never want to speak to you again...it's probably alright. Question mark. HA!
Of course, anytime you're going to send a risky text is one of the best times to post Teatime, so don't forget to share it. ;)
6 Times You Shouldn't Send a Risky Text
On the flip side, there are clear times where refraining from sending a risky text makes sense:
When You’re Unsure About Their Feelings: If you are unsure how they feel, sending a risky message might create awkwardness. It’s wise to hold off until you’re more confident.
After a Heated Argument: In the aftermath of conflict, sending bold texts may escalate issues. Instead, focus on resolving disagreements first.
In a Moment of Jealousy: Jealousy can cloud your thinking. Avoid sending a risky text driven by insecurity, as it may lead to misunderstandings.
When You’ve Just Met: During initial encounters, keep things light. A risky text might scare the other person off if you haven’t built comfort yet.
If It's a Double Text: Of course, with double texts, they are not all bad but you should precide with caution to avoid annoying the other person. Learn about when to double text.
If it's Your Ex and You Are On VERY bad terms: Maybe you broke up with them over text. Or you previously rejected them unpolitely. You know more than I do. Just use that gut feeling
Thoughtful Considerations for Sending Risky Texts
Deciding whether to send a risky text requires careful thought. It is essential to consider your relationship's dynamic, emotional connections, and how the other person might respond.
The right text can evoke joy, deepen bonds, or spark essential conversations. According to a 2021 study, 70% of individuals felt more connected to their partners after sending a playful or flirty text. However, take care to avoid potential miscommunication or discomfort.
In the world of texting, it’s wise to listen to your instincts. Sometimes, pausing can be just as powerful as sending a message.
When the moment feels right, don’t hesitate to express yourself. Remember, taking a moment to reflect can yield significant benefits in your communication. Happy texting!
Got a text your not sure about? Post it to Teatime. You can download the Teatime app here or learn about What is Teatime here.