Don’t Send These 5 Texts If You Want a Second Date

Trust me, I know better than most people how difficult dating is today. I spent most of my 20s trying to navigate the ups and downs of the dating world. The self-doubt, the uncertainty, not to mention the manipulative partners and commitment-fearing daters—it all can get to be too much.

However, despite how intimidating dating can be today, there are some dos and don’ts when it comes to communicating early on, especially via texting.

Anita Fletcher, a sex and relationship expert at Fantasy Co., revealed the types of texts to avoid sending after a first date.

1. Frequent check-in texts 

Please don’t send messages like “You there?” “Hello?” “Guess you’re busy…” after the other person is clearly not interested in or too busy for the conversation. I once had a guy (who I had told I wasn’t interested) text me five times in the span of a day—without any responses from me in between.

“This text reveals anxiety about being ignored,” Fletcher explained. “It puts pressure on the other person to respond immediately, which feels suffocating in early dating.”

While you might have good intentions by checking in with the person you’re seeing, overdoing it with multiple messages in a row will only scare the other person away. 

“Triple texting demonstrates poor emotional regulation,” says Fletcher. “It suggests you’ll be high-maintenance in a relationship.”

Of course, this is completely different from someone actually expressing concern. For example, if you have plans with this person and haven’t heard from them in a few days, sure, send that follow-up text. But if you’ve only just met and demand their attention all throughout the day, well, you likely won’t be getting a second date anytime soon.

2. Demanding messages

Even worse than the triple check-in text is the “why aren’t you responding?” message, which is more common than you might think. 

“This message reveals deep insecurity and an inability to respect boundaries,” Fletcher said. “It’s manipulative and will make anyone run for the hills.”

If someone isn’t meeting your communication needs, you can tell them that in a respectful, grounded way. However, demanding someone be at your beck and call is merely not sustainable—especially so early on in a relationship. 

“Most people send needy texts because they’re operating from a place of fear—fear of abandonment, fear of rejection, or fear of not being good enough,” Fletcher said. “When someone doesn’t respond immediately, anxious attachers spiral into worst-case scenarios. They think silence means disinterest, when really the other person might just be in a meeting.”

3. Venting dumps

Look, we all need to vent after a long day. But sending an essay about why you’re miserable and all the unnecessary details can overwhelm the other person.

That’s not to say you can’t vent to your partner. Once you’re in an established relationship and have an actual connection with the other person, that’s a totally different dynamic.

“Early dating should be fun and light,” Fletcher said. “Save the heavy stuff for when you’ve built trust and rapport.”

4. Emotionally intense declarations

While it’s perfectly reasonable to tell your date that you had a great time and would love to see them again, you should probably avoid being too intimate too soon. Saying things like “I miss you” after just one meeting will likely turn some people away.

“This text implies you’re already emotionally dependent on someone you barely know,” Fletcher warned. “It’s too much, too fast.”

It’s flattering to hear that someone misses you, but in my experience, when someone tells you that after a first date, there’s usually an underlying desire to rush the beginning stages of a relationship. Instead, take your time getting to know the person.

5. Validation-seeking questions

Early on in dating, it’s totally normal to question whether someone is interested in you. However, that doesn’t mean you should go fishing for compliments or request reassurance off the bat.

Messages like, “Do you think I’m attractive?” or “You probably think I’m boring…” (which, yes, I have received before) can feel overwhelming. We don’t need to demonize insecurity; everyone struggles with it sometimes. However, it’s important to learn how to emotionally regulate so you’re not projecting onto the other person or making them responsible for your feelings.

Not to mention, “Confidence is attractive,” Fletcher said. “Constantly seeking validation suggests you don’t believe in your own worth.”

“My advice?” she continued. “Put down the phone and work on yourself. The best relationships happen when two complete people choose to share their lives, not when one person desperately clings to another for validation. Remember, the right person won’t need constant texts to remember you exist – and you won’t need constant reassurance that they care.”