HELP! Texting Is Ruining My Dating Life

He’s probably working out right now. Or napping. Maybe his phone died? Or was I trying to be too quirky? Too forward? But I should be myself, right?

I’ve spent way too much time of my life making these justifications, second-guessing myself, stressing out and feeling sad…over text messages. Text messages.

I’m not a dating expert, but one thing I do know is that texting is only making it harder. Sure texting can be great. It allows us to stay in touch with our far away friends. It makes it easy to send directions, information, and last minute invites. We can send pictures and videos in an instant, and send a quick “thinking of you” note when we don’t have the time to call.

But what it gives us in convenience, it lacks in sincerity.

When it comes to dating someone new, which can be nerve-wracking on its own, texting adds a level of insecurity, allows both parties to flake on plans, backspace their real thoughts and introduces the grey bubble stress we all fear. (You know the “oh my gosh he’s typing back!” bubbles that pop up on your phone, only to receive a non-descript “sounds good.”)

Now I pride myself on being a pretty confident person. I’ll rock my cheetah pants and dark purple lipstick, I’ll pretty much talk to anyone, I’ll sing and dance on the subway, and for the most part I don’t really think too much about what people think of me. But I’ve watched all that confidence literally melt away because of texting-related situations. A little line of a few words on my phone screen (or lack thereof) can take me from “I’m wearing my cheetah pants!”, to “pass the Cheetos I’m staying in tonight”. And you know what – nothing should ever do that. But the fact is, we let it.

text quote 2

Let’s look at some real-life examples that have led me to my current feelings on texting:


Scenario #1

My older sister had been suggesting that I go on a date with this guy we went to college with. I brushed it off for awhile, but then I coincidentally ran into him at a local bar one night, we talked for an hour, exchanged numbers and in my mind “hit it off”. “Maybe I should pursue this”, I thought. So I decided to text him, asking if he’d like to grab a drink sometime.

Our conversation:

text message 1


Note the time between the text messages. A week. A FULL WEEK!

I didn’t think anything of asking him to grab a drink – girls can ask guys out. It’s not even “progressive” in my mind. I truly believe that when it comes to dating, it’s just as much of a girl’s responsibility to initiate plans (but again, no dating expert here).

But imagine what’s going through my head during that week. Did I scare him off? Was that too forward? Did we actually not have that great of a time when we saw each other the other night? Did I say something weird? Was it my hair?

My confidence was shot. And I invalidated the experience we had before. I let myself think I “made it all up”.

He just left me hanging. And texting allows us to do that. We keep things open-ended cause we don’t want to hurt people’s feelings. How many times have you texted a friend “I’ll try and stop by!” when you know you can’t.

Texting him definitely made it easy and less scary on me than giving him a call, but it also made it too easy for him to be wishy washy.

Maybe he actually was really busy, or was dating someone else, or just didn’t want to grab a drink – which is totally fine.

Scenario #2

In college I met a guy through mutual friends right before Christmas and starting talking to (“texting”) him over winter break. He was so fun to talk to, interesting and intellectual, had really cool glasses (I’m a sucker for guys in glasses), and we made a bunch of plans of fun things to do when we got back to school.

Long story short when we got back, I was trying to get together and follow through on our plans, but he’d had a sudden change of heart. Maybe it was commitment issues, maybe he just realized he was too busy, but when he texted me the “rejection text”, this horrible, awful thing happened.

text message 2


No your eyes aren’t deceiving you. I texted him back exactly what he’d said to me. And yes, it was because I was copying it to send to my best friend to be like “oh my gosh what do I say back?!” – but without even noticing, copied it, pasted it and sent it right back to him. Oh don’t act like you don’t do the same thing with your best friend.

quote 3But this situation illustrates two big issues that happen with texting and dating. One being that we make all these plans we don’t follow through with. Because texting gives us an easy out of situations, we make plans for more situations than we actually intend on following through with. When I’m interested in someone and they make plans with me, I set aside time. I get my hopes up, and when they don’t follow through, I’m let down.

Another issue is that texting gives us this need, and ability, to have a second opinion on everything we say. In real life, you can’t just stop your conversation, call your bestie and have them weigh in before you respond. We shouldn’t be so afraid to just say what we’re feeling. If we’re only saying what we think the other person wants to hear, then aren’t we just in a dishonest relationship?

It’s better to be honest and realize that hey, maybe you’re just not the right fit for each other than to try so hard to please them.

Side note: I survived this incredibly embarrassing situation and am actually really close friends with the guy. So see, it’s not all so awful.


At the start of a relationship, I like phone calls. I like talking face-to-face. I like seeing someone for who they are and not making up this ideal of who I think they are over text message conversations. And I’d rather have someone say no to me then
texting quote 11to make me sit around for a week and feel bad about myself. Yeah it’s nerve-wracking. Your heart races more. You don’t have the ability to backspace your words once you say them. But that’s how I think dating interaction should be. It shouldn’t be planned out or whenever it feels convenient to respond. It should be real. Real emotions, real feelings, real responses, in real time.

That’s why I’m going to stop punching the keypad so much. I’m going to pick up the phone and make plans. And I’m going to follow through with those plans and not text my way out of them (hopefully they’ll do the same for me). It’s scary, I know. Saying it is easy – actually doing it is another story.

But what’s scarier to me is that our generation is losing touch – literally. We’re not investing time in our relationships as much because we don’t actually need to see people. We can stay connected through our phones. Maybe we’ll only slip further into this, or maybe our generation will be the ones to backlash and realize the importance of face-to-face interaction, being brave enough to step out of our texting comfort zones and starting relationships the “old-fashioned” way. I can only hope that the latter will happen.

Let’s make the effort to just be with the people we care about most. It’s time to stop hiding behind our iPhones.

You up for the challenge?

Molly Longest

Co-founder, Creative Director Her heart belongs to: leather jackets, live music, Moscow Mules and getting that perfect picture Her guilty pleasures: frequenting the taco truck down the street a minimum of two times a week and talking to strangers' dogs in Central Park

  1. I totally feel you on this. I hate dating so much nowadays because of this exact problem. With texting, it’s so easy for people to just string you along or for miscommunications to occur. It’s also easier to either 1. avoid the “talk” or 2. reject someone. Texting (among other things) is ruining the dating culture and it really does suck. I have do feel that more people are taking note of this problem, though, so hopefully things start to change. Until then I’ll just be patiently (sarcasm) waiting by my phone for that text back. Ha -_-

    1. Hey Valerie!

      Thank you so much for your sweet comment. It’s always great to know that other people agree with this and feel the same way. xo

  2. Molly-
    I absolutely love this. I can’t tell you how many time that my obsessing over texting situations has ruined my day. And WHY? Usually I’m pretty go with the flow but I have just really come to hate how texting guys makes me feel. I’m officially going to try your advice and put down this stupid phone!


  3. I totally agree with is. I deleted my Facebook account because I got tired of how impersonal it is. I sometimes wish I didn’t have a cell phone. I remember my first girl I had a crush on and she liked me back. I would go over over to her house to see if she was home. I’d get so excited hoping that she would be there. If not id go play basketball and try back later. Now we know where everyone is every second of the day. There’s no mystery. I miss the way things used to be, before social media.

  4. This is spot on for any age! I am so glad that I came across this. I feel and believe that I AM pretty, sexy, and intelligent! At my age, damn tell me something NEW or at least create a new line. I enjoy talking with someone, let me HEAR them, not read them. Call me!

    Texting is lazy communication…it has its place, but not in a TRUE relationship or one that’s just beginning. A text can end it before it begins.

    Thanks for writing this article….Ladies don’t text him….it doesn’t determine a damn thing. You are worth a phone call.


  5. I’m so glad I found this article. I’m new to dating and have been in a textationship with this guy. I’ve asked him out on several occasions and we make the plans and he backs out last minute. I know I’m to nice and pretty to be wasting my time. These texts are killing my selfesteem! Ivery thought all those things you posted in your article. Ridiculous to let this laziness continue. I’m great at open communication, I won’t allow this any longer. Thanks for the girl power pep talk! Haha

  6. Oh, so true! I text my friends and family. Guys, if they have enough courage to call me to set up a date, that says a lot about them. If not, that says a lot about them as well. I know I had a few “interests”; but their lack of conversational skills landed them in the friend zone, and then they still text periodically to see what or how I’m doing. Sometimes I reply- depending on what I’m doing, but generally, I won’t text back until a lot later or not at all. Men who are potential interests are that for a reason. Why waste my time on someone who doesn’t have enough respect to call and only texts? Says a lot about his character. If you can’t handle a cheetah- then don’t bother with one.

  7. I was having same issues with texting guys , your article is so good I really liked it , texting just gives you headache and waste you time. I totally agree with you .
    I just have one question: are you an Aries woman by anychance? I am one too , and I always seem to make first moves and plans.
    Thank you for writing such a good article 😀

    1. Hey Assia!

      Thanks so much for your comment. I’m actually a Scorpio, but I find astrological signs fascinating! Maybe it’s a trait of both Scorpios and Aries?!

  8. As someone who is in a happy relationship (long distance when we aren’t at uni together) I can honestly say that texting is a huge deal of stress for me. I like texting, but my girlfriend doesn’t and sometimes unintentionally forgets to reply. As someone who is very anxious, this stresses me out constantly. I’m scared I annoy her, but I know this is not the case. Only recently I have realized that texting isn’t the end of the world… And my gf and I prefer real life interactions and stuff like Skype anyway, and she’s just bad at texting. But that doesn’t mean I’m not going to send her pictures of cute cats all day! ❤

    1. I totally feel you Andrea! I know I’m guilty of sometimes forgetting to text people back, but when you’re on the other side of things it can be stressful. But you’re so right, it’s not the end of the world. Keep doing your thing and sending those cat pics! Cause who doesn’t love that?! xo

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