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9 People Reveal Their Most Awk Text Convos With Crushes & You'll Cringe

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When you're flirting IRL, a potentially weird moment can seamlessly become a super cute memory. With a playful hair flip or a sly smile, it can be easy to laugh off a joke that didn't land or a word you mispronounced. Of course, when texting comes into play, bouncing back from wording something wrong or saying something weird can feel totally daunting. So if you've ever felt like texting your crush is awkward, you're certainly not the only one.

When you don't know someone well, you may worry about how they're going to interpret your jokes or that they'll read a little too into your messages. Texting your crush can mean overthinking your words and feeling self-conscious about your sense of humor. Of course, you never need to censor or tailor who you are to fit the person you like. Though nervousness and awkward feelings are something everyone encounters from time to time, the right person will never make you feel bad for being who you are.

From sending a message to the wrong person to totally misreading the real meaning of a text, these eight stories about awkward texting will surely make you feel better about all the awkward encounters that have happened in your own inbox.


Short But Not Sweet
A super cute guy at a party came over and we ended up talking for two hours. Before he left, he came over to me to kiss my cheek and ask for my number. The next day I texted him something like, 'Nice meeting you last night. Let me know if you want to get a drink this week.' And he literally replied, 'It was a fun party.' I tried to keep the conversation going but it just... didn't.

— Kaya, 24

Mama Drama
I was messaging with someone on Tinder, and we agreed to meet up, so she gave me her number. I texted her 'Hi Jen, it’s Kyle!' But she responded, 'This is Paula, but there’s a Jen in my family, maybe you’re trying to reach her instead?' There was a typo in Jen’s number and she’d accidentally given me her mom’s number instead!

— Kyle, 31

Compliment Complications
I went out with friends and had a couple of drinks, then texted someone I had been on two dates with, 'You're so cute! I feel like I've been looking for you my whole life.' He responded three days later with, 'thanks.'

— Liz, 25

Group Message Messiness
My landlord's nephew had done some stuff around our house. I joked with my roommates that I thought he was super cute had a little crush on him. When I was at work one day my roommates ended up asking our landlord for the nephew's number without asking or telling me that they were doing so! Later in the day, the landlord started a group message with him, me, my roommates, and the nephew being like, 'So, John, you gonna ask Sara out?'

— Sara, 21

Emotional Emails
I met a really cute person at a work event. When I asked for their number, they were like, 'I don’t have a phone right now' and gave me their email. We went on a few dates, literally all coordinated by email (yikes), and then I didn't hear from them for a bit. A few days later, they wrote to me pretty late at night, 'This week is really busy. But where r u right now?' I just didn’t respond and probably never will. A booty email is just too awkward.

— Gemma, 23

I had liked someone for a while and we were starting to talk a lot. They sent me this long text out of the blue that was pretty vague but just felt off. I couldn't tell if I was getting rejected or not, so I waited a few days to reply just to give them some space. When I did reply, they were like 'I'm so happy to hear from you! I thought I said something wrong!' Which made me feel totally calm because they were just having a bad day when they sent the weird text. Eventually, I was like, 'I'd love to take you to dinner this week,' and they were like, 'Uh, I thought I made it clear that I didn't think we should see each other.' I felt like Anne Perkins in Parks and Recreation when she got dumped and didn't realize it.

— Morgan, 24

Cut Me Some Slack
I work at a small startup and we all Slack each other during the day. In a private chain, I asked my crush to go to a work party with me and he said 'Yes.' A minute later I got a notification from a group we're all in that was like, 'Kate just asked me to the holiday party and I said yes. I think I need to break up with Mara.' He didn't know that I was in that chain and I didn't know that he was dating someone named Mara.

— Kate, 26

Scout's Honor
My little brother is a boy scout. One time, he was telling me about a meeting he had and I made a joke about being in a church basement with a bunch of sweaty boys. Because the universe hates me, I was texting my crush at the same time and sent the "Boys in the basement" message to him by mistake. He was totally weirded out.

— Jenna, 24

No matter how long you've been crushing on someone, sometimes texting gets awkward. Dating can be totally nerve-racking, and getting stressed over the phone is completely natural. Of course, you never need to feel bad for making a goofy joke or sending the first message. If someone is put off by you being you, they're probably not the one for you and there's nothing awkward about that.

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