Dating texting guide

What do you say when a guy says tell me about yourself

What to say when a guy says tell me about yourself. Examples of how to answer, what to skip, and how to keep the conversation moving.

Read the situation

"Tell me about yourself" is a wide-open prompt, and most people answer it like a job interview. They list their job, their city, and their hobbies in order, and it reads like a CV. That gives him nothing to pick up. He's usually asking because he wants a thread to pull, not because he needs the full story.

A good answer gives him two or three real things about you and one thing that invites a follow-up. You want to hand him a question he actually wants to answer. Give him a topic he cares about and the conversation starts moving on its own.

Keep it short enough to feel like a text, not a speech. Anything longer than a few sentences sounds like you're reading off notes, and he'll feel like he has to sit through it.

A boring opener next to the reply WingAI writes instead
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He wants a hook, not your biography

When he sends this, he probably has your profile open already. He's seen your job, your photos, and maybe a line or two you wrote. What he doesn't have is a sense of how you talk and what you're into when nobody's grading you. So the question is really a request for a way in. Read your own profile before you reply and notice what he's already seen. Then pick something the profile didn't say, or say the same thing with more personality, so he can tell you're a person and not a template.

If you go blank, look at what you've been talking about with friends lately or what you've been obsessing over. People answer this best when they're describing something they're currently into, because they sound like themselves and not like a form.

Pick the one detail that has a follow-up

A good reply usually has one thread he can grab. Some answers have no thread at all: "I work in marketing, I like hiking, I have two cats." Each fact is fine, but none of them asks for anything back. Compare that with a reply that mentions one odd or specific thing, like how you're trying to bake bread that doesn't collapse, or that you just got back from somewhere you hadn't planned to go. That gives him a question he'd naturally want to ask.

The test is simple. Read your draft and ask whether he could reply with a real question about one of the things you wrote. If he could only say "nice" or "cool," the answer is too flat. Cut the list down and keep the detail that has room in it.

Send it while the thread is still warm

This message tends to come in the first day or two after matching, so timing matters more than people think. If he sends it at night, reply the same day rather than waiting until the next morning, when the moment has gone a bit stale. A reply within a few hours reads as interest. One the following afternoon reads as you having thought about it and decided he isn't a priority.

If you get a short answer back, don't panic and don't send three messages in a row. Give it a day. If he hasn't come back after two days of silence, the conversation probably ran out of steam, and that's fine. You can let it go without any drama.

Do not send

Why these replies fail

  • “I'm 28, I work in HR, I'm from Leeds but live in Manchester now, I love travelling and running and trying new restaurants, and I have a dog named Biscuit. What about you?”

    It's a full CV with nothing to grab onto, and the "what about you" hands him the work of starting the next topic.

  • “Not much really, I'm pretty boring haha”

    It shuts the door and asks him to reassure you, which makes him do the work of finding something interesting in you.

  • “Honestly I'm still figuring that out, lol. What do you want to know?”

    It turns a simple question into a test of what he should ask, and most people won't know how to respond to that.

Avoid these

Common mistakes

  • Listing your job, city, and hobbies in the same order they appear on your profile
  • Writing a paragraph that covers your whole life, so there's nothing left for him to ask about
  • Turning it back on him right away with "what about you" and no content of your own first
  • Answering with "not much, just chilling" which closes the thread instead of opening it
  • Saying something self-deprecating about being boring, which makes him reassure you

Questions people ask

How long should my answer be when he asks tell me about yourself?
Two to four sentences is usually right. That's long enough to give him something specific and short enough to feel like a text. If you find yourself writing a paragraph, you're probably covering too much ground, so cut it down to the one or two things you actually want him to ask about.
Should I ask him the same question back?
You can, but do it after you've given him something real. If you only ask "what about you" with nothing else in the message, you leave him to do all the work. Share one thing first, then ask him something about his life that connects to what you said.
What if I really don't know what to say about myself?
Pick the last thing that made you laugh or annoyed you this week and describe it in a sentence. That's almost always more interesting than a summary of your life. People tend to sound more like themselves when they're reacting to something than when they're describing themselves in general.
Is it a bad sign if he asks this instead of something more specific?
Not really. Lots of people send it because they haven't got a better opener yet, and it's a normal first message on an app. It only becomes a concern if the conversation never moves past these generic exchanges after several back and forths. At that point, notice whether he's asking you anything specific at all.

What people say after using WingAI

  • “I overthink every text. Having three options and picking the one that sounds like me cut that spiral short.”

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  • “Used it for a couple hours and set up a date the same night. Not even kidding.”

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