Online Dating: How to Start a Conversation

I received a ton of new messages this week and I’m ignoring most of them because they were fucking awful. None of them were unkind or crude, but a lack of effort put into the very first message sent to a complete stranger that you want to fuck is sad. Let’s go over a few guidelines for writing a decent message.

1. Ask a fucking question.

Hi How are you today ? I am moving to [nearby town] next week for my new job in a research lab. So, i am looking for new friends and people to hangout with. If you are interested, please reply and then we can talk further. Take care

Hello how are you doing? It’s nice to meet you I’m Chad :-) I was looking at your profile and thought it’d be nice to get to know you

“How are you,” is not a question, it’s filler and if I respond to it it’s going to be with a meaningless pleasantry that reveals nothing about my personality or how I’m actually doing. I’m not discouraging politeness, but take some initiative and make an effort to get to know the person you’re messaging. how to talk to people on an online dating siteThere’s nothing I hate more than carrying an entire conversation because the person I’m talking to is too lazy to contribute anything or even ask a question. If you want my attention, show a genuine interest in me. If it’s obvious that you’re copying and pasting the same message to every woman within a 25 mile radius, I’m not going to bother to reply.

It’s funny that you consider summer the off-season – I live for my summers. What do you do for fun now that you can’t ski?

This message let me talk about one of my favorite things and led to a conversation about how we prefer to spend our summers, which led to a date. That was the entire message, but he actually read my profile and asked a question that was relevant and required more than a one or two-word response. He started a conversation.

2. Ask what you want to know.

Hey there… just saw that you stopped by my profile, so I thought I’d say hi! Having any luck on here so far?

Does this guy really want to know how many dates I’ve been going on with people who aren’t him? No, this is the message of a man who wants to talk to me but has no idea what to say to an actual human woman. I use these questions quite often with decent results:

What are you reading?

Where are you from?

I want to know what someone is reading because it might give us something to talk about, or it might let me know right away that they don’t share one of my biggest interests. I ask where someone is from because most of the people in my area moved here from somewhere else, myself included, and I find the choices people made that brought them here interesting. In other words, I’m interested in their answers to my questions — I’m not just asking in hopes of getting any response at all.

3. Send brave messages.


So your profile leads me to believe that you’re intelligent and prone to thinking. Unsurprisingly, I like these things.

Normally I’d attempt to segue into some sort of tactful screening process, desperately hoping for some sort of sign that you’re not a serial killer, but in my experience, almost no one uses OkCupid for senseless violence so I’m going give you the benefit of the doubt.

Instead I’d like to invite you to a well-lit public location for small talk and snacks. I find that meeting someone is the best way to get to know them, but if your screening process is more rigorous than mine, I’m happy to exchange a few messages here.


The exact text of a message I sent on Monday. We’re going out on Friday. I let him know why I was interested in him, I showed my personality with the second paragraph, I got to the point but tried to be flexible if he wasn’t comfortable meeting a complete stranger. Meeting someone online really isn’t that hard. This is one of those situation where putting in a little effort can go a long way — ask a few questions, stay relevant and interested, and be brave enough to take the next step.

Share your messages both good and bad in the comments. What do you respond to? What makes you cringe to the delete button?

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