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When to Stop Messaging a Woman: The Gentleman’s Guide

When you should stop messaging

When a girl replies to a message, it’s a fucking victory. 

You spend so much time and energy searching OkCupid, reading profiles, and crafting good messages.  So when a girl finally replies, and you’re having an ongoing conversation, it feels like total success.  And it is!

But what if you ask her to meet…and she says, “not yet”?  What if you’re the only one keeping the conversation going?

Maybe she’s just looking for attention, or not really interested in meeting someone for real.  Don’t let her waste your time.  You deserve to find a girl who’s excited to meet you in person.

But after all that effort spent to get a reply, it can be hard to tell when you should stop messaging a girl.

Here are the common situations guys get stuck in.  They’re easy to identify and prevent:

1) You’re the ego-stroker.

How to tell it’s happening:  You’ve been messaging a girl for more than 2 weeks or 6 sent and returned messages.  Your messages are well-thought-out and funny.  You ask questions and keep the conversation going.  Basically, you’re being awesome at messaging.

She, on the other hand, writes minimal replies, doesn’t ask you any questions, and lets days pass between messages.

You’ve brought up meeting at least once, but she ignores your invitations, says she has other plans, or keeps saying she’s not ready.

What to do:  Move on. This lady-douche’s ego is already inflated, and you don’t need to make it any bigger.  If she had a real interest in meeting you, she would have agreed to it (or suggested an alternate time, or given a genuine reason why she didn’t want to meet yet).

What to say:  “Shit or get off the pot.”  And make it clear you’re getting off the pot.

A more polite but still decisive way of saying this: “Well, I’ve enjoyed getting to know you, but it seems like you’re not really interested in meeting.  Let me know if you are.  Otherwise, good luck on here.”

New course

2) You’re the hand-holder.

How to tell it’s happening:  You’re messaging a girl who seems really cool.  You’re both curious about each other, you’re both keeping the conversation going, and it seems like you’d have a great first date.

The only problem is, she says she isn’t “ready” to meet yet.

Maybe it’s her first foray into online dating and she’s a little nervous.  Or maybe she feels more comfortable opening up to someone in writing, rather than in person.

You feel like it’s a decent reason – but it’s been a few weeks of these (otherwise great) messages, and you’re not looking for a pen pal.

What to do:  First, decide how much longer you can handle messaging without meeting.  A week?  A month?

What to say:  Let her know you understand her concerns.  Say you’ve really enjoyed getting to know her, but want to make sure you both feel the chemistry in person.  Suggest a quick date (coffee, lunch) in a very public place.

She says, “Yes!”  Awesome!  Start planning the first date!

She says, “Not yet.”  Remember your time limit.  Tell her you’d really prefer to meet after X amount of time (whatever you decided), but ask what you can do to make her more comfortable.  You could show her you have nothing to hide by offering to friend her on Facebook, or ask if she wants to Skype, text, or talk on the phone.

When you’re closing in on that time limit, ask her again about the short date in a public place.

She says, “Still not ready.”  Politely, say something like this: “I understand your concerns, and I’d love to meet you when you’re ready.  But I’ve found it’s important to meet someone in person to see if we’re a good fit.  You and I have been having such a great time talking, I think we will be!  But like I said, I do understand if you’re not ready.  It seems like we each need to do what’s right for us.  I’ve really enjoyed getting to know you, so definitely get back in touch when you’re feeling more comfortable.”

If this doesn’t spur her into action, it’s time to move on to someone who’s psyched to meet you.

3) You’re doing ALL the work.

How to tell it’s happening:  You two have a lot in common, and you both genuinely seem to be enjoying each other’s messages.  The only problem is, you’re the only one keeping the conversation going by asking questions and bringing up new topics.  You’re beginning to feel like her conversational slave.

What to do:  First of all, it sounds like you’re a conversational winner!  Next, try to figure out if she’s just a little socially inept, or completely self-centered.

Would the messages grind to a halt if you didn’t ask her any more questions, or introduce new topics of conversation?  Put it to the test.  

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What to say:  Reply to her next message but don’t add more.  For example: say you asked her about a band you both like.  She answered your question, but didn’t ask you anything in return to continue the conversation.  So you do the same: “Yeah, I’m really excited for The Gaslight Anthem’s new album, too.  I’ve heard it’s gonna be pretty different stuff for them, so that’ll be cool.”

Don’t add anything else.  It’s up to her to think of something next.

What next:  If she replies with a new topic or a question, congratulations!  She probably just needed some prompting.  And – bonus! – she’s definitely interested in talking to you.

If she doesn’t say anything back?  Maybe she has nothing to talk about when she’s not talking about herself.  Maybe she’s not interested in making an effort to keep the conversation going.  Drop it like it’s hot.

(If you still have some effort left and still feel she’s worth meeting in person, suggest that.  But be prepared to keep the conversation going the whole date, too.)

4) You realize you don’t have anything in common.

How to tell it’s happening:  You start messaging a girl because she seems cool, but now you’re wracking your brain for stuff to talk about in every message.  Nothing she’s bringing up is clicking for you, either.

What to do:  Don’t waste any more time (for both your sakes).  It’s OK to feel a bit bummed, guilty, or even inconvenienced.  But this the point of dating: getting to know someone and deciding if you’re a fit.

However, she might be thinking things are going just fine.  So don’t do a slow fade or drop off the earth – that would confuse her and/or hurt her feelings.

What to say:  A polite goodbye.  It’s worked for me to say a version of this:  “I’ve really enjoyed getting to know you these past couple days/messages, and you seem like a great girl.  But unfortunately, I don’t think we’re a match.  Thank you for taking the time to get to know me, too.  I wish you all the best with your search!”

Sure, her ego may get a little bruised.  But I’ve found that most people will write back, appreciative for the heads-up, and wish me luck, too.  Nothing wrong with a little good karma!

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5) You just started seeing someone and want to focus on that.

Congratulations!  May you never haunt OkCupid again!

Before you log off, give a heads-up to any other girls you were messaging.  Sure, you didn’t make any promises here, but it’s polite to tell them what’s going on.

What to say:  A polite goodbye similar to: “I’ve really enjoyed getting to know you these past couple days/weeks/messages, and you seem like a great girl.  But I actually just started seeing someone, and I want to see where it goes.  Thank you for taking the time to get to know me, too.  I wish you all the best with your search!”

Most women will appreciate that you gave them a heads-up – even if they’re bummed to stop messaging you.

And BONUS:  If things don’t work out with the girl you’re seeing, the ones you had been talking to might be happy to pick up where you left off – especially knowing how classy you were the first time around!


It sucks to get stuck in a dud messaging situation.  These tips can help you figure out if the situation is worth saving and how to handle it.  Remember: you deserve to meet a woman who’s excited to meet you in person!


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