How to Suggest Meeting and Get a Date

Hey Em,

How long do I have to message a girl before asking her to meet me in person? I don’t want to freak her out by asking too soon. But I don’t want to keep messaging forever.

When’s the right time, and what’s the best way to suggest meeting?
— Luke

Luke, you are not alone!  I’ve noticed a ton of guys are unsure about how/when to ask a girl to meet. 

This is a critical moment in online dating, and it tends to fall on the guy’s shoulders.  Wait too long, she might go out with another guy...  But ask too soon, or say the wrong thing, and you’ll seem like an eager rapist, right?

Meeting in person is the whole point of online dating. 

We need to know if we have chemistry in person!  If she’s replying to your messages, and asking you about yourself, then she’s definitely thinking about meeting you, too. 

Here’s how to know if the timing is right, and two ways to ask her out:

1) Put in your time. 

The Timing: 
A good benchmark is three to four messages, per person.  If your messages are short – two or three quick lines – then wait a couple messages more.  If both your messages have been long – three or four solid paragraphs – then you’re good to go.

Say you’ve been messaging this girl almost every day this week.  The conversation is flowing.  You’re asking her questions, and she’s showing interest in getting to know you, too.  It’s time.

How to Ask Her Out: 
At the end of a message, simply say something like, “I’m really enjoying talking to you.  Would you be interested in meeting for a drink sometime this week?” 

Some guys cover their bases by adding, “Obviously, if you’re not ready to meet yet, I’m happy to keep messaging a little while longer, too." This is a gentlemanly touch, but not completely necessary.

When this guy asked me out, it was simple, direct, and polite. I said yes!

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If she says yes, then congratulations!  YOU WIN!  Lock in the date!

If she says, “No,” or “Not yet,” then decide if you want to keep your foot in the door – but don’t get let her lead you on.

2) Suggest an impromptu meeting. 

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The Timing: 
In this scenario, you’ve only exchanged a couple brief messages each, and she doesn’t live super close-by. 

Normally, it would be too soon to suggest meeting.  But it turns out that you’ll be in her neighborhood this week. 

You’re confident you would have lots to talk about in person (this is absolutely crucial).

Go for it.  The key is to stick with a quick, casual date.  Since you’re suggesting meeting so soon after the start of messaging, she’s probably still unsure about you.  But if you suggest a quick date – coffee, ice cream, one beer, etc. – the efficiency of it will appeal to her. 

I’ve found that 30 minutes is enough time to decide if I find a guy attractive, enjoy talking to him, and sense he’s not a psycho.  But if the date doesn’t go well, I’ve barely wasted any time – like ripping off a band-aid!

How to Ask Her Out:
Send her a quick message that says something like: “Hey, it turns out I’ll be in your area on Friday, having dinner with a friend.  Any chance you’d be free for a quick drink after work?  If you’re not ready to meet yet, I understand.  But I’ve been enjoying our conversation so far, and thought I’d ask since I’ll be in your neighborhood that night.” 

If she’s not ready to meet, then you’ve covered your bases and can still ask again after some time has passed.  But your casual initiation just might seal the deal!

One of the best online dating meetings I’ve ever had was like this. 

We’d only exchanged a couple messages in two days, but he sent me a message like, “Hey, I’ll be driving by your town tomorrow!  Are you available around 4pm to meet for something quick?” 

We met for water ice, talked for half an hour, and then he continued on his way.  We dated for five months after that!

It was a great first date because our meeting was so casual.  I was more at ease than I’d usually be for a serious dinner date.  And because it was quick, it left me wanting more. 

Remember: meeting in person is the whole point of online dating. 

You’re asking her to meet you, not to do you a "favor."

When you are polite and reasonable, there is no harm in asking.  The worst she can say is “no” – and that’s good, too.  Better you know her answer now, not a week from now.  You can spend your time and energy on girls who want to meet you!

But chances are good that she’ll say “yes.”  You’re a great guy, and you’re making an effort to show that in your profile and your messages.  If she’s replying to your messages and keeping up her end of the conversation, then she does see meeting you in her future. 

So don’t be shy.  Just ask.  And get ready to plan your first date!

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