Advice and Insights for Modern Daters

Waiting for a Sign?

Why do some people take forever to ask for a number or plan a meet-up? Alli and Jen give advice as to what’s up with this frustrating dating app situation.

Q. Why do some guys take so long to ask for my number or to meet in person?  Are they waiting for some sort of sign from me?  I would much rather talk in person than through the app for so long.

Jillian, 28, New York, NY

A. I agree! Texting is the worst. The dating world is obsessed with it, which makes no sense, because any single person on the apps can tell you that you know pretty instantly after meeting IRL whether there’s any potential. You really can’t tell anything from words on a screen. 

That said, there are a few reasons why someone might wait so long to bite the bullet and ask if you want to meet up:

  • He’s been scarred before; e.g., he’s met up with multiple girls who have turned out to be total lunatics. You know how you’ve been on a million bad dates? So has he. The result is that he’s being extra careful.
  • He’s waiting for a sign from you, which is totally lame, because you matched and are bothering to text. If he needs more of a sign than that…well, it’s up to you if you’re into shy, nervous dudes.
  • He’s a classic d-bag who likes to match with and chat up girls as an ego boost, but doesn’t actually want to meet. (No joke, I know guys who do this, but they’re in the minority. Let’s all believe in a better world and always go in assuming that Option 3 is not the case.)

My advice is to text something like: “So, here’s my number.” Or: “Are we gonna meet IRL or what?”

I do personally love a little chivalry, but the fact is that a first online date isn’t even a date; it’s a meet-n-greet. You’re seeing if the other person is real, and if he looks like his profile — basically, if there’s any chemistry at all. So it’s really not going out on much of a limb to ask a guy that you matched with, who is texting you, if he wants to meet in real life. If you’re old-fashioned, let him be the one who asks you out after the meet-n-greet, because that’s the actual first date.

The moral of the story? Just ask when you’re meeting up. If he doesn’t bite on that, BAI! You’ve got better things to do than text.

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Allison Goldberg & Jen Jamula are the creators of two live comedy shows — Blogologues and How To Break Up By Text — both of which look way too closely at online dating, and now they’re here to share with you all the things they can’t unsee. Their work has been featured on Good Morning America, in WIRED, Forbes, VICE and more, and at one point Time Out NY ranked them among the top ten funniest women in NYC — but they were ranked as one person. Send questions to Alli and Jen at


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