How to Ask a Girl Out Online

So just recently I started following @SingleGirlsAnonymous on Twitter, reading their tweets and blog posts and quite frankly I just loved what they had to say! So much so in fact that I decided to reach out to them to see if they were interested in giving us an insight into what women think about this online dating “game”. They suggested the topic of how to ask a girl out online and I absolutely loved the result!
Today’s post is written by the three girls that make up the group, Claire, Leslie & Addison (lovely name btw :)). They are all in their thirties and blog about their dating experiences in hilarious fashion. You can read their blog here.

Now, onto the girls’ post, everything from here on is written by them.

How to Ask a Girl Out Online

Guys, it’s time for some tough love. We hate to break it to you, but you’ve got a little bit lazy when it comes to this whole online dating game. Introducing yourself virtually with “waz up?” or “how u?”, passively asking us out, then making us plan the first date and/or pick up the bill. YIKES!

If you’re on the hunt for Mrs. Right this is not likely the way to attract her. If all you want is to be seen in public with a hot girl from time to time this may be working for you…Carry on. Otherwise, read on.

Look, it’s not your fault. We get it—times are changing, everything is fast-paced, superficial, and sometimes the whole thing feels like one big joke. But at the end of the day what do you want out of all of this? Are you looking for an actual committed relationship, someone to go eat guacamole with, or just a hookup (hey, no judgment here)? In any case, you’ve got to put in a little effort to move things from the virtual to the real world successfully.
Sure, the passive approach may work some of the time, but it doesn’t exactly lay the foundation for romance, and definitely not for a hot hookup. So step up, grow a pair, and put yourself out there. It’s not so hard, and what do you really have to lose? This person is essentially a stranger until you make the move to meet in public. If she doesn’t reciprocate, will your ego really be badly hurt by a total stranger who has no idea how awesome you are IRL.

If you have been messaging back and forth with someone for a little while and she seems interested in you (and you already know she thinks you are reasonably attractive), trust us she will more than likely be open to meeting up in person. The quickest way to kill the chance for romance is with a lame date request. If your intention is to take this girl out and let her know that you are a man worthy of her time, then please DO NOT use any versions of the following statements:

  • “I’m not doing anything Saturday, maybe we can hang out?
  • “If you want to get together sometime, just let me know.”
  • “Drinks?”
  • “I might be out Friday night, maybe if you are too we could “run into each other.”
  • “Let me know if you ever want to meet up, or if you want to keep talking that’s cool too. Or let me know if you want to text instead. Whatever.”
  • “Here’s my number if you want to chat.”

At first glance these may seem okay, you are, after all, letting her know you are interested (kinda). But again you can do better. (Please do better, we are begging you). Instead of dipping a tentative toe in the water, jump right in and ask her out like a man!

Gentleman, repeat after us:

  • “I would love to get to know you better. Would you be interested in grabbing a drink with me sometime after work this week?”
  • “It’s been fun talking to you, let’s do it in person sometime soon. Do you want to check out that new Mexican restaurant with me later this week?”
  • “It sounds like we have a lot in common. Can I take you out to dinner Friday?”
  • “It has been great hearing about your interest in…I would love to find out more over drinks.  Would Thursday be a good time for you?”
  • “I’m free on Tuesday or Wednesday after work, would you be available to meet for dinner?”
  • “May I have your phone number so that I can continue to get to know you and schedule a date this week.”

Boom, simple. Show her that you are clearly interested and available by being direct. And when she says yes (because trust us she will) follow up with her and arrange the date. This means settling on a time you are both free, deciding on where you will meet, and locking down the rest of the details as soon as you can.

And while we are at it, let’s discuss the fact that you have a limited window to complete this in.  If you are messaging back and forth with her and decide that you are somewhat interested in her, DO NOT continue sending her messages for days on end. She has friends she can exchange pointless texts with all day. She does not need a pen pal. Especially a stranger pen pal. If you are not going to ask to meet her IRL within a few days, do her a favor and leave her alone.

And that gentlemen, is how it’s done!  No need to thank us when the dates start rolling in, just pass this simple message along to your boys! Or send wine…we love wine!

Need advice for what to do now that you’re actively dating? Want to let us know if our advice worked? We would love to hear from you — reach us at

I’d like to say a massive thank you to Claire, Leslie, and Addison again. It’s great to finally have an insight on how to ask a girl out online!

Happy dating,

The Frequent Dater

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