When Should I Ask For A Date Online

The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch – or several.
The Question
Hi Dating Nerd,
I’ve been chatting with this girl online she’s really exciting. She gets my jokes (girls never get my jokes) and she makes me laugh too. It’s been about a week since our first convo, and we’ve spoken 3 or 4 4 times since then. I know the move now is to ask her out, but I’m kind of a nervous wreck about it. I’m worried she’ll say she doesn’t see me that way or just ghost me, so I keep avoiding it. Is there, like, a rule about how long you should wait before asking someone you met online out on a date? Even a made-up one that could convince me to pull the trigger instead of just avoiding it every time we talk like I’ve been doing?
– Nervous Wreck
The Answer
Hi Nervous Wreck,
When should you ask your crush out? As soon as possible. That’s the general idea. Get that number, get off the Internet, get into a nice wine bar, close that deal. Swallow your stupid fear and just do it. More specifically: Do it as soon as you can without seeming creepy. Don’t worry – despite being one of the central problems that people face when they use online dating sites , this actually isn’t that hard.
Ultimately, the sooner you’re off her phone and in her real life, the better. It is because, if she’s a reasonably attractive person, her online dating profile is absolutely saturated with dudes, all of whom are relentlessly giving her compliments about how her hair flows like a majestic unicorn or whatever. Now, they obviously aren’t as charming or good-looking as you are, but she won’t be sure of that until you’re actually hanging out in real life. You don’t want to jostle for her Internet attention span, you would like to cultivate a real connection.
Also, boldly asking somebody out displays real confidence, whereas chatting for weeks without making a move suggests that you’re a wimpy little lily-livered scaredy-cat who can’t take a risk on anything. Which is terribly unattractive. You’ve got to show her you’ve got a pair of testicles. (Metaphorically. Keep your pants on. Only send pics of your junk if they’re clearly and explicitly solicited.)
The only trick is the without seeming creepy” part. If you ask her too soon, you risk coming off as desperate – like you can’t possibly go another hour without the possibility of touching a woman – or like you can’t devote any effort to woo her. That is also unattractive as hell, in different ways. In the event that you come off like you’re starved for attention, she’ll wonder why. And you can find hardly any good answers compared to that question.
So it is a balance. Unfortunately I cannot give you a precise number here – while I know everything about dating and my advice is definitely flawless, I’m not just a psychic. I can’t say, You should ask her out when she’s typed exactly 972 characters and three emojis, and then you will get laid immediately.” You need to use your big brain here and pay attention.
Basically, you have to look for signs that she’s into you That she regards you more than just another guy. And then you have to ask her out as soon as you have one of those signs of interest. Fortunately, there are a lot of signs, and they’re not particularly hard to see.
The most telling sign is that she’s displaying vulnerability – that she’s telling you actually important stuff about her life. Maybe she’s confiding in you that she’s worried she’ll lose her job at the bank because she mislaid several million dollars in gold bars. Or that eating rare steak reminds her of her beautiful childhood years, back when she lived on a ranch in Alaska. Or that she doesn’t know what the hell she wants to do with her life, and she’s worried about becoming her mom.
Unless she’s a massive oversharer, she’s not giving every dude these confessions. Telling you this stuff means that she trusts you. And if she trusts you enough to give you her secrets, she probably trusts you enough to give you a lot more.
Another good one is if she laughs a lot. Funny is absolutely invaluable. If you get a you’re so funny” from someone on an online dating site or app, what that more often than not means is ask me out immediately, you’re so refreshing in comparison to all of the humorless idiots who constantly hit on me.” You’ve transcended the role of random dude from OKCupid and potential stalker.” Congratulations.
There’s more. Do it now if it looks like you’re sharing a whole lot in common, like if you are both waxing poetic about all of your favorite characters who got brutally stabbed on Game of Thrones. Common ground means a whole lot in internet dating – it is a big relief to perform into somebody who actually gets what’s happening in your brain, instead of just what may be going on in your pants. Incidentally, this means that you need to really strive to find out what she’s thinking about, and at least execute a very convincing impression of someone who’s thinking about that.
Last one. If she’s providing you compliments, that’s an exceptionally good sign. Whereas men hand out compliments like candy canes at Christmas, women don’t hand out compliments lightly, since they understand that dudes, let’s admit it, are suckers for flattery. If she says your life sounds awesome, or that you have a hot bod, usually do not hesitate, ask immediately. She’s providing you the all systems go.
So how can you do it? Well, just keep it simple. Avoid being all flowery, don’t overthink it. Back my internet dating days – that have been pretty successful – I preferred putting it as a statement rather than question, like Let’s embark on a date. Are you currently free Thursday?” This comes off as assertive and no-B.S., but it addittionally gives her an out if she really wants to take it, so it is not creepy. Understand that if she says she’s busy but doesn’t let you know when she’s not busy – if she doesn’t offer another date – you are out of luck, at the very least for now. Sorry.
My last little bit of advice? You should be realistic if you are reading these signs. If you are lonely, you can belong to a trap where you imagine any woman who doesn’t immediately chase you away with a baseball bat is thinking about you. Be mindful that you have not necessarily piqued her interest because she responds to your messages. Take time to lay some charm down before you make your move. Then make it.

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