Internet Dating for Rookies #8 The First Date “ask-out”

Asking someone out online is an art not a science. There are obviously things you can do to boost your chances of a “yeah I’d be happy to meet up” reply but it’s never a sure thing. In this article I’ll cover the key things to ensure when asking someone to meet up in person for a first date.

Timing is everything
 So the first key part in asking someone out on a first date is timing. You should already be in a position where you’ve messaged this person a few times. I’d recommend asking someone to meet up for a date after the 5th or 6th message. My rationale is as follows. The first couple of messages are simply intro messages, the next couple are about how your week has been going and the next couple are likely to include a little more substance (perhaps they confide something that a lot of people wouldn’t know about them). It is at this point that you should be asking them out. Leave it too long and you’ll end up as pen pals who write long “letters” to each other but couldn’t possibly meet up because it’d be too much of a big deal. Conversely if you ask them out too soon it’ll seem to forced as you’ve not had sufficient time to form a suitable connection. So, just as with comedy, when asking someone out, timing is everything.
How do you ask?
You’re ready to send that all important message, but how do you go about it? Well I’ve got a sure-fire winning formula for you to use (I’m too good to you guys!). The first thing to say is that the “ask out” message should not be a message in its own right. You don’t want them to receive a message from you out of the blue / cold which simply says “would you like to meet me?” (Also that wording is pretty poor btw). So your “asking out” request should actually be at the end of your next message – they’ll have read your engaging message and they’ll be a nice surprise waiting for them near the bottom. The wording I’d recommend is as follows…
“You seem like someone I’d like to get to know better. Did you fancy a coffee sometime?”
That’s it. The secret to asking someone out is to keep the request as casual as possible but ensure you are being direct and clear that you are asking them out.  You’re not trying to heap loads of pressure on them. Saying something like “I can really see myself falling for you, would you like to meet me face to face for a first date?” is likely to ruin your chances. So stay breezy and go for it.
Gauging the response
The part after the “ask out” message can be difficult. You’ll no doubt spend time thinking anxiously about their response but you must ensure you’re not too invested already (which is another reason you shouldn’t let the messaging extend past five or six) and if you’re following my teachings this wouldn’t be the only iron in the fire so to speak. When the reply comes, again like most things relating to dating, it’ll fall in one of only a few categories.
1. “Yeah sounds good, I’m free this Sunday if you are?”
2. “I’m probably not going to have much free time in the next few weeks because <insert bullshit reason here>”
3. No reply
If it’s a #1 well done, you’ve got yourself a date! Obviously you’ll arrange a suitable time and place (I’d recommend a local coffee place, at 3pm Sunday).
If it’s #2 two that’s also fine, they’re not interested in meeting you but feel bad about saying that so they’re making excuses. Either way, I’d suggest you drop #2 a quick reply back saying “no worries, catch up with you later”. It lets them know you’ve got the message (figuratively) and rounds off the message exchange appropriately. No hard feelings eh…? They may well reply back to that with another load of excuses but you needn’t waste any more time responding. Once difficult, always difficult is the rule here with #2.
Unfortunately, there will those who simply don’t respond. Perhaps you were too hasty in asking them out or they were only on the dating site to pass the time and aren’t that serious about finding love. Either way, there’s no need to pursue them any further and certainly don’t think about sending them a follow up message. It was only a quick coffee meet-up you were suggesting after all – not for them to be your organ donor!
And there you have it. We’ve reached the end of this series relating to The Rookies Guide to Internet Dating. I hope you’ve enjoyed it. Look out for the next in the series, The Rookies Guide to Speed Dating.
Happy Dating all! 
David Cohen – The Dating Guru

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