How to Ask For a First Date

Asking someone out tends to be a little nerve-wracking. While a few lucky people are blessed with supreme levels of confidence (more power to them), most of us tend to be a little more hesitant.

One thing is for sure though — asking people out online is a lot easier than it is in “real life”. It’s far less about courage, and more about simply having a process. Once you understand how to go about getting dates online, the nervousness can all but disappear.

first date

Besides, when it comes to asking for a first date, it is far less about how you ask, and far more about the circumstances. First things first — you’re going to need to contact some prospective matches in order to ask them out. With that in mind, you may want to read my guide on sending the first message.

Personally, I like to contact a lot of girls — even if I’m not totally convinced that they’re a good match. The reasoning behind this is because you can be surprised how someone’s profile doesn’t really reflect their true character — it’s always worth a punt.

However, that works both ways. In the same way that a thoroughly uninspiring profile can be written by a thoroughly interesting person, you can find that a profile seemingly does not gel with a person’s character when you email them.

So don’t think about contacting a match as the first step towards asking them out — instead consider it a way of discovering whether or not he or she feels “right” for you. Once a first message becomes less about achieving daunting things, and more about testing the waters, it seems far less imposing.

I advocate asking someone out sooner rather than later — typically within 2-4 messages, spread over say 3-7 days. This is long enough to decide if you think someone is worth a first date, but not too long that you are pouring time and effort into a worthless cause, if that person isn’t interested in a date. It’s also not so short as to come across as overeager.

Therefore, you only have a handful of messages to build up a good rapport with your prospective match. As I said at the start of this article, we are looking to set up positive circumstances under which it doesn’t really matter (within reason) how you ask your match out.

So get as much value out of those messages as possible. That doesn’t mean that you should write essays — just concentrate on asking interesting and fun questions, and giving interesting and fun answers. Strike up a little bit of dynamism. If that spark isn’t there, perhaps that person isn’t right for you anyway (although that is not always the case).

Once you have exchanged messages, the time comes when you need to ask the all-important question. My approach to this has always been completely casual, and not particularly well thought out. And yet, it seems to work for me. More often than not, my proposition goes along the lines of: Would you like to meet up for a drink sometime?

Nothing particularly exciting I’m afraid — but that’s the whole point. Your question doesn’t need to be unique or awe-inspiring.

Getting “rejected” in the world of online dating should be a non-event, because you can never be sure why you got rejected. Your match might only be looking for online pen pals. They might not actually be interested in going on dates. They may have stopped using the site. Who knows? The point is, you don’t, so don’t bother fretting over it.

So just go for it — ask them out for a drink. It needn’t be anything more complicated than that. If you follow my tips above and in other articles on this site, you will be getting positive answers in no time at all.