Getting that date: Five suggestions

So, a while back I wrote a series of posts on the subject of dating which turned out to be rather popular. People clearly love to read and talk about relationships! At the end of the series, several of my friends asked me if I would be writing more entries, but I told them that I’d already said everything I had to share on the subject.

Well…it turns out that I was wrong, because here I am, a year later, writing another post on the subject of dating. A while back, I had a friend of mine message me and say “I wanna ask someone out. Any ideas for a date and how should I ask her out?” Clearly, word had got around that I now have a beautiful girlfriend and this qualifies me to answer a question of this magnitude!

Seriously though, as I wrote in an earlier article, Catholic guys are generally pretty terrible at asking girls out, so I think it’s worth publishing the answer I gave my friend. Not everyone will agree with what I have to say, but that’s fine, please leave a message in the comment box.

Now, I have not always followed the suggestions I am about to give below, but I wish I had. My advice represents the solution to some of the different kinds of mistakes I’ve made in the past… 🙂

1. Do it in person
To ask someone out via text is really lame. Doing it on the phone is pretty weak. In my opinion, you should do it face-to-face. Is this scarier? Yes. Will it be kind of awkward if she says no? Absolutely. However, you’re a man not a mouse! So put down that cheese and go do it in person!

Now, I should note that there are some occasions when it’s actually not possible to do it in person. To pick a purely hypothetical example, you might decide to romantically pursue a friend who lives in another state, Washington perhaps. To avoid asking her out on the phone, you might visit her and ask her out in person while you’re there. However, there’s always the danger that in the intervening time that she’ll start dating someone else. So, if you want to lock down that date before you get on a plane, I’d suggest asking her out via video chat (Facetime, Skype etc). Again, this is purely a hypothetical example… 😉

2. Be direct and confident
No mumbling. Don’t speak too quickly. Ask her out simply, clearly and confidently.

3. Use the “D” word
Use the word “date” when you ask her out. I know it’s tempting to try and organize a “stealth date” where she doesn’t actually realize that it’s a date. Although this might seem like the lower risk option, I wouldn’t recommend it. If it’s a date…then call it a date! In my book, it doesn’t count as a date until you use that word. Not only that, otherwise spending time together can too easily be misconstrued as just two friends just hanging out. Using the “d” word gets rid of ambiguity and you both know where you stand, which is ultimately far better than a confusing limbo alternative.

But what about if you’ve just met someone you piques your interest, but whom you’d like to get to know better before asking out on a date? Well, in this case, I’d suggest hosting an event with a small group of friends (4-5). This will allow the two of you to spend some more time together, to get a measure of each other’s characters and get to know one another as friends before deciding whether you would like to take the relationship further.

4. Have a time in mind
When you ask her out, suggest a day and an approximate time. Have a good idea of what your schedule looks like so you know what alternative days and times to suggest.

5. Have an activity in mind
Don’t be caught off-guard if she asks you what you were planning for the date. It’s a good idea to have a few ideas in mind. Here are a few good questions to ask yourself when planning the date:

(a) Will she enjoy it?
Build the date around something you think she’ll enjoy. If she enjoys herself she’ll be more relaxed and more likely to agree to another date!

(b) Will it present you in a favourable light?
You want her to like you! Therefore organize a date which will allow you to demonstrate to her some of your best characteristics. If, for example, you’re a sore loser, it’s probably a good idea not to arrange a highly competitive date!

While showing interest in your lady’s hobbies is a good thing, I would personally suggest being a little wary of suggesting a date which is focussed around one of her interests where you’re likely to flounder. For example, if the girl in question is an experienced salsa dancer and you’ve never done it before, I would caution against going to a salsa club on your first date. While your willingness to organize a date around her interests is commendable, you run the risk of souring the evening by frustrating her with your two left feet. The date might go well, but personally I wouldn’t risk it. Instead, I would recommend postponing this kind of outing until a later date, and in the meantime get some salsa lessons without her. When you do finally go with her to that salsa club, you will not only be a less frustrating partner, she’ll see how much you care for her by the effort you made to ensure that she had a good night out.

(c) Will it nurture the friendship?
The goal of the date is to get to know one another better. This is why I think going to a movie on a first date is a bit “meh”, since you’ll be spending the first couple of hours of the date in complete silence! If you’re thinking about going this route, check that she actually likes watching movies and make sure you have time together afterwards to talk. Oh, and as a word to the wise, I’d also suggest picking a good movie, making sure that you read the synopsis beforehand! Oh, I have disaster stories… 🙁

So there you go, those are my suggestions. I’m sure other guys have different advice, but if you were to ask me, this is what I would say.