3 Simple Steps to Asking Someone Out

I had never really been in the dating “game.”

I had always been pretty comfortable around the ladies, don’t get me wrong, but found myself in *the friend zone* far too often than I’d prefer to admit. (Narrator: it was all the time). In other words, I ran into trouble somewhere between starting a conversation and actually asking a woman out on a date.

And then I had a conversation with Mike, my first roommate out of college. Mike was a few years older (and wiser) than me, and his insights changed everything. He taught me his simple formula for asking a woman out on a date, a formula with which he said he had excellent — if not infallible — success.

Fellas, let me present The Three Step Plan for Asking a Woman Out on a Date^TM.

1. Start a conversation.

Now, I still feel fairly comfortable starting conversations with women, but this is still many times easier said than done. Especially when it’s a woman who seems to be — how to put it — out of my league? But it’s amazing to me that if I just lead with something I find genuinely interesting, all of a sudden the impossible hurdle of talking to a beautiful woman didn’t turn out to be so bad after all.

Of course, some won’t be interested in entertaining your conversation-starter. In that case, you were probably too forward or otherwise too weird, it was too late at night (or too shady of a bar), or she just simply wasn’t interested. It might even have been some combination of all of the above. Sometimes it’s impossible to know, of course, so all the more reason to avoid those first two pitfalls as much as possible.

And even if it turns out she simply wasn’t open to a conversation with you, the important thing is that you tried. It’s like what Michael Scott says about what Wayne Gretzky says: You miss 100% of the shots you don’t take.

So try! Give it a shot. Start a conversation.

2. Continue the conversation.

Then, after you’ve had a nice interaction, say something like, “I’m really enjoying this. We should continue this conversation sometime over coffee/lunch/happy hour.”

As I mentioned earlier, my biggest hang-up was the problem of moving from good conversations with women to an actual date. Perhaps I had built up in my mind that it was going to happen magically without any sort of effort, or much more frighteningly, that it had to be some elaborate invitation: “My dear lady, you really are a rose among the thorns. Please, would you accept my overtures and allow me to take you out on a proper date?”

When Mike first explained to me his *system*, he broke it down to me in a very straightforward, accessible manner. Whether you have already fallen madly in love with this woman or not, chances are she hasn’t fallen madly in love with you. The important part is that you’re interested in getting to know her better. Express that in a simple, non-threatening way.

Think about it. If you were to ask something like, “Would you like to discern our predestined future together over a romantic candlelight dinner?” that would probably be an easy “no.” But if you say, “Would you like to continue this conversation sometime?” you’ll find a much higher probability of success.

This obviously is more effective if you’re discussing something substantial and thought-provoking — like why the Vikings decided to pay Kirk Cousins $84 million guaranteed instead of bringing Case Keenum back — rather than something banal, like the weather. Or, perhaps more to the point, you’ll have a better shot at a follow-up date if she’s actually showing some sort of interest on her end and you’re developing some sort of rapport.

But if you’re anything like me, you’ll discover that some women can be hard to read. Sometimes you seem to click from the start and she seems to be giving you signs to ask her out, and then when you actually do, she says she can’t because she has to go wash her hair or something. Or it might seem like she can hardly stand your existence, and then she’s thrilled to accept your invitation to a date. In my experience, you never really know until you ask. So ask!

3. Ask to be in touch.

Then, if she says “yes,” follow up with, “Cool. How should I get a hold of you?”

To a man with no clue, like me, the prospect of asking a woman for her number was the ultimate bugaboo. The fear of rejection was paralyzing enough to prevent me from ever asking, even if I came upon a decent opportunity to do so.

In hindsight, the fear likely had something to do with the fact that it would seem unnatural and overly forward, maybe even desperate. But in the context of a pleasant conversation, and a mutual desire to continue the conversation — which leads to the necessity of a way to follow up with one another — all of a sudden the question no longer seemed the least bit overly abrupt or unnatural.

Ultimately, there’s no formula necessary for asking a woman out on a date. There certainly is no fail-proof method. Which isn’t the point, anyway. Besides, if a woman feels tricked into a date — much less pressured or coerced — that’s no way to start a relationship, anyway.

For me at least, my roommate’s method served to demystify the whole process and help me wrap my mind around it in a way that made me much more comfortable and confident. And the more that I talk to women — my sister, friends, and potential dates alike — the more I realize that women often deal with the same sorts of frustration and trepidation as I and my fellow men face in the dating “game.” And — news flash — some wish more men would just be bold enough to speak plainly and just ask them out.

So, guys: What are you waiting for?