A Realistic Approach to Starting a Conversation with Someone New

How many times have you read the following tips for striking up a conversation with your new crush?

No. 1: Be confident
No. 2: Be positive
No. 3: Be engaging
No. 4: Show interest

This seems like common sense, so why is it that these words carry little weight in a real life situation? You can read this list a dozen times and it would not be surprising if they never propelled you to action. So what’s gone wrong here?

The first problem with this list is that it confuses what is ideally the case and what is really the case. Although tip No. 1 reads, “Be confident”, what it’s really saying is, “Ideally, be confident.” For some, confidence is not something that can just be switched on in the face of a daunting scenario.

The second problem is that it assumes awareness of these tips is enough, as though the audience reads the tips then says, “Ooooh, so I should be positive. Hmm, I never considered that approach.” This audience would benefit from this list, but it’s doubtful the ideas are novel to anyone.

And the last problem with this list is that, in some sense, it doesn’t work. If this were the tried and true way, it would only need to be said once, and slowly but surely, the lines of communication between interested singles across the world would begin to open up . . . and we’d all live happily ever after. But the truth is, something is lacking here and just repeating these platitudes won’t get the shy, quiet, or anxious to take a single step toward his or her infatuation.

So how should we approach this dilemma? What can realistically help you, the reader, start a conversation with someone new? First, instead of speaking generically to a generic audience, there needs to be a certain level of identifying and intimacy between the advisor and advised. Although it is simply not possible to take into account every single person’s situation, it should not be assumed that one answer fits all. Rather, let us start from a deep and personal place; one in which we sometimes have to admit to ourselves that we aren’t ready to employ tips 1-4 above. If you are one of the fortunate enough to have a handle on one, or all, of the tactics listed above then you needn’t start with the rest of us. However, if you are part of a majority who fear showing interest, don’t have the knack for being engaging, and have trouble demonstrating confidence, then be aware that this is probably the place where your crush is starting too.

This observation can prove extremely useful when sizing someone up. If your crush is single as well, he or she more than likely faces your own struggles too. Very few are completely comfortable in such a setting as finding the right words to say in a short window of time. This is analogous to the advice you receive when giving a speech: imagine the audience in their underwear. Sometimes you’re the speaker, sometimes you’re the listener, but at some point, we’re all caught standing in just our underwear. And somehow, this takes some of the edge off. This is part of the realization that your crush is probably just as vulnerable, nervous, and scared as you are.

Do not distance yourself from that guy or girl you’ve had your eye on by assuming that he or she is above feeling uncomfortable or awkward in an undeniably uncomfortable and awkward situation. Identify with that person by putting yourself on the same playing field. It is unreasonable to grant your crush the advantage of mastering tips 1-4 above when you don’t know him or her.

So, the insight is simple enough: your crush is more than likely just like you. And our realistic expectation of walking over and saying Hi is that it will be awkward and uncomfortable, but for the both of you. This article has no foolproof one-liners, mental exercises, or cliches that may or may not work. The fruits of our labor are modest–we are similar in our hopes and fears; no matter what we say when we start a conversation with someone new, we will create a new and uncomfortable environment; and no matter how much you are mastering or lacking of the tips mentioned above, there is no one way to break the ice with that cute guy or hot girl. All that I can expect is that you are like me and whether I walk up to you, or you me, to start a conversation, we’ll stumble our way through it together.