Dating Done Right: The Dreaded “Maybe”
  • Posted Oct 22, 2012
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So you’ve met a girl last weekend who really piqued your interest. She was attractive, intelligent, and the conversation flowed naturally. To top it all off, you got her number—a personal success in any man’s book.

It’s now Monday, three days later, and you’re racking your brain for ways to creatively ask her out. As luck would have it, your roommate offers cheap tickets to a local show he can’t attend. You obviously jump at the opportunity with one person in mind: her.

You buy the tickets and present the offer. But to your dismay, you get a response that poses a problem for many singles: the dreaded “maybe.”

Does “maybe” mean she’s busy, or not that interested?

For those of you who are not familiar with the dreaded “maybe,” it translates into two things in the online dating world:

1.) I’m really not that interested right now, but if there is nothing else to do this weekend…
2.) My answer is “no,” but I feel bad telling you directly.

While some may disagree with this notion, citing previous dates where maybes turned into “yes,” let me ask you this one question: What have you encountered more with a “maybe”? An eventual yes, or an eventual no?

Ask any woman— if they really want to date you, then they will the find time. At the very least, they will offer up an alternative solution. This in itself separates those who are genuinely interested (daters), from those who aren’t (users).

For example:

Woman A – “I’m really sorry, I can’t see the show on Saturday. I have to work late this weekend. Is there any way we can have coffee or lunch on Sunday?”
Woman B – “Wow, that’s great! Maybe, I’ll have to check. I had already made plans with friends.”

Which woman truly has your best interest in mind? Woman A delivers the bad news directly and offers to amend the situation. Woman B expresses enthusiasm, yet her response is rather vague and unclear.

If you chose Woman A, then kudos to your dating intuition! Woman B leaves you in what I like to call “dating purgatory.” In other words, you don’t know whether to bank on her at the risk getting ditched. And you don’t know whether to ask another girl at the risk of losing her approval. Sucks, doesn’t it? We’ve all been in this situation.

But what if I told you that this can be completely avoided?

Next time she presents you with a dreaded “maybe,” do the following in order:
1.) Tell her that you look forward to the date, but will settle for asking someone else if she cannot attend. Showing that you have other options (competition) will increase the value and desire of this opportunity.
2.) Give her a deadline for her answer. Obviously, don’t use the word “deadline” (you’re dating, not writing a newspaper). This will add a sense of urgency to the situation and provide ample time for a Plan B, if needed.

By being honest and staying in control of the situation, you will not only better your chances of turning a maybe into a yes, but you will always have other options. After all, the last thing you want is two tickets and no date.

Have you ever experienced the dreaded “maybe?” How have you dealt with it in the past?

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