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?

30 Responses to “Dating Done Right: The Dreaded “Maybe””

  1. Leroy says:

    All personalities and perspectives are welcome in this blog, while personal attacks and name calling are not. It’s inevitable that there will be disagreements, but let’s handle it as mature adults with class to keep the dialog constructive and respectful. Please refer to “Blog Etiquette” on WhatsYourPrice blog for more details.

  2. Giselle says:

    Hm. Interesting. As a woman, when I say “maybe” (instead of a “no” because of non-interest or a scheduling conflict) it usually is because I’m unsure if he’s really that into me. When I say “maybe,” I wait to see if he insists, or offers alternate suggestions. Then when I feel special (not like his Plan B or C) I’ll say yes. :-)

    • Ted says:

      “because I’m unsure if he’s really that into me”
      If they guy asks you, then he is indeed into you. Are you looking for double clarification ?

      • Doug P. says:

        I agree. Most men don’t have scads of women to consider dating and we put a lot of pride on the line asking women out. No matter how polite a refusal is, it still makes us feel like a total loser. If we ask her out, we’re into her. If she says anything other than yes (Woman A in the example above was a yes, it was just a yes that had to be another time), it’s a clear no.

  3. Sophie says:

    I have used maybe before to try and let someone down nicely. But not people I have met already. I will be honest with a guy I have already been on a date with.

  4. bobby the k says:

    Wonderful post! Truly useful information. Dating is getting more and more fun using this site. Practice makes perfect.

  5. APB says:

    Had one of these. The instant she told me “not today” (trust me, it wasn’t going to be “today”) when I asked her out to a second dinner since one of my side job assignments asks for a sidekick and she didn’t come back with an alternative, it was next for her.

    Tell me, though, how do you solve this with a date who doesn’t really have any hobbies or interests that are apparent after the first date? You can’t, I guess. Her profile says she’s “tired of time wasters”, so…?

  6. chris says:

    Apb, shes just not that into you bro!

  7. nmchick says:

    Oh my my! I’ve used maybe before! My son got sick when I was supposed to go meet up with a guy. I told maybe another day because my son is sick I’m gonna go get him now! He told me ok I hope he gets better! I text him back and he never got back in touch. As a matter of fact, he blocked me on the website and I never heard a peep from him again ! Now I was being truthful with him as I am always truthful and even if he might not wanna hear it if there it’s no chemistry I will let that person know! Don’t misunderstand me it’s hard sometimes because you don’t want to hurt anyone’s feelings but I know I hate being led on! I was on my way to pick up my son at school when he msged me. I was hurt that he didn’t talk to me again after that because I liked him! Just wanted to share my story!

  8. Lore says:

    HA! If someone tell’s me if I can’t make it they will ask someone else, that’s it I’m done. Makes me think they are a player.

    • Anonymous says:

      Then your crazy or irrational. It’s not reasonable for you to expect someone to site around while you vacillate and can’t make a firm “yes” or “no” – thats also cowardice on your part…..

    • Anma says:

      I completely agree, and I believe most women would feel the same way. Saying, “I’ll ask someone else, then” just shows his true colors. A man with confidence who really liked a woman wouldn’t give up over a ‘maybe.’

    • Doug P. says:

      They’re definitely someone who can’t see that ‘maybe’ is a polite ‘no’.

  9. Sammy says:

    I have answered maybe, but always say I will get back to you within a certain time frame. I hate it when I am told maybe and don’t hear back for awhile. So, i make other plans and all of a sudden they guy is calling or texting saying, “Ok, I want to see you now.” Easy response, “Sorry, I don’t sit around, cross my fingers, praying that I will get called.” I would NEVER expect anyone to wait for my answer more then a few hours and would appreciate the same courtesy.

    Thanks for liatening to me vent. Obviously this was done recently. The guy threw a fit!! He though cuz he said maybe that night I should have waited around for him.

    • Gurtrude says:

      That’s because your a good dude. But if you want to get them salivating, you have to act like you’re busy and important but attainable at the same time.

  10. tony says:

    need company

  11. josh says:

    asked this girl out, but i called her a week before her birthday, and asked if she wants to go for lunch on saturday. she said she’s busy this weekend, with birthday plans, but said we’ll go out sometime next week. this was done over the phone, so i just told her to text or call me when she is free.

    either way it’s fine. a while ago she was interested in me, but i did not make my move at that time, since i did not know her at all at that point. one of my friends who was with us kept urging me for days after to do this, but i wasn’t feeling up to it.

    we went out again shortly there after, and my friend left me alone with her. at the end of the night i asked her for her number and she gave it to me.

    waiting to see how it turns out, but i’m kind of leaning towards a definite no now. only time will tell.

  12. Kichka says:

    I went out wit a girl three days ago and today I asked her can we have a dinner again. Unfortunately the closest date we can arrange was in two weeks. Then she said “may be”… I’ll tell you by the end of the day. Well I insisted for more straight answer for a little bit but she said its in two weeks. Wonder what to do? I don’t believe she’ll tell me by the end of the day :(

  13. Duff says:

    When the girl replies… “Oh that would be wonderful. I would love to because I miss you so much. The only thing is I have to pick up my son(or any other excuse). Right there, you MUST listen for sincerity in their voice. If their tone if voice is kinda whiney, then the answer is NO it will never happen because she “really” is not interested enough anymore to figure out to make it happen. Very easy to detect this.

  14. Taylor says:

    So idk if it was a good idea but this girl and i were talking on facebook and i said “hey do you want to go out to dinner or lunch? Set up a date or somethin” probably couldve been smoother than that but oh well anyways she said “Idk Taylor. Maybe? is that a sign of no interest?

  15. penguinapricot says:

    ‘Maybe’ is a test. How does the woman test if she really likes you ?.. she thinks about it, and she says ‘maybe’. If you are a Failure, you will try and push her for a ‘yes’. If you are a failure, you will ‘Next’ her and ignore her as if you don’t care thus proving that you DO care. If you are a Winner, you will say, ‘well let me know , and smile’. Then you will go off and do more important things until such time as she contacts you or doesn’t.

  16. Blunt Truth says:

    Look at it in this perspective. The main reason why guys do not as girls out on dates is because we do not ask. The reason why we do not ask is because 95% of the time “little girls” pull the maybe card. Real Woman give a yes or no answer.

    All girls that are younger than 30 and pull this maybe ridiculousness are in fact by definition little girls. It baffles me to no end when girls complain that they do not go on dates when they are the ones that pull out the maybe card instead of actually going out on dates and not flaking on or standing guys up.

    Do not give the excuses “well I just did not feel an automatic connection with him” excuse. Well did you even bother to put more than 10% effort in to finding out. If not stop complaining.

    Little girls want to be in a love story women want a relationship.

  17. Annon says:

    Ask a female friend and co worker out twice got no real response of certainty so left it a bit and she shown interest, her story her last relationship was tough as her ex still works at my workplace and when they split he bashed her reputation bad! She likes me but is unsure as to put her reputation in my hands, I finally got her number asked her out several days ago but she wasn’t happy with location so I rearranged it and she is busy with the day although she did say before that fridays are not great as she is busy, sadly all I have is Friday as I’m busy with lads Saturday, Sunday she works nights till thurs so I just asked well what’s best for you? So if she decides to say no really got time at the moment then I’ll come clean and tell her I just wanted to go as friends but testing to see if you are gf material! I have a soft spot for her but I can’t exactly tell her I’ve also collected several other numbers from really hot women like herself lol the hottest of them seems really into me and thats great but it’s hard to try and date a female friend who also knows you wanna sleep with her lol and remain friends. I’m a straight talking guy I go out of my way to get what I want, I let her know how sexy she is and how much I like her but at the same time I let her know how much I respect and care for her. Basically guys the best way is to handle rejection with a smile and remain friends, move on but keep the chatter chatter going with them. It gives you confidence and gives the women the attention they want and boosts their confidence. How can that be a bad thing? Any guy that falls for a woman and can’t live without her before he has got to know her needs to meet women. Any woman that won’t give you time of day over a text should be forgotten as those women are not friend material either!!!!

  18. Poin Dexter says:

    About 10 minutes prior to sixteen hundred Zulu.

  19. Tim says:

    I like this because I hate waiting on people. As a 23 year old man I think I get a lot of maybes because my female colleagues are very career oriented. Giving them a deadline to respond is both casual and stops me from having to wait on them, which is super annoying. I didn’t say “can invite someone else” I said “so I can make alternate plans” since that seemed a little more casual. Who wants to hook up with someone who’s already offended you said you might be busy?

  20. Diana Rose says:

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