How hard must a man work to get a date with you?

Some women play hard to get on purpose. Some just end up being hard to get because of circumstances.

What if a man asked you out 28 times before you said yes? He’s not a creep, nor a stalker, but someone who’s genuinely interested in you. He’s kinda cute, nice and pleasant, but you have a boyfriend who you’re not getting along well with. And this guy sent you a dozen roses before you finally accept coffee with him.

ShawnaI was having dinner with my friend Shawna Schuh and her charming, delightful husband Don Potesta. We were talking about how they met and the above story emerged. But the story gets even better.

Over coffee, he revealed three things which were deal breakers for her. After a short while, she was done and said, “I’m leaving. It was great to meet you. Good luck.” To which he responded, “No problem. I only date women for two weeks anyway.”

This piqued Shawna’s highly competitive nature. She said she would accept his dinner invitation because she was so sure he would be unable to resist dating her for longer then 2 weeks. Much longer. And sure enough, she was right. They’ve been married 19 years.

And Don continued his wooing her. Every week he sent her a dozen roses to work — for sixteen weeks. And every time he showed up to take her out he brought a single red rose. This man knew what he wanted and how to win her.

Many of us would have blown off a guy who was so persistent. Maybe we would think he was arrogant, clueless, or desperate. Or the aforementioned creepy. But Shawna knew he wasn’t any of these, and even with three apparent deal breakers she saw his clear interest in her and she gave him a chance. And is she ever glad she did.

How hard do you make it for a guy to date you? It is hard to determine where you should be on the continuum of being too eager to say yes and being too hard to get. While men typically like a challenge, most would give up after being told no 28 times. Where do you put yourself on this continuum?

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6 responses to “How hard must a man work to get a date with you?”

  1. Bookyone Avatar

    Hi DG,

    This is a great story, it’s nice to know there are still some happy endings out there. I guess I’d be considered easy; (not in the sexual sense, but in the dating sense); if a guy wants a date with me, all he has to do is ASK. Unfortunately, most guys never do, they stare at me because of my bad skin, but they never speak to me. I guess bad skin is a deal breaker for them, which may not be such a bad thing altogether, as this weeds out the shallow, superficial types right off the bat, before they waste my time and energy.

    I’ve heard of women (and men) playing hard to get, but I wouldn’t know how to do that, it’s not in my nature. I am the original WYSIWYG gal from the word go, no game playing here.

    Best wishes from bookyone 🙂

  2. Marina Avatar

    I’ve never played the hard to get game. The reason being is over the years male friends have told me how scary it is to ask a woman out in the first place because they have a real fear of rejection! Because of that fear, some of my freinds tell me that if a woman plays hard to get they immediately move on to someone else.

    Likewise, I have inadvertently turned men away who have asked me out, and I had already made plans for the day they wanted to take me out. I would thank them, regret that I was not available that particular day, and let them know I would love to get together at another time. For whatever reason, they wouldn’t call back, and I would feel bad about it.

    I’m not a game player. I believe in being honest. Therefore I don’t play hard to get. I don’t want to take the chance of turning off someone who may be a really good match.

  3. Fred G Avatar
    Fred G

    Just out of curiosity – I am dying to know what the 3 deal breakers were in the case cited above.

    Deal breakers mean well – to a point. Some are valuable ( hitting other partner – should be deal breaker for most). Some are wish fulfillment ( financial situations, height, relationship romatic style, allowed sexual activities).

    My friend had a few deal breakers. “She should be earning within 20% of him – she should be within 5″ of him (he was 6’2″), she should be living on her own”.

    I was his best man at their wedding – all three deal breakers broken – and they were a great couple – still are. They even have a child with issues and that has not had the sometimes negative effect which sometimes occurs. The “Dealbreakers” in this case merely served to form enough resistance – so that one who overlooked them was sufficiently taken by the deeper qualities to override that resistance.

    Sure they were shallow – and they were overcome by depth. Once in a while a good story… Character won out.

  4. Dating Goddess Avatar


    They were: He had been married, he had kids (2), and he chewed tobacco! Not what she thought she wanted, but, as you say, character won out. And what a winner he is! (No tobacco chewing any more.)

  5. Cal Avatar

    What Marina says, when I ask a woman out if she says she is busy that particular day, that is it for me, I will not ask again. If she wants to ask me out at a later date, that is fine and I welcome it. Best of luck to all.

  6. Pam Z Avatar

    I’m not sure that I come through to some of the men that I have come across on these online dating sites. I am honestly too honest, which most guys find to be threatening. I become leary if I ask a question and they take to long to answer the question. It seems to be a simple enough question that should take the average fifth grader to answer in a few seconds. When I am left to wait while they come up with an answer, I have already decided that if it took him that long to figure out what year he was born, then it is clear to me that he is not 44 but 64.
    Just love the fella’s who never post their photos. Explanation of why not? He works for the government. Hello. I didn’t know that James Bond was an actual person. Just a movie character?Now if he said he work’s for the CIA, then I suppose he would have a legitimate excuse for not posting his photo. Bottom line is, that if his live is that secretive, can only imagine what other secret’s he may posses. No photo warrants a red flag for me.