Why Testing a Man Will Almost Always Backfire

Name: Pilot Girl
Comment: I met a guy a few months ago through a friend. He’s a little younger and works crazy hours in the investment banking industry. I wasn’t interested at first because of the age difference. I turned him down a few times before finally agreeing to go out with him and almost cancelled our first date. I’m glad I didn’t because it went really well and we had a really good connection.

He was very consistent about seeing me again and again. He didn’t let more than a day go by without texting or calling to set up the next date. Twice he called me very last-minute to see if I wanted to grab a bite or coffee after work (when his boss would unexpectedly let him go home early). I agreed to meet him both times on the fly and we had an amazing time talking and getting to know each other. But after the second time I let him know that I would prefer a few days notice for dates. From then on he started to schedule our dates in advance.

Here’s my issue. He called last Thursday and asked me out for dinner/movie in the next couple of days (our 6th date). I told him I was free on Friday (next day) and Sunday. He replied that either one of those days worked for him and that I could choose. I chose Friday and we made plans.

A few hours before our date he called to say something came up at work and he had to work late. He immediately suggested we reschedule to Sunday plus gave me Saturday as an option too. He caught me off guard so I initially agreed to Sunday as I was busy on Saturday.

Then I thought about it. Something didn’t feel right. That saying by Dr. Phil “you teach people how to treat you” popped into my brain. If I let him cancel on me at the last minute so early on in our courtship then will he think I’m a pushover? Lose respect for me? Do it again next time?

It was a very painful decision (because I really wanted to see him) but I texted him back and said I forgot about plans I had for Sunday (lie) and let’s try to connect next week. I wanted to send a message that canceling at the last minute was not OK and the consequence is that he won’t get to see me that weekend. He texted back right away with “Why are you bailing on me? But OK, whenever is good for you.”

He didn’t wait until next week to contact me. He texted on Sunday to say hello and then again on Wed evening to see if I was free for a bite (again last-minute because he finished work early). I was happy to hear from him but I was literally in the middle of having dinner with a friend. I told him I was busy and I’ll be happy to do it another time. He texted back “For sure!” but didn’t offer up an alternative. It’s now Friday and I haven’t heard from him since Wed. We don’t have any plans for this weekend and I feel like I blew it.

I feel horrible about telling him I was busy on Sunday when I wasn’t. I’m starting to think that this disingenuous move derailed our dating momentum. But as a woman who’s dated her share of jerks, players and flaky guys I find it hard to strike a balance between being flexible and being assertive. When do I let it go? And when do I put my foot down?

My dilemma is this: Did I do the right thing by making a stand when he cancelled on me at the last minute? Or did I need to be more flexible knowing that his job is very demanding and unpredictable? Who should make the next move? I feel like he’s pulling away (maybe due to my perceived lack of interest) and I’m really unsure about what (if anything) to do next.
Age: 42
City: Toronto
State: ON

 

Did I do the right thing by making a stand when he cancelled on me at the last minute?

No, you didn’t. You screwed up. This is a classic example of the way many men and women sabotage themselves by implementing tests. Everything appeared to be moving along nicely. Then you had to go and invoke some stupid rule and create a problem where there was none. Now he’s sitting back and waiting for you to initiate a date. So do it.

You’re sitting there waiting for a guy to screw up. When he doesn’t, you create a situation that you can point to and use as evidence that all men are this or that. You need to get over that. You can’t be looking for monsters around every corner.

I’m going to guess that your suspicion stems from the fact that this guy is younger than you. If the age difference was significant enough for you to be hesitant about dating him, I’m guessing he’s not just “a little” younger. He’s likely noticeably younger than you. If that is the case, then you should be suspicious of his motives. Two to three years? Eh, not a big deal. But if this guy is in his mid to late thirties, then you’re right to wonder what his intentions are. That doesn’t mean you shouldn’t date him. It just means that you should proceed with caution. This is one of those situations where critical thinking should come into play. Ask yourself this:

Why would someone his age want to date someone your age?

He could be totally sincere and interested in something substantive. You will only know that after you spend time with him. If you’re not able to set aside whatever questions you have about a man’s sincerity, then you should remove yourself from a situation. Give him a chance. A real one.

For the most part, the tests and traps that people use to determine someone’s character or interest prove nothing. All they provide is a false sense of confidence and security. They never consider that, as humans, we become adept and determining the right things to say and do in order to fulfill an agenda. It doesn’t matter if your goal is to get a free drink at a bar or get someone to commit or into bed. We say what we know people want to hear. We present ourselves in a specific light in order to get what we want. Sure, that guy will pay that bill or compliment you. Not because he’s so bowled over by your presence but because he knows not doing it will not get him what he wants. That’s what men and women do.

I have said this before: people who research their dates or who implement trite dating advice they’ve heard from charlatan dating coaches or their friends do so because they don’t trust themselves. They haven’t learned from their past mistakes. They don’t listen to whatever internal voice that that is telling them that something is wrong. I assume that the reason people do this is because they are hoping against hope that this Unicorn that has presented itself is real or because they need to prove something to themselves.

If you find yourself questioning somebody’s motives right off the bat, there’s a reason. That’s your brain poking at you and saying, ‘Hey…based on past experience and what we know to be typical, something about this isn’t right.”

I’ll say it again: Observe. Compare. Deduce.

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34 Responses to “Why Testing a Man Will Almost Always Backfire”

  1. AnnieNonymous Says:

    Wow, this woman screwed up. This guy did everything right. He didn’t lie about having something come up at work. It’s not like he blew her off or had a scheduling overlap.

    I think there are two issues here: One is the OP’s weirdness about needing so much advance notice when clearly her life isn’t all that demanding (she was able to meet him at a moment’s notice for coffee). I suspect she recently got out of a relationship where she was working around her partner’s schedule or whims. It’s not wrong for her to try to make changes to avoid that in the future, but she’s going too far.

    The second issue is the fact that this guy has a zany work schedule. That’s a legitimate dealbreaker for some people, for the reasons that are making the OP nervous. If I’m on the fence about dating a guy, I’ll base my decision on his work schedule. If it’s easy for us to get together, I’ll give him a chance. If it requires a lot of planning or if he has the sort of job that doesn’t have a consistent schedule, I let it go. I’m not in the market for a boyfriend I won’t get to see very often. Obviously there are exceptions to every rule, but there’s a reason that relationships with workahollics are really hard to manage.

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    • AnnieNonymous Says:

      I’ll add: She needs to be a bit more forthcoming. When the guy texted her while she was already having dinner, “Busy!” doesn’t suffice as a response. She should have said, “I’m already out to dinner with a friend, but how about we meet up for drinks later tonight?” or offered some other alternative. I don’t think she realizes that after canceling on him over the weekend and now turning him down outright, she has rejected him twice in a row. It’s her turn to initiate a phone call and propose a date idea. It’s like she’s trying to change him without realizing that this is what it’s always going to be like to date someone who works in finance.

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  2. Matt Says:

    “Or did I need to be more flexible knowing that his job is very demanding and unpredictable?”

    YES. You knew for a fact that he had unpredictable hours, and still you let paranoia get the best of you. I mean seriously- you let a message from DR. PHIL sabotage you when things were going smoothly?!?

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  3. wishing u well Says:

    I agree w/Moxie and AnnieNonymous. Yeah, if you want to attempt to salvage this, OP – it’s now your turn to make a serious effort, consistently follow through, and let this guy know that you’re sincerely interested in him. Even so, it may be too late, but I hope it isn’t. At any rate: now you’ve learned something important. I wish you well.

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  4. joe-f Says:

    As an ex-banker, let me tell you he didn’t cancel on you at the last minute, his boss did. Those of us in banking know that any minute our boss can call us and tell us to work regardless of whatever plans we had made. So cut the guy some slack. He sounds genuine so at least give him a chance unless you tell me you can’t deal with his crazy schedule, which is a legitimate grip.

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  5. The D-man Says:

    I detest manipulative behavior and will move on if I sense it in a potential partner. Not that I’m perfect. I went through a short phase of doing crap like this. It blew back on my once and I decided never to do it again.

    Now I just say what I want and expect and if she has different needs or expectations, I move on. A relationship built on manipulation is toxic.

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  6. GuyDatingAbroad Says:

    This is why I don’t date here anymore. I know not everyone is as neurotic as the behavior exhibited by the OP, but for the majority of my experiences, they are.

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  7. Mickey Says:

    Whats with the ‘i come first’ test? You’re newly dating and sorry to tell you but you dont come first, yet, his career does, as it should. You say he’s very interested, he acts as such and you have a great time together, so what’s the problem? He’s got a demanding work schedule, you knew that, yet you’re standing firmly on the put me first pedestal. If scheduling is an issue, date someone with more predictable work hours. Stop giving him a test he doesn’t even know he’s taking.

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  8. LaMotta Says:

    I disagree partially with Moxie. I think it was reasonable for her to cancel the Sunday plans. You do need to think about the expectations you create when you let someone act a certain way. If she was worried about always being at his “beck and call”, then she needed to push back.

    Besides, for all we know, the “thing that came up at work” could actually be another woman.

    But it doesn’t really matter. The cancellation wasn’t her mistake; her mistake was not to then come back with her own proposal for a date to “balance it out”. This is where the OP didn’t realize that SHE had been trained — to expect him to do the work to plan and propose dates.

    So overall she ends up acting based on being paranoid about the guy’s behavior/intentions, without taking the intiative herself to fully hold up her end of the “deal”.

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    • Matt Says:

      “You do need to think about the expectations you create when you let someone act a certain way. If she was worried about always being at his ‘beck and call’, then she needed to push back.”

      In that case, instead of being coy and “clever”, she should have been upfront with the guy. “Hey, I know you have a unpredictable schedule, but I’m not comfortable having to rearrange things at the last minute like that. Can we maybe discuss things in case something similar happens in the future?”

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      • TW Says:

        You mean communicate? Openly? People who do that routinely probably don’t need this website….

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    • AnnieNonymous Says:

      There’s no absolute rule for that sort of thing. If both people are working standard 9-5 jobs, I don’t think there’s anything wrong or weird about spur-of-the-moment dates. The issue with the OP’s situation is that in order to date, she’d have to work around his schedule and he’d never be able to do that for her. It’s not necessarily a bad thing that the guy has a good job, but it’s a decision she has to make.

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    • Jim Says:

      “Besides, for all we know, the “thing that came up at work” could actually be another woman.”

      Wow, so this guy has been CHASING her, and you’re assuming the worst of him – just like the OP. My advice would be to the guy – she isn’t worthy of a man like him, and he should cut and run ASAP.

      Especially because she’s FORTY something. If you gotta deal with BS games, may as well get them from a younger, hotter woman.

      PS – I’m 40+ and very happily married to a woman in my age bracket, so don’t think I’m bitter! But why should a man deal with games without getting something in return?

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  9. hammersandnails Says:

    I would certainly take the hint if a girl I had been dating turned me down half as often as you turned this guy down, and I’m guessing your cancellation tripped his bs-o-meter by his response. You are a 41 year old woman who made him beg for a date in the first place, you make dating you intentionally more difficult than it has to be just to satisfy your own insecurities, you lie to him to him, you turn him down often, and you are seriously wondering if you did the right thing “putting your foot down”?

    No woman should have to suffer such an asshole that would ask you if you want to get dinner without two days notice. What a monster. What kind of spineless loser doesn’t just quit his job on the spot if it conflicts with a dinner date with the center of the universe? You’ve got pointless hoops and if a man can’t jump through all of them then “he wasn’t worth it” and it wasn’t “meant to be” and you “deserve better” anyway.

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  10. Alan Says:

    Initiating and paying for the next date isn’t enough (assuming he has been paying the rest of them).

    I’m thinking mandatory head.

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    • Lisa G Says:

      what ???????

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      • CoolDude Says:

        Alan,

        You must be new around these parts. The commenters on this site aren’t particularly known for their sense of humor. You got a chuckle out of me though. Cheers.

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      • LostSailor Says:

        I thought it amusing, if not necessarily worthy of further comment. But now that I am commenting, it certainly couldn’t hurt…

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  11. Marie Says:

    I think you know you’ve made a mistake here. If canceling last minute was standard behavior for this guy, then yes, you should have put your foot down. But it isn’t. It was you that asked for advance planning, despite knowing his hectic schedule, and now you’re upset because one time he had to postpone? You can get away with having unrealistic expectations like that when you’re 22, but at some point you have to be more reasonable.

    I’m guessing by his response to your message that you already had Sunday plans, that text was a bit snarky. He probably suspects that you bailed on the date as some sort of punishment for him working late (which is exactly what happened). I think it’s up to you to show interest now and plan a date if you want to have a chance at salvaging this!

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  12. LostSailor Says:

    I’ll echo Moxie and the surprisingly agreeing commentariat. Yeah, “Pilot Girl,” you screwed up by arbitrarily canceling the Sunday date for a bullshit reason. But your biggest screw up was canceling without offering a specific alternative day. Especially when he texted the next Wednesday.

    Yes, he is sensing that you’re pulling back for what may be a lack of interest, which, luckily, you can fix. If he thinks that you’re just playing games, you’re doomed.

    As nearly ever one else has said, take the initiative and contact him with a specific day and date idea, and acknowledge (without actually admitting) your behavior by apologizing, along the lines of “sorry I’ve been hard to pin down this week, how about meeting me for drinks at X on Wednesday, my treat.” And then be a little flexible about his schedule and don’t flake unnecessarily.

    But as a woman who’s dated her share of jerks, players and flaky guys I find it hard to strike a balance between being flexible and being assertive. When do I let it go? And when do I put my foot down?

    But this isn’t apparently a jerk, player, or flaky guy. Look, you have what seems to be a great guy interested in you with whom you seem to have some chemistry. He’s done the right things, is respectful of your request for a few days notice before dating (though if things go on, you should be more open to a last-minute thing) and you’re “making a stand” and “being assertive” against him? Pilot Grrrl, you’re 42, time to stop playing games. Let it go. And for the love of God stop listening to Dr. Fucking Phil for dating advice. That shit will rot your brain…

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    • Matt Says:

      Yeah. When a girl says “I can’t go out that night” and doesn’t offer an alternative, or just offers up something vague like “maybe later”, then I usually take that to mean “I’m not that interested.”

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  13. CoolDude Says:

    The original poster is 42 years old. That is about, oh, 20 years too late to be pulling this kind of stunt. Dude is better off without her.

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    • Doramin Says:

      Dunno. 42? Maybe she looks like Gwen Stefani? Or Cindi Crawford? Or Julia Roberts? Or Elle MacPherson?

      Or maybe she just thinks she does?

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  14. Speedy Says:

    I don’t want to pile on here but you understand you weren’t doing what that old fraud was telling you to do anyway. Only in your head were you teaching him a lesson. At no point in the real world did that detectably happen. You wanted to “send a message” but unfortunately you sent another message that apparently stated you were busy. If that implies something, it just says you aren’t very interested. There is no connection between that and what apparently upset you that I can see, you are the only person who knows they were related events.

    If “Dr Phil” was trying clumsily to say something it was to be assertive about how people treat you. You did the complete opposite.

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    • Matt Says:

      Indeed. There’s a difference between “assertive” and “passive-aggressive”. I would probably classify the OP’s actions as the latter.

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      • Speedy Says:

        Indeed. I think OP should consider this in depth because she wrote a lengthy and detailed letter about this matter and still didn’t notice (by the end she is still talking about ‘being assertive’, ‘taking a stand’ and ‘putting her foot down’ which isn’t anything she actually did). There is a personal development issue here that is more important than dating.

        Being assertive can sometimes be a mistake but its never a very big mistake to my way of thinking. So you raise an issue that it might have been wiser to let lie? If you are direct but calm and reasonable, there isn’t that much damage you can ever do. Playing games and passive aggression are however incredibly risky.

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  15. Anais Says:

    THERE IS TRUTH to the “you have to teach people how to treat you”. People here will say don’t play games, you’re being passive aggressive, blah blah blah but this is a pattern I’ve seen in dating before it becomes an official relationship. When a woman is available every time a man who isn’t her bf wants to see her or only a day in advance, he starts to take her for granted, and often cancel with vague/generic excuses. Men want to feel like they have to earn a woman’s time.

    “Here’s my issue. He called last Thursday and asked me out for dinner/movie in the next couple of days (our 6th date). I told him I was free on Friday (next day) and Sunday. He replied that either one of those days worked for him and that I could choose. I chose Friday and we made plans.

    A few hours before our date he called to say something came up at work and he had to work late. He immediately suggested we reschedule to Sunday plus gave me Saturday as an option too. He caught me off guard so I initially agreed to Sunday as I was busy on Saturday.”

    Maybe on some gut level, you felt uncomfortable accepting a date only a day in advance(i.e Friday the next day) because from what I gather, this guy isn’t your boyfriend. So just make it a rule for yourself that you need few days notice. So instead of saying you were free Friday or Sunday, you could have just said Sunday.

    “It was a very painful decision (because I really wanted to see him) but I texted him back and said I forgot about plans I had for Sunday (lie) and let’s try to connect next week. I wanted to send a message that canceling at the last minute was not OK and the consequence is that he won’t get to see me that weekend. ”

    It’s good that you didn’t send that text as it would just come off preachy… but if you felt compelled to reschedule you should have suggested the day yourself.

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    • LostSailor Says:

      Men want to feel like they have to earn a woman’s time.

      Said no man ever…

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      • mindstar Says:

        Where do women hear this crap and why in God’s name do they believe it?

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        • Goldie Says:

          Oh, in “The Rules”, of course. Yes, there are women I personally know who actually swear by that stuff. I did read the book. It goes against every ounce of logic and critical reasoning that I have.

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  16. Anais Says:

    We believe it because it’s true. Women have to show men how they wish to be treated. It’s from personal experience and observation of other people’s relationships. I’ve ALWAYS been walked over and disrespected when I had no boundaries in regards to my time whatsoever. I accepted men who would constantly flake out cancel dates, and seemed to be indecisive. And then I’d go out with them anyway the next time I heard from him because I was so overjoyed that I heard from him again. Then I’d get dumped for a woman who wouldn’t accept this type of flaky behavior.

    Men often deny when a woman or another man says things like this so the comments acting as if I’m on another planet don’t surprise me. Oh and I never read The Rules lol.

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    • LostSailor Says:

      Sorry, but you believe that “men want to feel like they have to earn a woman’s time” not because it’s true, but because it’s what you want to believe. No man “wants” this. Some may put up with it, but no man wants.

      It has nothing to do with having boundaries and standards. Women don’t have to show men how they want to be treated (what’s that, Dr. fucking Phil?) or force men to “earn” their time. Having boundaries is not the same as trying to make men jump through hoops.

      Men deny it because it’s not true. You’re not on another planet, you’re just trying to play games that everyone hear sees right through. Sorry, but smart men and women aren’t playing…

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  17. Kim Says:

    She did everything correct by not accepting last minute dates. No matter what guys say about not liking the hard to get game, the truth is that they don’t value what comes easy. Once in a while a spur of the moment date is ok though, just not every time. If he doesn’t think you have a life or other guys trying to days you, he just won’t value you. Playing hot and cold is the only way to go if you want a guy to go crazy over you. Every time I sense someone is getting too comfortable in the beginning, like he thinks he’s finally got me, I’ll pull back. It’s like a magic trick to his behavior, every single time. Suddenly he has to see me, can’t stop telling me how much he constantly thinks about me, etc. And there’s nothing cruel or manipulative about this. If you really like a guy and your not just toying with someone’s emotions, why not? Guys actually love the chase and they get a bit of a rush from this. So if makes you happier to feel desired and it makes him happier to feel like he’s won over an amazing women in the end.

    I think people are confusing what guys want in the moment and what they want long term. Sure, a guy may want to sleep with a girl on the first date. It’s easy, just like it’s easy when a girl is always available and you don’t have to work to impress her. But a guy doesn’t want to be with this girl and he definitely won’t have an obsessive desire to see her.

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  18. Fred Zendrick Says:

    She screwed up by giving him the impression that she was d—ing him around. Most men of quality are attuned to pick up on this. The kind of games she played are indistinguishable from the runaround and no reasonable man is going to waste time telling the difference. If you want to see a guy, see him. Don’t make him jump through hoops by subjecting him to invisible rules!

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