Dating Advice

For Guys: When Grand Gestures are NOT Appropriate

I Love You So Much

If you’ve been reading my blog for any bit of time, you might come to realize that there is a wealth of information in the commenting section of different articles. Sometimes I’ll turn a commenting conversation into an article like I have today just because I feel like many other people will benefit from the content. Today, I wanted to share a comment from a reader who is frustrated with the fact that his grand gestures are not being received positively by women he is pursuing. I share below when a grand gesture is appropriate, and what the difference is between “effort” and “planning,” as they are not synonymous.

I also thought it appropriate to share this just because I wanted to clarify myself. I talk a lot about the importance of pursuing women and putting in the “effort,” but exactly was is effort? I feel I’ve been vague in that regard. This is my way of giving you more specifics. So here goes…

Reader’s Comment:

What big walls? Well, the craziest one was a girl who was cute to look at and charming to talk to for the first date (just a picnic on our arctic beaches). After such charm I got a little excited and wanted to show her that. So I took her to dinner again but this time, each course was at a different spot downtown and each had a little piece of some innocent, corny poem. It sounded like a great idea, but she started to get defensive about “being fussed over” and by the time we got halfway through, she started to get aggressive. After I left, one of the waiters at the restaurant told ran up and sympathized, I thought I might have said something wrong, but he didn’t think I did, so just massive confusion there.

A second one was similar in timing, third date, I was pretty charmed so I went all out again. That one seemed to work, as I continued to see her, but it seemed to set a precedent that I had to continually one-up myself, it just never seemed to satisfy; just not good enough.

These are the two big ones, but not the only ones. Generally, anything special or different I try to do to make her feel special is met with indifference. I’m an expert at a good first impression, but the second, third and forth ones never seem to go right…

I guess I’m just confused as to the difference between planning an evening or something and putting out a good effort. I thought planning WAS effort.

My Response

    I guess you can scare a girl off when those grand gestures are done so soon, probably because deep down women want to be appreciated for who they are and not just how they look, and given the timing of your grand gestures (second date and third date), they may feel that you must be infatuated with them and not really know them. Women like being put on a pedestal, but it’s hard for them to love someone who puts them on a pedestal because they are afraid that once you get to really know them, you’ll run away. It’s much more keen to wait until you’ve secured them (dating them exclusively) to put out the grand gesture.

    In the meantime, pursue them consistently, give them lots of time to get to know you/you get to know them, and make it a safe place to open up. Being a good listener, buying her a small gift that she had mentioned she liked on one of your dates, those kinds of things turn a women on way more than grand gestures you could do with anyone, just because in the back of their mind, they are thinking, (with small sweet subtle gestures) this guy is listening. He really listens. He is really taking the time to get to know me. He’s thinking about me when he’s not with me!

    Save those special evening plans for anniversaries in the future:) They are brilliant, but the timing is wrong. She has to feel like she has earned them, like you’ve gotten to know her well enough throughout some time and you’re doing it because SHE’S SPECIAL, not because you want to just IMPRESS HER.

    That’s the big difference. In the early stages, planning is not the same as good effort. Good effort is calling consistently, texting consistently, flirting and complimenting regularly, listening well, paying attention, securing consistent dates, letting her basically know that she is on your mind, but at the same time, you’re still in the early stages, so you’re not giving her the GREEN light 100%. You are making opportunities to get to know her to see if she’s worthy of taking to the next level (exclusivity).

    Big tactics to impress at the beginning stages just make a guy look like he’s willing to do this for any girl, just to impress her. Again, she wants to feel special. Hold off on those grand gestures, and go for subtle sweet gestures (again, buying her a small gift just because you thought of her and she had mentioned something in a conversation) Anything too big at the beginning will come off as an act of desperation, like you’re willing to do anything just to get ANY girl. It reads this way just because you’ve not had ample time to really get to know her.

    It’s akin to a musician writing a song about a women he’s only just met, and announcing it when he goes on stage, “This is dedicated to ________.” He’s thinking he’s nailed it, she’s thinking, This guy is crazy. He doesn’t even know me.

    I think grand gestures only work in the beginning if they are done in a silly/joking fashion, like a guy teasing a woman, and most of the time only outgoing, confident, naturally charming men can pull this off. It has to be done with an air of confidence and a smile.

    Remember the effort must come in the form of actively trying to get to know her, not trying to impress her. The beginning stages must be a process of mutual discerning, meaning, there’s not one party who is trying to win the other, while the other is making the final decision of whether or not it goes forward. It should be the girl testing the waters and the guy testing the waters. When you do anything to make it appear like she has full control of whether or not it moves forward, it shows a lack of discernment on the man because it shows he’s been won over by charm and beauty and has not taken into consideration character, integrity, goodness, as those things take TIME to discern (Takes a lot longer than a couple dates that’s for sure). You have to show interest, but you have to always behave in a way to show that this early period is meant for getting to know one another, not trying to win her over. You shouldn’t be sure you want to win her over yet.

    Does that clarify things a bit?


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I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

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  1. hunter

    ….man says he gets them with his looks, but, does he continue the compliments??..He has to tell her how beautiful she is, almost every time he sees her. Almost no other word lights up a woman more, than, “beautiful”.

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