You CAN Do Too Much

A recently-divorced friend of mine has started online dating recently.  And this weekend she went on a stereotypical “perfect” date.

The guy took her to a really nice restaurant, brought her nice flowers, took her to a movie after, held her hand, was a gentleman…

Checked all the boxes, right?

Sounds like he’s on the right track, doesn’t it?


I expect my friend will blow this guy off in another couple of dates.  And, from something he said on his date with her, it wouldn’t be the first time that a woman walked away at the five to six date mark.

So, what’s this guy doing wrong?

He’s doing too much.  (Of the wrong things.)

Now, granted,  I was not on the date.

But I’ve been on those kinds of dates.

And what I’ve found is that certain guys try too hard to check the boxes and fail to date the woman in front of them.

For example, turns out my friend was pretty uncomfortable with this guy she doesn’t know that well insisting on holding her hand through the whole movie.  “Insisting.”  Her word.

Now, if you’re watching a movie with someone and you start to hold hands and it just naturally continues?  Fine.

But if you try to force intimacy by holding hands with someone.  No.

And, this is just me, but generally any man who brings me flowers on a first or second date is someone trying too hard and is generally someone who doesn’t read women that well.

Flowers are a shortcut.  They’re virtually meaningless at this point.  Unless we’ve had a conversation about a specific flower, they’re a throwaway gift.  A knee jerk reaction.  “I’m a guy, you’re a girl, so I give you a dozen roses.”

(Not to say that certain women don’t expect men to deliver on those clichéd expectations.  That’s the challenge of dating.  You’re always dating an individual not a gender.  So what doesn’t work for me, works perfectly for another woman.)

This guy probably does well on getting second and third dates.  He’s articulate, successful, has manners.  But at some point women probably start to feel a disconnect.  Because the more he gets to know them and the more he should start to tailor activities and conversations to them, the more he probably continues to follow a one-dimensional, standard approach.

(Like on The Bachelor when one of the final girls finally realized that the guy didn’t care about who she was or know her at all.  He wasn’t dating her, he was just dating a generic woman.)

So, if you feel like you’re this guy, what do you do?

Back off a bit.  Try to find out what interests her.  Don’t give everything at once.

You know how they say that men like the chase?  I think women do, too, to a certain extent.

So, treat her well.  Be a gentleman.  But if she expresses an interest in a cheap Asian restaurant, go there instead of the expensive Italian place.  Or do some completely random activity with her instead of your standard date/movie.

To me, the key takeaway is that there aren’t a set of boxes you check to succeed with a woman.  You have to go with the flow.  Read her and react to her.  That’s how all good relationship work.  Give and take.  Back and forth.

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