If You Fail To Plan You Plan To Fail Especially On First Dates

I’ve gone on over 125 first dates in five years, sometimes packing two into one day.  Grabbing lunch and then dinner with different guys.  Or doing to an early dinner with one and the driving range with another.  It takes a lot of energy to really get to know someone new, especially in a short amount of time.  To make the most of it, I put in a lot of effort and always brought my A game.

Just like in sales, I prepared for the dates to make sure I a few interesting things to talk about.  Things that encompassed who I am so he could get a snapshot in a short amount of time.  Often times, people talk about things that are no longer relevant so you don’t really get to know them.  One time, this guy spent the whole lunch date telling me all about these different fishing trips, which I noticed were all back when he was in college over a decade ago.

When I asked him if he still fishes he said, “Hell no. I hate it now.”

He went on to tell me a detailed story that involved a girl, his best friend, a stolen boat, a gun and a whole lot of drama.  I lived in Oklahoma at the time.  It didn’t tell me about the person he is now, but it did help me decide to not to go on a second date.

I’m not saying to prepare an agenda, but think about the things that you want him to know about you, as well as questions that will help you find out about him.  Maybe the 25-minute fishing story was because I didn’t ask better questions.

I like lunch dates because for the same reason I prefer to have work meetings in the morning – people are more alert.  By the afternoon, people are tired or get caught up in other projects so you don’t always have their full attention.  While dates are more fun than work, usually, they can also take a fair amount of energy, especially when the guy is really nervous.

I do my best to make them feel comfortable so I can get to know them by the end of the date, which is one of the reasons I don’t have many second dates.  I’m not saying I’m always the one who decides against a second date, but when I do, it’s because I get such a good idea of whether this is the guy for me.

If I can’t do lunch, I like to do some sort of activity to keep things upbeat, like the driving range, bowling, etc.  A couple of weeks ago, I went to a later dinner.  I had meetings all day, so I was schmoozing with people for hours.  Then, I went for drinks with a new friend, which made me even more tired.  By the time I got to dinner in the dark restaurant, I was exhausted.

He was a nice guy, but super nervous and I just didn’t have the energy to carry the conversation throughout the entire meal.  I wasn’t invested in the date, so even though I know he wasn’t the one for me, I definitely didn’t give him a chance because I wasn’t prepared.  While making a plan to have fun sounds counterproductive, it actually has served me well through the years.

The attitude I bring into the date can have an impact on how it all goes down.  You know when you are at your best, so make sure your first date plan sets you up for success.

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