7 Ways to Create the Perfect Date

My two favorite dates occurred in high school, and they gave me insight in to what makes a good date.

It is sad that my two favorite dates occurred in high school. (opens in new tab) Luckily, they gave me insight in to what makes a good date. (opens in new tab)

In 10th grade, I went to the pumpkin patch/Christmas farm with this girl, Samantha. We checked out the holiday décor (opens in new tab) after a country drive on a crisp fall day. I was shattered at the end of the date when she told me she just wanted to be friends. (opens in new tab)

The following year I got mixed up with a girl named Tara who had a boyfriend away at college. (opens in new tab)

One late February afternoon we walked to our school and climbed to the gym roof. We sat together watching the sunset, huddling closer and closer as it got colder. (opens in new tab)

But I was too young and stupid to know I couldn't break her up with her boyfriend. (opens in new tab) After hanging out extensively, things blew up and our friendship didn't survive it. (opens in new tab)

Here is what made those dates (opens in new tab) great:


We didn't plan where to go, set up a time, etc. We went out with loose ideas of our destinations-we went where our spirits guided us.

These days, I feel pressure to know what we are doing and where we are going, or else it looks like I don't care. Now, time is so valuable to everyone, we must "slot in" dates versus getting together with no particular place to go.

No Sex Pressure

I didn't have sex until I was 18, (opens in new tab) so I wasn't thinking about it during the dates. Sex complicates everything for me-even a first date.

By now, most of us have sexual issues (opens in new tab). Bad things have happened to us, we've lost trust (opens in new tab), we've become jaded, etc.

A Friendship Base

I knew both of these girls as friends for a while before hanging out alone. So hanging out didn't feel like a "date".

Post-college, it's tough to build a friendship with someone before you go out with them. (opens in new tab) You're stuck in your office 9-5, and additional engagements take up your time. The women I become friends with remain friends. The women that I go on dates with are romantic interests. If it doesn't work out, they don't become friends. (opens in new tab)


Both of my favorite dates were free. (opens in new tab) In a way, taking a country drive, or a walk, or watching the sunset is more intimate because you only have each other to focus on versus a show, a waiter & dinner, etc.

A Little Help from Nature

Nature sets the tone for so many dates. (opens in new tab) Getting caught in a rain storm can be just as memorable as a stroll on a perfect day. The crispy fall day and the cold sunset were perfect backdrops for my dates, and a major part of the memory. Fall weather and winter sunsets are still romantic to me because of those experiences.

A Positive Attitude

Back then, I thought I could win over any girl. I went in to every romantic situation with high hopes. By now, I've learned that's foolish-so I go in with expectations below sea level, and this usually dictates my mindset during a date. (opens in new tab)

Unveiling a Comfortable Spot

My dream romance is all about enlightening one another.

On both of these dates I shared special spots and experiences with the girls. The pumpkin patch is a place my family went to annually during my childhood. The top of the gym was a location my friends and I visited regularly and it was the first time Tara went up there.

My "special" spots these days don't feel as dramatic (opens in new tab), and they are not a part of my childhood like the pumpkin patch. The only way to solve this is to get out more and find more wonderful places to share with girls.

I'm struggling with dating in the "real world." I have more things to worry about and it drains my energy. The real world makes it tough to develop a relationship.

It's no longer easy to see the same person twice two weeks in a row in a non-dating setting. Maybe the corner coffee shop you both visit and common friend groups solve this problem, but it's still tough.

I have to make adjustments to date better in the real world; I'm just not sure how I'm going to do that.

Special dates wouldn't be special if they were common. (opens in new tab) Most dates are ho-hum. But, it would be nice to have a memorable date once in a while.

What is the best date you've been on and why? Do you agree with my thoughts above, and how do you think I should adjust to have the opportunity for special standout dates again?

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