The Ten Best Dates – Cracking the Code

Recently, as I lamented the cost of going on dates and how it really is a ‘rich man’s game’ now, I had reason to reflect upon the ten best dates I’ve ever had.  Why ten?  Our culture seems to think everything comes in groups of tens.  I blame the Europeans and their insistence on using the metric system.  I digress, as I often do, so ignore the blathering.

There is purpose to what might seem like a bit of nostalgic drivel.  Within these ten dates, all of which are fairly different, is a hidden formula for the absolute perfect date.  Of course this formula has variables, such as the woman to whom I’m attempting to pitch woo, the season and the relationship up to the point of the date.

It is sincerely possible that some of the women I went on these dates with will read this and I want to state that this is simply a selection of dates that have stood out in my mind.  More recent events stick out more than later events.  These dates were also selected because I do think they fit a very specific pattern which I will discuss once I’ve described the dates.

Sushi and Sake


For a long time, I was the guy who turned his nose up at sushi and declared it unfit to be eaten because of its raw state.  I could not imagine it being good.  How could it, it was raw!  I overcame my objection to it and loved it.  Unfortunately for me, I’ve never had experience with sake.  On one date, the woman I was going out with took me in hand and we selected a sake to bring with us to a sushi restaurant.  She took the time to explain the different types of sake to me and share the experiences she had with sake.


This date combined good food with an opportunity to stretch my own personal knowledge and experience which made me very happy.  It was a fresh and novel experience.

Sunday Morning Cartoons


Classifying this as a date is stretching it a bit.  Before one woman and I started to officially date, she would come over to my place every sunday morning and we’d watch Animaniacs, Pinky and the Brain, Earthworm Jim, and Freakazoid together.  I had a huge unbearable crush on her and looked forward to her coming over each week.  I didn’t have a bed at the time and slept on the floor of my studio apartment.  She’d gather blankets and lay next to me as we ate bagels and watched TV.   It wasn’t until i accused her of thinking I was some sort of eunich that it came out that this was her expressing her interest in me.


Within this experience, I discovered that I like to be comfortable with the person I am on a date with.  There is no reason why I can’t feel like I am not only doing something that has a romantic context attached to it, but also have the warm feeling of being with someone that is also a friend and companion.

Once More With Feeling


Those who know me know that I love Joss Whedon.  Those who know me know I love surreal crazy events and the Buffy Sing-Along was such an event.  I didn’t have to drag my date to go see it as she wanted to see it as well.  We met friends there and were thoroughly entertained.  During the lead up to the show, the group putting it on called for volunteers to play out scenes from Buffy the Vampire Slayer (tv show).  Before I knew it, my date was up in front of the entire theater emoting and hamming it up like the star she was.


Expect the unexpected and prepare to applaud, hoot, and holler like a true fanboy.   If at all possible,  providing my date with a venue to showcase herself in a way she wants to be showcased is simply amazing.

Renaissance Fair

How do you know the first date went well?  When the following day you spend all day together at a fair.  I absolutely love the renaissance fair and I don’t care who knows it.  Being able to take a date there for the first time was possibly the most fun I’ve ever had.  She had been there before but being able to share the experience opened the place up and made it even more magical to me.


Sharing an interest in an activity and experiencing with someone else, heightens the experience and creates an everlasting bond.

Company Party

My company threw a large thank you party for the IT and Finance departments for the hard work put in closing the books for the year.  It was a suit and tie sort of party and we were allowed to bring a spouse or date.  Normally this would be something I’d skip (see the previous posts regarding social anxiety for an explanation) but I couldn’t help but think the experience was going to be fun.  Bringing a date was something I was reluctant to do, but I wanted to share the event since it was supposed to be a very nice dinner.


I never felt more comfortable with bringing my personal life and work life together.  It transformed what I saw as a casual dating relationship and put a spotlight on it. Breaking the routine of the dates, upping the ante, helps put a whole new spin on the relationship.

Milwaukee Valentine’s Day


Living in Chicago makes Chicago kind of boring.  Milwaukee seems exotic and exciting.  So one Valentine’s Day, the woman I was dating and had a romantic getaway at the Pfister Hotel where we enjoyed their Valentine’s Day meal special, but also enjoyed a night at The Safe House.  If you don’t know what The Safe House is that is good, that means it still is a safe place to go.  We had a blast going to bookstores and wandering around the city of Milwaukee.


Setting aside time specifically for romance does not have to be cliched and evil.  Also, changing the normal venue makes something that is commonplace, going to a bar, into something special.

Accidental Pizza


This one is a bit odd.  I had scheduled a date and on the day of the date, she got in a cycling accident.  I can’t even remember what we originally were supposed to do.  I assumed she wouldn’t want company at all but she said she did but couldn’t really leave her apartment.  I picked up pizza for us and we watched Grey’s Anatomy together.


Having your date get injured is awesome! Wait, no.  Stop. Cross that out.  It isn’t awesome, it sucks. So why is this one of my ten best dates?  This date revealed to me a level of care that I had for this person that I didn’t know was there.  At that point, all I wanted to do was make everything okay.  As a nihilistic individual who pretty much believed love was dead, it created Spring in my soul.

Polka Dancing at Mayfest


In my neighborhood there are two major German festivals.  I honestly can’t remember if this date was on Mayfest or German-Americanfest.  Since Mayfest is shorter and they are essentially the same festival just in different months, I’m going with Mayfest.  On this particular date, we had gone over to Mayfest and were drinking a few beers while listening to polka music.  The wonderful thing about polka music is it really makes you want to dance.  Okay, maybe it is the beer that makes you want to dance.  Either way, my date and I were able to fairly admirably perform dance moves together in a way that was both fun and not destructive to the people around us.


Spontaneity, whimsy, and just letting go created a moment of pure fun.

The Wicker Man


My date really wanted to see a midnight showing of The Wicker Man at The Music Box Theater.  I had no idea what it was but was willing to be dragged to a movie.  At the theater we ran into a mutual friend of ours and the three of us enjoyed the special director’s cut of the movie.  It was incredible.  I was astonished I hadn’t ever heard of this movie before.  We talked about it for hours afterwards.


Being pulled from my general comfort zone to experience something that I may have overlooked and being able to share that moment with a date created a lasting and beautiful memory.

Puttanesca Dinner


I like to cook, it is one of my better honed skills.  I can’t say that I enjoy having people cook for me, in general because I like things done in a particular way.  On this particular occassion my date wanted to make pasta puttanesca for me.  I turned my kitchen over to her and watched her cook.  I will go on record that watching a woman who knows how to use a kitchen is one of the sexiest things ever.


This one is easy.  Cook with the people you are dating.  I learned so much about her temperment, flexibility, organization, and stamina watching her cook.


The best dates I’ve had all seem to revolve around leaving my comfort zone.  Not to the extreme, but just enough that I felt off-kilter a bit.  In this environment new and unexpected events transpired and emotions developed.  Additionally, these dates were  about sharing something, particularly an experience, but in other cases, knowledge.  Putting my date in the role of expert and educator took a lot of pressure off of me on trying to be entertaining.  This only works if the woman likes to share, explain, and show off a bit, of course.  I did mention there are variables in this formula.

The other critical element, that I seem to have forgotten lately when planning my tried and true dinner and drink dates is a good portion of these dates broke the cliche.  Spending all day with someone on the second date, making ‘date night’ Sunday morning, or turning an accident into a chance to be kind and caring are examples of how a great date can be something unexpected.

I will at some other time rant about the actual cost of dates for men in their late thirties, but the fact of the matter is most of these dates were cheap, but did not feel cheap.  Making food at home, attending free street festivals, and company events really are cheap, but what you do at those times, the personality you exhibit are what truly make those moments shine.

While there may not be a date that is ideal each and every time, there are elements that can be applied to all dates.  Essentially the date itself should not outshine the person I am with.  I’d love to hear stories of other people’s favorite dates and what made them so memorable and good.