Sunday Morning Soliloquy - Musings of an Urbanite: The Best Dates I've Ever Been On

Thursday, January 27, 2011

The Best Dates I've Ever Been On

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Keeping With The Dating Theme

Earlier this week, while I was in my grammar class, I was thinking about this blog. I always write stories about negative experiences (because I think they're funny), in class I made a silent declaration to put a positive spin on a blog post for a change. In keeping with the dating theme, I decided to write about my best dates ever!

The Kid
Some time ago, I dated someone significantly younger than me. My friends and I had many nicknames for him (Research and Development, Tragic Yet Beautiful) but my favorite was "The Kid". The Kid and I started dating secretly, mostly because I was embarrassed about our age difference, but also because we worked together.

The Kid wanted to do something special for me. I normally planned everything and he wanted an opportunity to do something for me, create a special evening.

He made a reservation at Lula Cafe. When we arrived, the restaurant was packed, but luckily, I happened to know the bartender. After just a few minutes, we were seated at the table in the picture window. We had two bottles of wine and an amazing dinner. Throughout dinner, The Kid held my hand under the table and gazed longingly into my eyes. Normally, those things annoy me to no end, but oddly, on this night, I enjoyed the attention.

Our romantic dinner went on and on until we closed the restaurant. Next stop - The Green Mill. A Chicago treasure.

Green Mill, 2

Very much like Lula Cafe, the Green Mill also felt magical. We found a fantastic table, he ordered a Makers on the rocks and I a Basil Hayden's on the rocks. Bourbon drinkers rule.

After The Green Mill, we went back to his apartment. This made him very happy because I often complained about how crappy his apartment was and refused to go there. The Kid had painted his bathroom in honor of my visit. I was moved.

As I type this, I realize it doesn't really sound like the best date ever, but when I was trying to think of excellent dates, this was the first one that came to mind. I am finding that I am unable put it into words, but the whole night was dreamy, it felt as if we were in a love haze. The Kid hit a homerun with his date night.

My Surprise Date to Las Vegas
Quite the opposite of The Kid, most of my adult life I dated men older than me. When I was 24, my boyfriend was 12 years older and I used to call him Boss. I am trying not to give away who these people are because they're all in relationships and I don't want to be tacky, just trying to paint a picture.

Boss and I dated for two and a half years, in fact, he remains the best boyfriend I've ever had. Not my favorite, but the best - there is a difference.

One year for his birthday, Boss planned a huge night out. We rented a limo so Boss would not have to drive, we made dinner plans, made plans with his friends, my friends, etc. It was starting early and we planned to go out all night! I was thrilled (because I was 25 and drinking for 7 or 8 hours appealed to me at the time).

SUV Limos

Boss picked me up from my apartment in the limo and off we were for our extravagant night! We were heading to a new restaurant in the south suburbs that he really wanted to try. I had not heard of the restaurant, and I found it odd that we were going to the suburbs, but it was his birthday so I did not question the choice. Our friends were meeting us after dinner at a bar back downtown and from there we were going to a club - I was ready to let the good times roll!

We got on I-55 going south and there was a lot of traffic, Boss started to get anxious. As traffic worsened, our driver was also becoming nervous. The anxiety in the car did not make sense to me, why was it was such a big deal if we were a little late for our dinner reservation?

Even as we got off the highway and headed south down Cicero, I still did not get it. As we pulled into Midway airport, I still did not get it. As our driver opened the door of my limousine and Boss urged me to get out of the car, I was STILL confused. I thought we were going to dinner?

Boss was taking me to Las Vegas for his birthday and I failed to see any of the signs. I protested at first! What about dinner? What about our friends? What about my job?

The details had already been taken care of. All of my friends knew, no one was meeting us anywhere, they had all kept it from me. Boss had even arranged with my friends from work and taken days off for me from both my day job at the advertising agency and from my weekend job.

And off we went, to Las Vegas! It was the best date because I had NO clue. And, it wasn't even MY birthday but I still got the surprise.

Puppet is someone I dated for a long time...a long time ago. Puppet was my nickname for him and it was also his nickname for me. Confusing if you were in our company.

Our first date was our best date. Both of our first dates were our best dates but I prefer the actual first date. (I count our first two dates as our "first date" because we didn't think a lunch date counted as a real date.)

I met Puppet out one night while I was with my girlfriends and he was out with his friends. We met at a hotel bar, everyone had a few drinks, then everyone left to move to a secondary location. On the way, there was a high speed chase, almost a big fight, rumors of a gun, the police showed up, tossing of contraband took place, and finally everyone arrived safely in Wicker Park for more drinks.

I gave Puppet my number the night we met and demanded he call me again - and I was NOT kidding. The problem was, we met the Thursday before Christmas, and with the hectic holiday schedule we were both committed to, arranging a time to meet proved nearly impossible. I remained hopeful that he would call and waited anxiously by the phone (did I mention, I don't call men). The first couple days, Puppet did not call. Finally, on day three, Puppet called. Rejoice!

Generally, I am not a pushy girl when it comes to dating, but when Puppet called, I insisted we meet even though he had plans. I did not want to wait until after the New Year because I knew we would lose the momentum, or even worse, I would lose interest.

We met for lunch the day after Christmas, it had to be lunch because he had plans with his family that evening. He picked me up at my apartment and we went to RL for lunch. The date went quite well.


From the moment Puppet and I met, it was as if we had known each other our whole lives. It felt natural almost instantaneously. The day went over so well, that after our long lunch, we decided to take a stroll down Michigan Avenue. From there, we decided to go to Starbucks to talk. From there, he invited me to dinner with his entire family.

That was when I had to draw the line. I did not want to meet his entire family on our first date. I went home and we saw each other again the next day and pretty much every day after that for the next few years. Let's just leave it at...It was a good first date.

Related Readings:
  • Four Steps To Floor Your Dream Girl On Your First Date - Or Your Money Back!

  • Graham Elliot - Great Date Place!

  • Peninsula Chicago - Chocolate Bar Another great date place!
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