I was sitting alone in my thoughts, as I am likely to do, a warmth flashed through my chest due to beautifully reminiscent thoughts about some of my past dating experiences. It was the kind of warmth that paved a way to a non-judgmental experience of another individual completely based on the lovely encounter we had during our date. My smiling, as I sat alone on a bus stop bench, might have seemed a bit weird from a regular passerby, but for me, it was the essence of what I was feeling at that exact moment in time while I reflected on these transcendent periods in my life that would never be forgotten. It reminded me of the connection, humanity, and awesomeness of two (or more if you’re into that – no judgement) people can have when they dismiss their own desires in hopes of finding a meaningful and lifelong connection through dating.
Therefore, my heavy thinking, without the heavy breathing, took me to a place in my mind to relive some of these fabulous moments. And like any great moment, we are akin to rating the moment against other moments and time. Let me invite you along for the ride with me and my ranking of my most beautiful dates in my life.
Disclaimer: Not all dates led to marriage, a relationship, or even sex (not that I was against it) but merely allowed me to appreciate the individual during that romantic, soft, enjoyable, and memorable moment. IJS…
Staying present was the key and having a genuine interest in connection to the person, not the date, was paramount. My heart is full, once again, as I get to relive these moments.
My Top 5 (in no particular order, but, hey, it may appear that way based on how my thoughts are hitting the keypads on my keyboard)…
- Laser Light Show to Journey
- Somewhere on the campus of MSU an energetic display of colorful lasers crossed paths and challenged mental boundaries as lasers of the ’80’s took the form of entertainment for the youth of the era. Memorable to say the least. However, being high as a kite had it’s benefits.
- Dinner under the rain
- When the conversation is amazing, the vibe is unreal, outside temps are cooling, and a downpour of rain with thunder as a backdrop, which you both adore, occurs. Sparks fly and the connection is established like no other. Simple, yet, elegant. It’s almost as if we were dancing in the rain. Superb.
- Marriage proposal
- Mexican restaurant with bomb margaritas, an otherwise normal atmosphere, but the feeling of connection that started the fire towards a marriage will always be remembered as a tear ran down her cheek as I expressed my most vulnerable self. And yes, I married this date, and now divorced, but the moment will always be etched in history.
- Korean BBQ hits a homerun
- Who would have thought cooking your own food could lead to such an amazing experience? Not I. Taken a bit by surprise to what the night had to offer, I couldn’t help but be in awe of the date and the atmosphere. I would cook my own food in a restaurant 1 out of 5 times to recreate the moment captured. Riveting.
- The Lake Shore drive experience
- If you have NEVER experienced driving down Chicago’s DuSable/Lake Shore Drive (#chicagolakeshoredrive) you have not experienced one of the most incredibly scenic urban drives in the world. And when you are fresh off a date of Japanese cuisine and the cabbie is driving for you while you and your date share an embrace throughout, then you just haven’t lived. Start living.
Honorable Mentions:
- First kiss on the Chicago “L” Platform – the train is burrowing by but your focused on the kiss that takes your mind to a different place. Surreal.
- Attending Les Miserables – one of the greatest theatre performances of all time and to view it with a lookalike from the Titanic movie – Kate Winslet – it was sure to be memorable. However, the gazillion dollar price tag of a dinner and theatre keeps this from cracking my Top 5.
- Speakeasy entrance – when you’re part of the Kool Kids and the entrance to the club is through an empty barbershop and the drinks are top shelf. Sign me up any day of the week. #celebritystatus
- Facetime date across the US – She’s beautiful, the restaurant exists in both locations, the flowers arrive on time, and the drinks and dinner are served, accordingly. It’s the next best thing to being there in person. Namaste (praying hands graphic π )
- Double kisses outside of the Junior High – What’s a walk outside of middle school with a group of friends, including your bestie, when you have the opportunity to experience your first kiss, first girlfriend? I wouldn’t trade it for a thing, although, I only had about a buck…29 in my pocket. Thankful for middle school pleasures.
In all of my 30 years of living (plus or minus a number of years of experience) I have had the pleasure, mostly, of going on my fair share of dates. In most instances, each was a great experience, however, there may have been a few duds that I wiped from the canvas of my memories. Again, no judgement, as I’m sure the datee might have thought the same [e.g., “WTF am I wasting my time with this LOSER!!”]. Hey, we all can’t bat a 1000.
I’m appreciative of what life has given to me, taught me, and exposed to me along this journey. My desire is to continue to pass on my experience and that it might touch others in a positive way and remind others of the wonderful experiences life has for us if we only take a moment to reminisce. Granted, challenges will continue to take center stage but do not get caught up in the web of discouragement that is often attached to these challenges. Instead, allow yourself to relive those moments, or vicariously through others if you must, so you can partake in the enjoyments of dating, as well.

I’d love to hear about some of your best dating experiences. Feel free to drop in a comment or email me. Love is ALWAYS a beautiful thing.
Go well and with love good peeps.


