Welcome to my blog. I document my twenty-something adventures and whims here. Hope you have a nice stay!

4 months, 20 dates, 5 lessons

4 months, 20 dates, 5 lessons

I’m sure you’ve been asked the question before, whether in a job interview or survey or self-questionnaire: what are you most proud of?

My initial reaction to this question is discomfort, for a few reasons. First, no matter how I answer the question I feel that I am a total brag. Second, feelings of inadequacy pop up - “will my answer be ‘enough’?”, “is this answer only coming from a place of privilege?”. Third, I haven’t figured out the depth of the emotions of pride and how it shows up in my life (how do you identify when you are feeling proud?).

I was lost in thought the other day, thinking back to last summer. My google photos reminded me that I was in Iceland this time last summer, so I browsed through all my photos again and had total wanderlust. And in my reflections of last summer, coupled with a strong sense lately of always wanting to learn and improve, I realized something I’m proud of. This answer would in no way suffice for a job interview but it felt good to identify something I’m proud of, that isn’t a big, audacious thing, like graduating college with top honors or starting a non-profit. 

Let me set the stage for this before I tell you what it is. It’s summer, I’m willingly unemployed for the time being, I’m living at home with my parents, and none of my friends from high school are around. I’ve got nothing but time on my hands for about 5 months. 

So what did I do?

I dated…a lot. 20 different guys, to be exact.


Since I had been in a relationship for quite some time, I hadn’t been in the dating game for almost two years. I’d never used any of the apps and had always met men through a common connection. The environment was perfect for upping my dating game, as I was leaving the area after the five months were up, had ample time, and a positive attitude. 

The first date I went on was with someone I sort-of knew, from high school. I knew the name when I first ‘matched’ with him and was reassured that he wasn’t a serial killer, which helped alleviate some of the pre-date jitters. I remember driving to the bar, sweating nervously (sexy, right?) while blasting my favorite song at the time for a pump up jam (Clearest Blue by CHRVCHES if you’re wondering). 

If you’ve ever gone awhile without riding a bike, you know that when you get back on you wobble and swerve until you remember how to balance yourself and peddle forward. The same goes for dating. If you haven’t done it in awhile, you swerve and misstep until you remember how to be a good dater - to ask thoughtful questions, listen closely, and examine body language, all while determining your level of interest. 

Back to the first date here. It was fine by all standards. Of course there were a handful of awkward moments, the bar we chose had an average age of 48, and I was still sweaty, but it was important for me to take on this challenge to get my dating skills back. Following our evening, he asked me out again and I agreed, and if I recall we went out a handful of times more. I quickly realized the attraction level was not there from my end and moreover, there were aspects of personality I did not vibe with. 

However, I will note that my traditional dating standards were tossed out the window during this experiment as I went into it with the idea that this would not result in a serious or long-term relationship. This gave me the opportunity to go out with men who weren’t traditionally my ‘type’. I dated men with different builds, backgrounds, and beliefs. Some were from the area, some from Europe,  some just visiting. Some were older, some were younger. There were common threads among most of the men (socioeconomically, prevalently). 

Over the course of about 4 months, I went out with about 20 different men. I even wrote their names down on a list on my phone with small nudges to help me remember each of them. If you do the math, that’s about a 1-2 men per week. I went out with some multiple times, and some I left in the middle of the date - I even had my dad rescue me by pretending he had a flat tire and calling me so I could walk out without being unkind. I went weeks without going out (due to travel, mostly), and scheduled dates back-to-back on the same night.

This ultimately became a fun social experiment for me, and served my initial purpose of boosting my dating skills. Let me try to summarize what I learned from the experiment:

  1. The best thing you can bring to dating is an open mind. I learned that I had to be generous in swiping and filter more heavily after conversing. If I axed every guy with tattoos, who had a hint of a dad bod, seemed short, wasn’t interesting, etc. I’d be left with maybe 3 guys, meaning that I’d only converse with 1 and maybe, just maybe, go out with one.
  2. Be creative and have fun with it.I had to be creative in my approach - testing out different opening lines, thinking of interesting questions that would get someone talking, and ways to stand out among thousands. Suggest something besides drinks if you want to go out with someone; ask him something besides “what’s up”. I went to the local history museum on a date (I didn’t even know we had one), I went to a Chance the Rapper concert where it felt like we were the only people over 21, I went to a local art festival, and I went kayaking downtown on the river. Drinks and dinner are great, but it’s also fun to change it up and do something totally new.
  3. Practice makes you betterBy the end of my dating experiment, I would go on a date and ponder what I was eating for my next meal and other mundane things rather than fret with nerves. It helped that the stakes were low, and I don’t want to downplay that I wasn’t looking for a partner through this process. Even so, I had no trouble sitting down with an internet stranger and talking about anything and everything. 
  4. Dating helps you recognize what you need and want in a serious partner. Although I had a notion in my head already of what an ideal partner embodies, this helped me further realize what were non-negotiable qualities and what I could compromise on. I learned what I needed to uncover to determine our compatibility (understanding his values, drivers, and aspirations) and how to uncover those in a tactful way.
  5. It is just a date. By going out with someone you aren’t committing to a life together, or even a second date. If it goes terribly, you likely won’t have to see the person again. If you do something embarrassing, so what? You’re not on a date with your childhood celebrity crush, and if he’s a good guy he won’t harp on it. If you explain your stories in a way that you feel doesn’t show you for who you truly are, try again on the next date. The (realistically) worst thing that can happen is you’ve lost a few hours of your time, perhaps some money, and maybe felt un-energized emotionally. 

There were some total flops along the way, though. I went out with someone who wouldn’t make eye contact the entire night, I had guys cancel while I was en route, I cancelled on guys due to pure laziness, I had guys ask me out on a second date where I had to turn them down (not fun!), and more. For every fun moment I had there was an accompanying awkward moment somewhere else along the journey - but that’s part of what made this such a great learning experience. 

What makes me proud of this all is putting myself out in the world and having the courage to be vulnerable and open to new experiences, even though it was uncomfortable, awkward, and tiring at times. I learned a lot along the way and had fun with it, and I’d recommend that if you get the opportunity to undertake a unique social experiment on yourself - go for it. 

A Gap in Emotional Vulnerability

A Gap in Emotional Vulnerability

Cheers to 23

Cheers to 23