What Happened When I Said Yes To Every Guy That Asked Me Out

A few years ago, my “I’d date you” checklist went a little something like this: must be over six feet tall, have a glorious full beard, and wear tortoise shell glasses. He also had to have a stable career, boisterous laugh and posses the innate ability to hold a deep philosophical conversation without his eyes glazing over at the two minute mark. After finding a bunch of the tall, bearded guys weren’t what I’d thought they’d be, I decided to conduct a social experiment over the course of a few months and say yes to every guy that asked me out. Here’s what I learned:

  1. I realized that older guys are way more interesting than I gave them credit for. When I was asked out by a guy as old as my grandfather, I reluctantly agreed. Imagine my surprise when we had wonderful conversation — probably the best conversation I’d had in months. He was light-years ahead in the maturity department, and he had tons of stories to tell from his life experience. I didn’t say yes to a second date since we weren’t right for each other romantically, but I did enjoy gleaning wisdom from a more “experienced” man.
  2. I learned that I’d rather have a connection than a cute face. As I sat at the bar knocking back Jamie and Gingers and talking about life with a way younger guy, I realized that as mesmerizing as his eyes were and how chiseled his jaw was, there was literally zero real connection outside of the physical attraction.  A handsome face goes a long way, but it’s hard to have a heart to heart with someone who exists in a different reality.
  3. I realized what I was truly looking for. If I’d never dated outside my “type,” I wouldn’t have experienced all the nuances and subtleties that came along with guys of different personalities, age groups, and looks. Getting up close and personal with guys from all different walks of life allowed me to see what qualities worked for me and what didn’t long-term. That’s the biggest gift ever.
  4. I learned to trust my gut. Dating a broad selection of guys put me more in tune with my intuition. I used these dates as a kind of practice game for learning to trust myself: I could pretty much tell what was going to happen before we were five minutes in, and it was heartening when I was right. That doesn’t mean I pre-judged guys or didn’t give them a fair chance, but it’s good to have proof of how well I know myself and how I perceive people around me.
  5. I discovered that chemistry and an initial physical attraction are two different things. Have you ever met a guy who you weren’t attracted to at first, but then after interacting with him and talking to him more, you became absolutely smitten with him? Everything can look good on paper and a guy can fit your wish list perfectly, but if there’s no electricity in the air when you look into each others eyes, there’s no long-term potential.
  6. I learned not to judge a book by its cover. So many moments passed when I thought to myself, “This guy is nothing like I thought he’d be.” I realized my propensity to judge a guy based on looks, career, or social status said nothing of his character — in fact, it said way more about mine. I needed to get over myself. In the past, my overemphasis on looks had led me to ignore some definite red flags, but thankfully, that won’t happen anymore.
  7. I discovered I liked most about myself. I always considered myself shy and awkward in conversations, but going out with more guys than I wanted to exposed me to new opportunities to find myself. I learned that I had a lot to talk about when it came to my accomplishments, my beliefs, and my past. It’s definitely a confidence boost when you realize that you’ve gotten to a place in life where you’re actually a great catch. That boost made me feel like a million bucks.
  8. I realized my real dealbreakers. Before I widened my dating pool, I had a laundry list of reasons to call it quits with a guy who wasn’t 100% perfect in my eyes. Some of them were just preposterous, like lack of eye contact, a specific sense of humor, faulty grammar skills and dress sense (or lack thereof). I learned that foregoing some of my steep expectations was freeing and exciting. Quirks I once abhorred didn’t necessarily require a nail in the dating coffin, and it made dating much more fun.
  9. I learned the sacrifices I wasn’t willing to make. Sure, I learned that looks aren’t everything, but I also was able to more deeply examine what I loved most about my single life. When you’re dating lawyers one day and skateboarders the next, it really gives you the opportunity to explore what you’d have to potentially give up to be in a relationship with one of them. I’ve since dwindled down my dating pool again to dudes that represent more of what I’m looking for, but I can only do that since I took chances on guys who were totally wrong.
Lauren is a freelance writer living in New Jersey. When she's not deeply immersed in pondering the cosmos, you'll find her hiking a mountain, reading something philosophical, or dancing in her underwear. Read more of her existential musings at www.laurenvenn.com