10 Lessons Learned in a Year of Dating

I’m 31 and since I was 18, I’ve been in 3 relationships lasting 4 years, 7 months, and 6 years. Which means I never did a lot of casual dating and definitely not in the age of Social Media and dating apps. The two big relationships I had were with men who were extremely wrong for me. I naively believed if I loved them hard enough, I could make it work. All of the these facts culminated to one big challenge, I have a lot to learn regarding dating.

This year, I treated dating as exposure therapy with a “come what may” attitude. I signed up for online dating and accepted dates if the men came across as decent people. What resulted was first dates with 33 men this year. About a third of these men were met organically at events and through friends and in line waiting for tacos, and the rest were from online dating sites and dating apps. My goal was not only to possibly make a lasting connection with someone but also to learn all the things most people learn in their 20s that I didn’t learn. I want to learn what I want, what I need, what I don’t want, what I don’t need.

The whole experience has been fun, scary, exciting, eye-opening, humorous, humbling and surreal. I mean, I had my first first kiss in over six years and then a few more. I trespassed on private property on a second date. I tried dating a friend. I went out with engineers, writers, doctors, comedians, and a puppet maker. I ran into someone I was supposed to have a first date with the next day while giving my number to someone else. Someone asked me out while I was waiting for a date to arrive. I dated younger and older, poorer and richer. I hurt a few people’s feelings and had mine hurt. The range of experience in just a year was wide and varied.

Of course I took detailed notes to try make sense of it all and discover patterns. And here are just ten of the lessons learned.

  1. I learned meeting strangers or acquaintances over coffee or dinner gets easier and easier the more you do it. The first few first dates I’ve gone on, I’d fret about what I’m wearing and was sweaty with nerves up to the point of meeting them. In time, I found my prep before a date is now just reading a book or watching a show right before having to leave.
  2. I learned that the advantage of meeting people already vetted by your friends is you feel safe enough to let them pick you up for a date. Being picked up for a date adds a bit of magic to the date.
  3. I learned that I’m picky and that though I’m cautious and skittish, I’m not completely closed off like I feared. Of the 33 men, I was willing to pursue the possibility of a future with two of them. I had a huge crush on one the first quarter of the year and developed feelings for a second towards the end of the year. I was brave and I let someone in! I’m still standing!
  4. I learned that I’m scared of getting what I want and this manifests itself as nitpicking and making up superficial deal breakers. I have to be aware of any self sabotaging instincts and behaviors.
  5. I learned that I need a mix of intellectual conversation and play time. I want someone whom I can have long meandering conversations with that keep me engaged and someone who is willing to dance like penguins with me in the parking lot of a bowling alley. If you’re not willing to be stupid with me, it sets off alarm bells.
  6. I always try to treat people with care, but dating has really brought into light that though no one likes the sting of rejection, being the person rejecting is hard too. And I had to learn to carefully, honestly, and compassionately choose words when letting someone down. I learned that even if it’s easier to ignore text messages, sometimes there has been enough time spent together to make that uncomfortable conversation kind and needed.
  7. I learn that the people you casually date can also just become friends. I was under the impression that when you’re done, you’re done. I managed to keep some of the men I went on a few dates with as friends. This also hinged on the previous lesson. These friendships were made possible because I didn’t just disappear and forced myself to have those uncomfortable conversations.
  8. I learned being out and open can lead to happy accidents. I had a spontaneous first date with a stranger while reading a book in a coffee shop. He was brave and approached me and I didn’t have anywhere else to be and he seemed normal enough. We ended up having a conversation over coffee for over an hour.

  9. I learned my primary love language is definitely words. You can be attentive and give me gifts and do acts of services, and though I’m very appreciative of these actions, I don’t hear your message behind these kind acts unless they come with words. I very much need to hear or read actual words to register someone’s feelings towards me.
  10. I learned that though my goal is to find someone I can build a life with, I’m comfortable with the idea of living my life without a romantic partner. This feels like power. I can hold out for someone who is the best fit for me and don’t have to settle. I don’t have to settle because if I end up living my life alone, I’m confident I can make it a beautiful and happy one with my pursuits of adventure and with my friendships.

With the dawn of a new year looming, I’ve been reflecting on 2014. It has been a hard and amazing year and dating was a big life change in 2014. I’m curious to see what lessons in dating I’ll experience in the new year and remain hopeful that maybe 2015 is the charmed year when it comes to romance.

Tell me about some of your lessons learned while dating!

  • Kristen C

    Good for you. When I got divorced, I had much the same attitude about dating. I was definitely open to meeting people and tried so hard to keep an open mind, especially with dating profiles. I knew how weird the experience felt for me, so I knew that for the men I’d probably be interested in, they’d feel weird about it too, so tried to not have a profile or weird message drop a guy out of the possibility of a date. Your attitude about it all is the exact way to be, especially with the learning of things about yourself ( like me I learned I need a person who loves a night home watching internet cat videos just as much as one who wants a good sushi dinner). About a week from canceling my online dating profile, I met Q, the guy I have been with for 2 years in March. It happened because I was open to the experience of whatever happened. My whole attitude– “it’s going to take some great guy to take the place of no guy” ( as in my life by myself was turning out to be pretty awesome by itself). Huge hugs to you my friend.

    • Ah, Kristen your story gives me a lot of hope. :) I want to meet my Q.

      P.S. I hope our paths IRL crosses eventually. You’ve always been the kind of person I imagine I’d enjoy a cup of coffee with.

  • Yes, yes, yes! It’s been a pleasure having you as my sounding board when it comes to dating. And hearing about your dating adventures. It’s a tough world out there, and having someone to vent to it about is so helpful.

    What lessons have I learned? I think one of the biggest things I’m learning right now is that I need to be more open and more trusting. For the longest time, even though I’ve been ON online dating sites, I’ve had this negative feeling about it. I’ve discarded guys for SIMPLE things, like not using the best grammar or calling me “beautiful” in an OKC message. (That last one is still a pet peeve of mine, though…) I’m trying to trust the process more, stop letting fear dictate how I react, and to recognize that I am worthy of love and affection.

    Hugs to you! Let’s hope 2015 is the year we both find love. <3

  • I love how you’re so open to new things in your life and so introspective about those experiences. How much better the world would be if it had more people like you in it. :)

    • Jodi, you’re a kindred soul. <3

  • love this post so much, especially #10. :) what a great outlook!

  • this is a good list. thank you for sharing it with us =)
    i’ve learned that you do not have to follow any social norms for how the first date should go. a simple dinner, group meetup, or even geeky games, you have as much say as the other person as to how you meet each other for the first time

  • She’s growing up!!

    haha, I say that knowing I’m not as grown up as you…I tend to be the one to ignore text messages (bad habit, I know!!). You wrapped up this post eloquently with:

    “…I’m comfortable with the idea of living my life without a romantic partner. This feels like power. I can hold out for someone who is the best fit for me and don’t have to settle. I don’t have to settle because if I end up living my life alone, I’m confident I can make it a beautiful and happy one with my pursuits of adventure and with my friendships.”

    Yes, yes, yes. I’ve always believed this to be true.

  • FoodieIsTheNewForty

    Being introspective about your dating process is a huge step towards finding the right kind of partner for you. Have you read Keeping the Love You Find by Harville Hendrix? I read it about 20 years ago (when you were 11, ha ha!) so it may very well be dated and cheesetastic but I credit that book in part with helping me see that I was choosing men that were most definitely NOT right for me, why I was doing it, and eventually with helping me re-engineer my brain and heart to look for men who better fit my needs. I love you and am looking forward to witnessing future chapters of both of our lives together! And eating more cheesy shaved ice. :)

    • You mentioned this book to me before! I may have to put it on my list to read in 2015. :)

      I love you and can’t wait to live our lives together in the coming years! <3 I'm glad I already have a life partner in you!

  • love the list! and I totally agree that eventhough our ultimate goal is to find a life partner, sometimes it’s just good to go with the flow and not knowing what will happy next! and if it happens it happens :)

  • I read this with great interest. Really interesting and fun. How I admire this post, your honesty, and way of telling your story. “I learned that I’m scared of getting what I want…” struck a cord with me and it’s something I barely know how to “solve” yet. Awesome post :)

  • lisasyarns

    Wow, that is a lot of dates. Major kudos to you for putting yourself out there like that. It’s scary and hard and exhausting but it can be fun and rewarding and worth it all in the end. It does sound like you’ve learned so much over the past year, and could probably write a book but this top 10 list is great.

    I have been single so much of my life, it’s kind of crazy to think about. I had a serious high school boyfriend, casual boyfriends in college, and then 3 serious boyfriends in the last 10 years. But the longest relationship I’ve been in is my current one, although I don’t really know how to measure it because of our time apart when I was in Charlotte. I’ve also learned that I need words of affirmation. I’ve learned to speak up when something is bothering me – I used to not say something out of fear that the person would leave me. I’ve learned that I am the kind of person who needs my alone time and needs to maintain some sense of independence. And, lastly I’ve learned that everyone’s love stories are so different and that you can’t compare them and use the path others have taken as a litmus test for your own relationship.

    • Ah these are all great lessons! Thank you for sharing them.

      It’s really important for me to maintain my independence too, though I also need to cultivate a little dependence. I’m so used to my partners failing me and not being people I can depend on that I find it hard to have faith in people to show up!

  • My goodness, what an insightful post! I especially love #4, since I can see myself getting shortsighted by superficial dealbreakers too. My mom actually called me out on it [as in discussed], and we had serious conversations on why I set these arbitrary criteria. Although I hold firm with some of them, others can be overlooked and even be perceived as “the price of admission,” as someone said. It’s all a matter of trade off.

  • MJ

    #9. I like you.

  • DoanNut

    “Be brave. Take risks. Nothing can substitute experience.”
    – Paulo Coelho

    I think you lived up to that quote this past year.