I did it.
At long last, I have managed to return to “real” life. I am working full-time as a lawyer again. I am teaching spin classes, loving every moment of grueling sweatiness in front of a candlelit room. I have continued my volunteer work as an advocate, most recently attending the “End Well” conference in San Francisco, a day-long symposium focused on making the end of life experience more patient-centered. I am active in my recovery program, sharing my experience on how to get and stay sober with several beautiful young women. I am working with a personal trainer who challenges me at every one of our twice weekly meetings. I am regularly hiking trails that six months ago I could barely have completed. I remain focused on my spiritual practices, and though the attention they are given wanes occasionally, I don’t have to step too far out of line before I am gently (or violently, as the case may be) reminded of their necessity.
I am busy nearly all of the time. My life is full. I am content. I feel good about myself when I look in the mirror. I am so proud of the progress I have made, and so grateful that the Universe has seen fit to allow me to rejoin the human race.
So, naturally, it was also time to throw a wrench into the mix and start dating.
I had once dipped my toe into the online dating app world about a year and a half ago, and found the experience to be miserable. All the potential suitors I “matched” shared little in common with me, nor was I much attracted to them. I went out with one guy who half way through our second date started repeating stories, and I realized he had already reached the end of the “who am I” conversation. I was shocked – I mean, I wasn’t even through adolescence yet! The truth was, I simply was not yet ready at that point to date; the pain of losing my husband Patrick to brain cancer still too fresh. It was no wonder that everyone I found little or no connection with anyone. After a few terribly dry dates and a grand total of two weeks, I swore off dating apps for what I thought would be forever.
It all started just over a month ago. One of my close girlfriends told me she had just joined a dating app – and not just any dating app, but the very one that I had solemnly and a bit self-righteously declared myself too good for just a year prior. She shared with me the first few interactions, and they didn’t seem so bad. All that week I kept getting nods from the Universe that it was time to try again, which I first tried to ignore. Gradually, these nods became more persistent, and more obvious. “Really?!” I remember asking the Universe out loud. “Why on Earth would I subject myself to that nightmare again?” The answer, it seemed, was because it was time and there were lessons for me to learn.
That weekend, I was out to dinner with two of my closest friends, a couple who met on one of the most well-known dating apps. They were a great success story: completely in love, married, and expecting their first child. We started talking about dating, and how it might serve me to try and “put myself out there again.” Finally, I conceded that they had a point when they asked “What’s the worst that can happen? You don’t enjoy it, and you delete the app again.”
Somewhat begrudgingly, but with a notable hint of amusement, we downloaded the app on my phone during dinner. They picked out all the pictures I should use and helped me to keep my “profile” (read: sentence-long blurb without any real possibility of providing insight into who you are) light and funny. I am not sure why, but I didn’t expect to match with many people – but within a couple of hours, I had over a dozen connections. I was immediately overwhelmed! How was I supposed to manage talking to one person, let alone all of them?! I didn’t have the emotional bandwidth for that! Sensing my panic, my kind and patient friends told me not to worry, and that I did not have to talk to any of them if I didn’t want to. They reminded me that I was in charge, that I was the prize here, and that my self-worth was not tied to the outcome of any of these interactions. It was just what I needed to hear, and I took a deep breath, and said my first “hello’s.”
The very first guy I talked to was handsome, funny, and witty. He was also interested in meeting up in person right away which, although it caused me to take a hard gulp, I really appreciated because I honestly had no interest in texting some random person for weeks on end without it materializing into anything. I have real friends and real relationships for that! I also have zero interest in playing mind games with people, or wasting my time.
We set up our first date for the next day, and it went great. We talked for hours. There were a few things that gave me pause, but I tried to give him and the situation the benefit of the doubt. We went out again the next day. And the next. It was like a three-day long crack binge of attention that I had not experienced since the early days with Patrick. I also knew intuitively that it was completely unsustainable; no one could ever maintain that level of engagement because, you know, we have lives to live! I saw my historical pattern with relationships of jumping in with both feet without a life vest immediately repeating itself, and although I knew this was probably not going to turn out like I wanted to, but I went with it anyway. All I wanted was another hit.
It was not long before his true self started to be revealed. I realized that he had lied about several things, some really important, and some of those white lies that you don’t even know why someone bothers lying about because they don’t have to. Within a few weeks, I felt like I had been kicked in the teeth, and I knew there was no way that I could continue to see him without completely compromising my own integrity and self-worth. It felt crushing, because even though our interaction was so short-lived, it had been intense and in some ways amazing. I found myself wrought with disappointment. The desire to close my heart off again came strongly, but I refused to do so. I know the best way I can make amends to myself for the years of self-abuse and punishment is to remain open to whatever the Universe wants me to experience, no matter how long that is or how it turns out. Instead, I took my licks and kept moving.
One of the most important lessons I learned from that first experience was that I walked in as sort of a doe-eyed ingénue – I believed that because I have spent so much time working on myself and being comfortable with unapologetic authenticity, I made the incorrect assumption that the people I came in contact with were doing the same. It was naïve, and very far from the truth. Most people don’t spend as much time in their entire lifetime on a solitary self-appraisal as I have in the past year. Many don’t have the tools to handle stress and conflict in the healthy ways I have learned, which necessarily do not involve drugs or alcohol. This does not mean that I hold myself out as being above anyone else; rather, I just know that my self-awareness and desire for deep, soulful connection is not shared by not just the dating app population, but most of the world. And you know what? I am fine with that, because there is not a single part of me that feels like I need someone to be okay. I am no longer looking for validation. As I have shared in the past, I am not motivated by “checking the boxes” off of society’s mandated list of successes. I get to be 100% me, all the time. Take it or leave it. I’m good either way. What an incredible gift.
I have since been on a lot of dates. I have met some wonderful people. I have learned a ton about what I am really looking for in a partner. I have had experience in not just setting my own healthy boundaries, but holding them because I know that I am worth it. I have learned how to share my story about being a widow in a way that I am comfortable with. I am finding that it is the most refreshing feeling in the world to be able to share meaningful conversation with absolutely no attachment to where it may or may not lead.
I have also had several first date fiascos and strange interactions, which one would have to expect when engaging with perfect strangers. One person insulted me by suggesting I had too much time on my hands to respond to his messages. When I called him out for it, he tried to back peddle harder than Lance Armstrong and it rapidly devolved into a series of messages ending with "If you don't reply you're missing out on the best sex you ever had." I had one guy not only allow me to split the check (which, to me, is a faux pas if YOU asked ME on the date and it is the first time we are hanging out) but then spent five minutes figuring out how to divide the rest of it, after which he applied a gift card to only his portion of the bill. Another time, when a waiter asked if I wanted another drink and I politely declined, my date dismissed me and said "No, she'll have another" and proceeded to spend 30 minutes talking about motorcycles and muscle cars, barely pausing for breath. I just keep reminding myself that dating is one huge, weird social experiment, and that all of this experience is excellent material for a future book!
After losing Patrick, I did not know if I would ever be capable of connecting with people again. I now know that I am, and that it does not have to be scary because I don’t have to take it so seriously. On my 35th birthday last month, I celebrated with a single candle on my cake, because my wonderful friends reminded me I’m brand new again. I get a fresh start. It feels really, really good.
Lisa O'Leary is a lawyer, cat mom, widow, sports enthusiast, truth seeker, soul searcher, meditator, and consciousness practitioner who is actively engaged in quieting down the mind to allow the song to play.