By Dr. Laura Docter
I was married for 19 years. At the time of my separation, my children were 6, 11, and 16. When the divorce was final, I knew I wanted a new life partner. I had not been on a date in 25 years! Aside from the requisite grit, resilience, and self-confidence, here are my eight learnings from online dating.
Lesson 1: Tell people you want to meet someone
A college friend, who was divorced several years before I was, told me to get on some dating apps. He warned that the process of choosing a date (or getting chosen) would be based more on looks than I would appreciate and that lots of people would pass me by for petty reasons. However, he encouraged me to give it a try, as there were many interesting 50-something singles out there. I ended up choosing Match.com.
Lesson 2: Investigate the people who reach out to you
Within 24 hours of creating my profile, I got a lovely note from a handsome man who had just come back from cycling in Bavaria and enjoyed racquet sports. He had me at, “Would you like to join me for lunch in the Stanford Rodin Garden?” With only his first name, profession, and hometown, I found him on Linkedin. His education and experience revealed that he was actually 73 years old, not 59—as his Match.com profile claimed. I needed to ask him about this discrepancy before I could go on a date. He responded that he would eventually tell me his real age, but since he played tennis with 50-year-olds, he thought he could “pass” for a while. I canceled the lunch as I wanted a relationship based on trust and truth-telling.
Lesson 3: Trust your date if they tell you that you are not the one
My first date was for an afternoon iced tea at Café Borrone. My date was attractive, polite, and attentive. He was also an experienced dater and gave me lots of tips, such as not inviting someone to dinner or drinks in the evening, sticking with daytime in coffee shops, and limiting the first meeting to 45 minutes. I had a lovely time, and I was pretty sure that when he offered to walk me to my car, he would ask me for a second date. However, he said, “I wish you all the best. We won’t be seeing each other again because I am looking for a red, and you are obviously a green, or maybe a blue.” I wondered what personality test he depended on to sort his potential dates. And, of course, I lamented the fact that I did not appear hot-blooded enough to satisfy his longing for “a red.” I awkwardly thanked him for the insight and drove away.
Lesson 4: Give your date your undivided attention and be curious about them–expect the same in return
I met another date at a small romantic Italian restaurant (he didn’t get the memo from the guy above about no dinners on the first date). We had corresponded in writing for some weeks while he was working in Amsterdam and I was on a family vacation, so we were both intrigued to get together in person. We ordered an appetizer, a primo, and a secondo—all to share. He listened generously, and he explained with clarity and passion. We were so wrapped up in each others’ stories and gaze, that the woman at the next table remarked as she left, “It’s so beautiful to see people your age still so obviously in love.” We smiled sheepishly and kept chattering away. I had found the connection I desired; however, the initial sparks soon faded.
Lesson 5: Ask about the important people in your date’s life
If you end up together, the people who are important to them will be your people, too. How your date treats their children, siblings, parents, and exes will likely become how they treat you. I went on four dates with a guy who was smart and interesting. We met for coffee on the patio at the Stanford Park Hotel, walked The Dish, had lemonade at Tressider Union, and ate lunch at the creperie by the train station. There just wasn’t any chemistry—or maybe he was extremely shy? Then we had a really intense discussion about his son, who had recently come out as a gay man. My date felt that he had not supported his young adult child appropriately and wanted to know what I thought he should do—since I spoke so lovingly about the close relationship I had with my queer child. This intimate discussion of parenting opened the gates to more personal questions and, ultimately, exposed that he was not a good fit for me.
Lesson 6: Set, and reset, the parameters for who you would like to date according to your honest assessment of your needs and values
When I first signed up on Match.com, I wanted to be open-minded about who I might meet and find exciting. I answered every question about my future date with the most accepting terms. I checked the boxes indicating I would date someone of any faith or no faith, of any color or nationality, tall or short, skinny or heavy. I did not require my date to have a college education, a specific career path, or a certain past. The only firm limitation was that I needed to date people who lived near me. I had kids and a job, so I could not commute. Then, one night, I got a message from a man with a profile that made me swoon. We liked the same country music artists; he had poems and quotations I appreciated on his profile and seemed humble and kind. Then I realized—oops, he’s from Oklahoma! In the middle of our texting, I wrote, “Wait, do you realize I’m in California?” He set the demographic qualities narrowly and the geographic locator as widely as possible. According to the descriptors featured, he had found 11 women in the entire country who were his “perfect matches.” It sort of creeped me out that ten other white women were 50 years old, 5’7”, with long blonde hair, a curvy athletic build, working in a helping profession, who had earned a Ph.D., were Protestant Christians of the progressive sort, who had children—and a yellow lab— and had been divorced. I wondered if the other women also liked canoeing, bicycling, skiing, horseback riding, beach walks, sunsets, and large dogs. I told the Oklahoma guy that if he ever made it to San Francisco, I would meet him in his “surrey with the fringe on top,” but he never made it to the city by the Bay.
Lesson 7: Own whether you are looking for a long-term, exclusive, committed relationship—or not.
I got a message from a man I knew of through mutual acquaintances, and we began seeing each other regularly. It was like he was an old friend and a sexy new date, all rolled into one. We had a fabulous time hiking, biking, dining, going to concerts, playing board games, and even planning a camping trip with our respective children. I thought I might have found “the one,” but he was clear from the beginning he was new to the dating scene and didn’t want something long term. He finally called it off, as he could tell I was falling too hard. I described my desire to be his one and only, and he described his romantic goals as “seeing lots of National Parks.” He loved Yosemite (that was me), but he longed to experience Glacier, Arches, the Smoky Mountains, and the Everglades. I cried a little, and my friends said some not-very-nice things about him, but I was thankful for a fun summer romance and the clarity it brought.
Lesson 8: Keep Hope Alive
Several weeks later, I decided to give Match.com one last try. That is when I met my husband! He said he knew after two or three dates. We have been together since 2014 and married since 2017. It feels like we are still on our honeymoon and are both so thankful to be each other’s second chance at love!
Dating over 50 is not for everyone. It was important to me as I wanted to find my life partner. The process taught me a lot and I hope it helps you if you wish to navigate this journey yourself.
Dr. Laura Docter is married to Cam Stout and currently curates a “portfolio life.” She serves on the advisory board of Cam’s non-profit, Stout Heart, Inc., teaches AP United States History at the Hun School of Princeton, cares for her darling granddaughters, and coaches clients who want to create health. Her business, As Yourself, is devoted to helping others achieve their goals – one healthy habit at a time. Laura loves visiting her children and her parents, going to Pure Barre class, cooking nutritious meals, soaking in her hot tub, and exploring new places.
Throughout this “Going It Alone” section of this blog, we will share learnings from others navigating retirement alone, so that you don’t have to do it all alone.