top of page

Finding My Way in the World of Online Dating

By Lauren Sachs / Toledo, Ohio

The author's introduction to digital dating was sudden and unwanted

When I was suddenly widowed at age 46 in the early months of the pandemic, the last thing on my mind was modern dating. Prior to my loss, I had been in a happy and harmonious relationship with my husband Brad. While online dating was around when I met him some 20 years earlier, it was still regarded by some people as a somewhat fringe practice, almost an experiment of sorts for the tech savvy or those who had no luck finding love in the real world. My experience of meeting my husband could not have been more different . Brad and I met the “old-fashioned way”; not only was our first date an analog affair at a coffee shop, we had actually been set up through his mother. Now that’s what I call old school!

Given this history, you can imagine my trepidation about using technology to meet a potential partner. Obviously, my first order of business was coping with my grief and finding ways to help my children and I heal; therefore, I did not even consider dating until a whole year had passed. Still, the pandemic and my devastating loss led to intense feelings of loneliness, so the seed was planted in my mind fairly early on.

Even with my thoughts turning increasingly toward dating, I was highly resistant to trying online dating. While I knew many happy couples who had met via the Internet, on JDate (a Jewish dating site) in particular, I simply could not warm to the idea. Aside from friends who might approach the global subject of dating in a gentle manner, my therapist had been encouraging me to explore online dating specifically for many months.

Still, I held firm. Before exploring the digital dating world, I had a few close friends try and make introductions to other single acquaintances, reached out to some people from my past, and even tried a matchmaking service. None of these experiences led to anything meaningful. After my first real, but very brief, relationship as a widow came to an abrupt end, I finally relented to the idea of going online. Just like the pandemic accelerated the already increasing trend toward working from home, I realized that everyone seemed to be using online dating tools and avoiding this trend only hampered me further. We were all living so much of our lives virtually during the pandemic, it seemed like the only real way to proceed.

For me, the choice of which dating site to use was obvious since I was ideally seeking a Jewish partner for a long-term relationship. Once I decided to give JDate a try, I enlisted friends who could help me learn the ropes and get myself ready for my online debut. I had a photographer friend take some suitable, flattering photos and enlisted another close friend (a JDate veteran) to read over my “bio,” help me sign up, and learn about how to navigate the site.

Within my first few days on JDate. certain things jumped out at me right away. For example, I realized early on that some of the dating profiles were fake. I tried to figure out a method to differentiate which of my potential suitors were there seeking dates versus something more nefarious. I also learned the dating site lingo fairly quickly. One could send a “flirt” (a little emoji winking face); “like” another profile (by essentially pinning an emoji heart to the other person's profile); or even send a written message (similar to an email but only available to those with paid plans).

While I began to understand the rules of how to communicate, I could not help but think the use of the emojis seemed a little silly, particularly since I normally only used a winking emoji to be playful or suggest that something was funny. I also started to realize how much time one needed to devote to the site to keep up communication, since you could be talking and “flirting” with multiple people at the same time. It was like having a part-time job as a serial dater!

Aside from learning the basics, I started to notice trends on the site as well. Most activity occurred on Thursdays through Sundays, which makes sense given the average person’s work schedule. Given that it was a Jewish site, I was at first surprised to see that activity picked up around Jewish holidays, too. I wondered if this trend was due to the family-oriented nature of Jewish holiday celebrations, thinking that those festivities could be a reminder of how tough it was to be alone on such occasions.

Moreover, I discovered that many men completely disregarded my profile's clearly stipulated preferred age range of 40 to 58 years old. While I certainly received “flirts” and messages from men whom I considered age-appropriate, I received a shocking number of communications from men who were old enough to be my father. One particularly absurd message that arrived after an initial “flirt,” came from an older man with a biblical screen name and stated: “I would love to visit to have us meet in person, what is your closest hotel and airport to fly into?” To add to the absurdity, this man's photo suggested that he had been alive since biblical times as well.

Some men were much more direct and open about the obvious age difference between us but still persisted, even after I remained silent and did not respond to their queries, not wanting to mislead anyone about my intentions. In one specific instance, I had an older suitor follow up to my silence a month later. He stated how surprised he was that I was still on JDate considering how “gorgeous” I was and questioning whether my continued presence was because I could not choose amongst my many dating options or whether I was having too much fun dating multiple men. He went on to analogize my choice of men to picking an ice cream flavor and asking if I should be called “The 31 Flavors Woman.”

I also noticed that the older the potential suitor, the longer the message they sent. It seemed as though some of these older gentlemen thought that they could convince me to date a person outside my stated age range through a well-formed argument about our potential common interests and their worldliness. One man wrote a sort of mini-dissertation, ending his lengthy, autobiographical history and persuasive thesis with a quote from the Beatles song "In My Life." I believe he thought he could sway me by analogizing the lyrics to our future relationship.

While I will admit that some of this attention helped to rebuild my self-confidence after such a long time away from the dating world, I found some of the communication to be completely outlandish and laughable. I started to refer to myself as "catnip for older men" and had my own father in stitches as I related the antics of some of his contemporaries.

Another way in which my self-esteem received a boost was that I would occasionally also receive flirts and messages from men who were young enough to be my sons! One younger guy stated that I was "adorable" and suggested that I "skip the geriatrics" and go out with him instead. Another much younger man with whom I seemed to have a great deal in common reached out to me on multiple occasions, insisting that he could care less that I was 18 years older than him and wished I could see past our age difference. Once I did some calculations and realized that he was closer in age to my teenage daughter than to me, I was especially convinced that this was a nonstarter.

After chatting online long enough with a guy to determine that we could have some potential chemistry and mutual interests, the next conundrum was how to transition this virtual connection to the real world. Many men offered up their phone numbers while we were still chatting virtually. Still, the only way I felt comfortable arranging an in-person date was to first ask the man to share his last name. That way I was able to do some digging online via other social media sites and also check out professional postings and credentials.

I recall trying to make this research process a bit playful with a man who had already shared his phone number, telling him that I hoped he did not intend to continue on as “a man of mystery.” I was direct about my intention to google him, sharing that I was “a safety girl first and foremost” and had to make sure he was “not an axe murderer.” Even after my initial research showed no worrisome signs about a man, I always insisted on meeting in public. Oftentimes that meant a restaurant or coffee shop. No matter how lovely or romantic a walk in the park might ordinarily sound, I was not taking chances with my well-being.

In each instance where I agreed to meet for an in-person date, I was quite nervous when the day arrived. While I believe I possess a good degree of confidence, dating was a nerve-wracking proposition in and of itself, not to mention dating after 20 years away from the world of courtship. With online dating, it seemed like the initial virtual chatting helped ease some of the awkwardness one might experience with a blind date; however, some men seemed far more nervous than me.

One guy I met for an afternoon cup of coffee fidgeted so vigorously with the coffee cup sleeve that he essentially tore it to shreds during our conversation. Another incredibly accomplished gentleman I met for lunch surprised me with his obvious nerves. As we ate our lunch, I noticed that he had something akin to Invisalign on his upper teeth and he continuously moved it around in his mouth. This same gentleman was one of the few people I met whose online photos seemed to be rather outdated. While he still resembled the older posted photos, it was clear that he had changed quite a bit since they were taken.

My dating experiences were all varied but I definitely found some common themes. Fortunately, every man I met was respectful and courteous. I did not encounter anyone who had obviously lied on their profiles and was only met with one great surprise. On one date, a man shared that he had made a real error in judgment professionally which cost him both his job and his career in that profession. I was a bit shocked that he was so forthcoming on a first date about this huge mistake in his life, but I was also grateful for his honesty.

I soon learned that I had really solid intuition about the people I was meeting and it seemed obvious to me right away whether I should invest more time in getting to know them further. In one instance, I primarily dated a man through Zoom given the geographical distance between us. Though we got to know one another really well over the many months we were connecting online, I also realized for a variety of reasons that he made a far better friend than partner.

In the end, through my experience with JDate, I met a lot of great people and went on my fair share of dates with guys whom I found to be kind, intelligent, attractive, well-educated, and fun. Whenever I talk to other people who find themselves single, I share about my experience because it was really quite positive, and–frankly-–pretty entertaining. The best advice I can give to those who are considering online dating is to trust their intuition and take things slowly.

In my case, I eventually met someone on JDate who feels really special. While this man is obviously not like my late husband, the thing that stood out to me on our first date was how much I was reminded of my first date with Brad since they both somehow felt known to me right from the start. Losing my husband so suddenly and at such a relatively young age helped me understand that we get no guarantees in life. Still, I now know that love can be found at any age and in the most surprising places, even when we are highly resistant and even when the relationship starts with a winking emoji. 😉


Lauren Sachs has a BA in English and Psychology and a master’s degree in Social Work from the University of Michigan. After completing advanced clinical training at Yale, Lauren worked as a therapist and mental health consultant in a variety of settings. Once her daughters were born, Lauren’s career took an eclectic turn, including time as a fitness instructor and project manager. Lauren’s active role in the Toledo Jewish community led her to be the recipient of both the Harry Levison Young Leadership Award and the Shining Light Award. Currently, Lauren serves as a board member of the Jewish Federation of Greater Toledo and pens a monthly column about grief and personal growth for the Toledo Jewish News entitled “Happy Tears.” Lauren is also the author of a forthcoming book about Brad Sachs, her late husband, his joyful approach to life and work as an oncologist, and how examining his life helped her better cope with her grief.



bottom of page