Last August, as I celebrated my fifth wedding anniversary, I quietly marked another anniversary of sorts: half a decade of searching, meddling, advising, consoling, celebrating—and worrying.

Shortly after I got married, I signed up to become a volunteer matchmaker on the popular dating Web site SawYouAtSinai.com.

When I began, I had planned on spending a few hours each week on the site perusing profiles and trying to find members who (quite literally) might click. For someone like me—a busy New York attorney forever glued to a laptop—it seemed like an easy mitzva: computer-based, and with none of the intensity and self-sacrifice of other outreach efforts, like visiting the sick or reading to the elderly at a nursing home.

Looking back at my time so far as an Internet shadkhan, I could not have anticipated how challenging matchmaking would be—or how fulfilling.

I was never the savviest single when it came to securing dates for myself. However, on SawYouAtSinai, where members are assigned to one or two matchmakers who try to connect them with other members, I discovered a knack for matching up others. A few months in, I celebrated my first engagement. Over the years, there were three more.

In the Jewish matchmaking world, an engaged match or two transforms you from a novice to a guru in the eyes of singles. Suddenly, every over-twenty Jewish professional and their cousin wanted my phone number. (Where were they when I was single?) But the truth is, some of my successful matches have come down to the most random of criteria. (Do not tell couple No. 3 this, but I matched them up mostly because they are both unusually tall.)

And some of my most brilliant match ideas never amounted to anything. For months, I coached Sue and Edwin, two forty-something New York Upper Westsiders who were crazy about each other but could not overcome their religious differences. Sue was adamantly Conservative; Edwin was intent on keeping a kosher, Sabbath-observant home. I was sure they belonged together and spent hours on the phone with Sue, trying to convince her that giving up shrimp cocktail and Saturday matinees was not such a big deal. Years later, Sue and Edwin are happily married to other people. Edwin married Sandy, an Orthodox woman who is perfect for him, and Sue decided to get back together with her ex. Mission accomplished, sort of.

And then there are those who seem like they will be impossible to match, like Ryan, the engineer who sounded so lonely and despondent when I talked to him on the phone that I almost recommended therapy. “I’m probably never going to meet anyone,” he said, and I secretly agreed.

Even the photo on his profile showed him looking miserable, complete with a gray sky and a somber-faced Ryan standing alone on a mountaintop. Miraculously, I found a young accountant from Baltimore who put a smile on Ryan’s face. They were married last June.

But that doesn’t stop me from occasionally losing sleep over Jason, a 40-year-old journalist who has been my SawYouAtSinai member since he was 35. Jason finds a way to sabotage every match I send his way. Getting him to the huppa has become something of a personal cause, though to do that I will have to find a way to get him past the first date.

Matchmaking is about building relationships, and surprisingly, those relationships don’t always involve two singles. Though it is my job to match them up, my members have also been the unwitting matchmakers between me and some of the most dedicated, inspirational men and women in the Jewish community—my fellow matchmakers.

I will never forget walking into a New York townhouse where a group of local matchmakers was to meet for the first of our monthly networking meetings. We were a mix of busy executives and young moms, and we were all in a rush to start our meeting so we could get home to our other responsibilities—until Ziva Kramer stopped us in our tracks. Kramer, a petite, soft-spoken relationship whiz known for her no-nonsense, empowering advice to single women, would not start the meeting—or any of our gatherings—without taking out her book of Psalms and reciting a stanza out loud. Whenever I get discouraged about all the couples I cannot seem to help, I remember Kramer’s prayer and remind myself that there is a Divine Matchmaker doing all the hard work, and I am only His conduit.

Everywhere I go I meet volunteers like Kramer who inspire me to continue my efforts. At a Seder in a Florida hotel last Passover, I got to talking with Tzipora Kloc, a dance instructor from Brooklyn who does not stop thinking about who she can set up next.

After a bitter divorce, Kloc spent years struggling to find love. When she finally remarried, Kloc opened her Shabbat table to singles of all ages and backgrounds and began networking tirelessly on their behalf. Though Kloc and I have yet to successfully make a match together, she and I are a great match; we have been e-mailing ideas back and forth to one another for over a year.

There is another unexpected benefit to working with singles. Over the years, as I have coached them to move past stereotypes and first impressions, I have challenged myself to do the same.

About three years ago, SawYouAtSinai decided to try something different—a real-life “meet the matchmaker” event. For the first time, I came face-to-face with the people who, until now, had existed in my world only as photos and biographies on a screen.

Sitting across the table from me, the singles were animated, nervous, funny and friendly. They had all the quirks and endearing qualities that an Internet profile can never fully get across. Almost none of them was exactly who I expected them to be, and every one of them was more interesting in real life than they appeared online. The guy who I always pictured as straight-laced and uptight turned out to be a boring profile writer but a charming talker. And the girl who I was sure would be average in appearance had an easy smile and a calming presence that made her seem prettier by the minute.

Meeting with members can be time-consuming and even draining, but I walk away from those meetings with a renewed hope and the sense that behind every profile, there is a real person with something to offer.

Still, for all the high points of amateur matchmaking, there has been much more failure. The ticker on the bottom left corner of my SawYouAtSinai screen tells me that I have suggested a total of 5,617 matches. Of those, only a small fraction agreed to talk on the phone, and only a small fraction of those ever went on a date. Sometimes I wonder if, among those 5,617 pairings, there are couples who are meant to be together and missed their chance. What if I had pushed a little harder?

People often ask me if I have received thank-you gifts from “my couples,” or if they have paid the traditional shadkhan’s gelt, which in some communities can amount to thousands of dollars. So far, with the exception of a fruit basket from one grateful couple, I have yet to be given anything tangible in return for the matches I made.

Which is not to say that I have not been rewarded for my efforts. Jewish folklore says that anyone who makes three matches gets a free pass to heaven. I do not know if this is true, but I do know it is a small piece of heaven as a shadkhan when you get the news that a couple you have introduced just got engaged. That is the moment when a matchmaker gets to look up from her laptop and say the two sweetest words in the Hebrew language: Mazal tov.

Shira Forman is an attorney and writer living in New York.