wanna date my son?

A few weeks ago, I was in the back row of a crowded 7:30 pm yoga class. Just to be clear, this is not a flex and I am not good at yoga. Because I have trouble staying focused about 90% of the time, my mind tends to wander during exercise classes and I think about writing my next blog, to-do lists, what I am going to eat for dinner and who I can set up. In that 60 minute yoga class, I spent at least seven minutes thinking about the young woman in the row in front of me, guessing her age and whether she was single and might want to date my son. A week earlier, I had a similar experience where I took an immediate liking to a woman in my padel clinic, starting planning her life with my son and then was very disappointed to find out she was married with two kids. I know this is one of the weirder things that I do. Believe me. But, here’s the thing, I think about setting people up ALL of the time. I am a born matchmaker and I now realize that this is my passion, my calling and how I can leave my mark on this world.

I think it is important that I give you my matchmaking resume, starting with my two biggest home runs. With the help of my BFF Courtney, I set up Derek, a family friend whose dad was my mom’s favorite mixed doubles partner, with Tracey, a girl I had never met but was friends with Courtney’s co-worker and just happened to be Jewish and single. Derek and Tracey have been happily married since 2006 and have two kids. This setup was initiated by my mom who called me from Southern California to say that Derek had moved up to San Francisco and was there anyone I knew to set him up with. Remember that this was before Facebook, Match and Hinge, and when I asked Courtney if we knew anyone, she floated the possible set-up to some women in her office and one of them immediately suggested Tracey, who happened to be looking for a Jewish connection. It was not science – it was location and cultural identification and that’s it. But it worked.

My second successful match was also made mostly on a whim. In the early 2000’s, I was volunteering with an organization in the Bay Area that promotes discussion of public affairs. In one of the first meetings, I met another Board member who was single and seemed like a good guy. I was impressed that he was a doctor but had time to volunteer for something outside of his profession and was community-oriented. During the meeting, I distracted myself with how I planned to ask him if he would be open to being set up. I can’t remember exactly the wording I used but I left the meeting with his consent to potentially connect him with a single woman. That same week, I was at preschool pick up and ran into another mom and realized she was divorced and might be looking to date. She was literally the first single woman I ran into since meeting the eligible doctor and I just went for it and asked her if she would want to be set up. I gave her the limited information I had about the doctor and she was totally open to it. They dated for three years, moved in together, got married and had a baby. I lost touch with them several years ago but my understanding is that they are happily still together.

From these two experiences, there are basically three potential conclusions. One is that I am a gifted matchmaker who can see that two people will fit together purely based on gut instincts. The second is that I have too small of a sample size to prove that I am good at this. The third is that I am a total weirdo who, by the luck of the draw, happened to put two couples together over the last 20 years. I am choosing the first two explanations and running with it., Besides these two long time married couples, I have set up several other people who went on to date for a number of months and I consider those setups as matchmaking wins.  It should also be noted that I have gone deep in “The Millionaire Matchmaker” series and watched every episode of both “Indian Matchmaker” and “Jewish Matchmaker” on Netflix. Between my gut instincts and the time invested in “research”, I feel like I am approaching qualified professional status.

Case in point: In order to get first hand dating experience while being a married mother of two, I also “ghost dated” on Match.com for Courtney for six months in 2011.  As anyone who has tried online dating will tell you, it’s pretty awful. Yes, lots of people meet online but the vast majority find that it is a terrible experience where you spend a lot of time trading messages with people you never meet. While working undercover for Courtney on Match.com, I had a tough time finding anyone particularly interesting and eligible but did learn enough to write a 4-part series for a friend’s blog titled “Online Dating Tips.” I stand by my suggestions to this day. My top recommendations were: 

• Capitalize on being “new” to a dating site.
• Limit the number of emails and texts with prospective dates before you meet in person. 
• Include your friends in the process as a sounding board. 
• Refresh and rewrite your bio and photos, but always be brief.
• Choose sites where you have a competitive advantage.

For this last recommendation, I had encouraged Courtney to subscribe to ourtime.com, a dating site for people over 50, even though we were in our early 40’s at the time, because that would give her an edge over the other women. Similarly, I also felt there was a solid strategy to put her on jdate.com and list herself as a goy looking for a Jewish guy. She did not go for either of these ideas but I stand behind the strategic thinking of making yourself stand out in a large field of players. When asked to read this post before publishing, Courtney commented that she had no good reason at the time to reject this approach.

Consciously and unconsciously, I have been facilitating matches my entire adult life and I love doing it even though it does not always go well. My college roommate Allison recently reminded me that I set her up with one of my co-workers in 1993 solely based on the fact that they were both Catholic. He showed up to pick her up with a bumper sticker on the back of his car that said, “Kill Your TV” which made me realize before the date even started that I clearly knew nothing about this guy I was sending her out with. I am hoping she will let me redeem myself 30 years later now that she is on the market again. 

As I stood in that yoga class considering potential mates for my 25 year old son, I realized this passion has been 20+ years in the making. I hear so many of my friends talk about their adult kids in their 20’s who are looking to date and having a hard time meeting anyone they like. I have another gut feeling that if they all let me match them up, I could figure this out for them better than an algorithm. Unlike my single friends who are almost entirely female, my friends’ kids are equally male and female, never married and have no kids. So, I’m gonna throw it out there. If you are single and looking or know someone who is single, at any age, please send them my way. I’m gonna make a run at this.